Chestertown, Maryland Airbnb Market Data 2026: STR Report & Statistics
How much can you earn on Airbnb in Chestertown, Maryland? Based on AirROI's 2026 dataset (April 2025 – March 2026), the short answer is $38,518 per year — at a $378 nightly rate, 38.3% occupancy, and a $131 RevPAR that reflects a wider gap between nightly rates and realized revenue that rewards occupancy-focused strategies.
At 54 active listings, Chestertown is a boutique market where moderate demand with room for well-positioned listings to outperform. Supply grew 45.9% over the past year, yet revenue and nightly rates both trended upward — a signal that traveler demand is outpacing new inventory rather than being diluted by it. For hosts, pricing power remains intact even as competition increases.
Regulation is low with minimal registration requirements, pointing to an operator-friendly environment. In a market this size, differentiated listings with strong reviews can capture outsized returns relative to the competition.
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What Are the Key Airbnb Metrics in Chestertown?
In Chestertown, the headline Airbnb metrics are $38,518 in average annual revenue,38.3% occupancy, $378 ADR, and $131 in RevPAR, and guests book about 65 days in advance.
How Much Do Airbnb Hosts Earn Monthly in Chestertown?
Understanding the monthly revenue variations for Airbnb listings in Chestertown is key to maximizing your short term rental income potential. Seasonality significantly impacts earnings. Our analysis, based on data from the past 12 months, shows that the peak revenue month for STRs in Chestertown is typically July, while February often presents the lowest earnings, highlighting opportunities for strategic pricing adjustments during shoulder and low seasons. Explore the typical Airbnb income in Chestertown across different performance tiers:
- Best-in-class properties (Top 10%) achieve $7,743+ monthly, often utilizing dynamic pricing and superior guest experiences.
- Strong performing properties (Top 25%) earn $5,048 or more, indicating effective management and desirable locations/amenities.
- Typical properties (Median) generate around $3,085 per month, representing the average market performance.
- Entry-level properties (Bottom 25%) see earnings around $1,877, often with potential for optimization.
Average Monthly Airbnb Earnings Trend in Chestertown
What Is the Monthly Airbnb Occupancy Rate in Chestertown?
Maximize your bookings by understanding the Chestertown STR occupancy trends. Seasonal demand shifts significantly influence how often properties are booked. Typically, Julysees the highest demand (peak season occupancy), while February experiences the lowest (low season). Effective strategies, like adjusting minimum stays or offering promotions, can boost occupancy during slower periods. Here's how different property tiers perform in Chestertown:
- Best-in-class properties (Top 10%) achieve 71%+ occupancy, indicating high desirability and potentially optimized availability.
- Strong performing properties (Top 25%) maintain 54% or higher occupancy, suggesting good market fit and guest satisfaction.
- Typical properties (Median) have an occupancy rate around 37%.
- Entry-level properties (Bottom 25%) average 21% occupancy, potentially facing higher vacancy.
Average Monthly Occupancy Rate Trend in Chestertown
What Is the Average Airbnb Nightly Rate in Chestertown?
Effective short term rental pricing strategy in Chestertown involves understanding monthly ADR fluctuations. The Average Daily Rate (ADR) for Airbnb in Chestertown typically peaks in June and dips lowest during April. Leveraging Airbnb dynamic pricing tools or strategies based on this seasonality can significantly boost revenue. Here's a look at the typical nightly rates achieved:
- Best-in-class properties (Top 10%) command rates of $724+ per night, often due to premium features or locations.
- Strong performing properties (Top 25%) achieve nightly rates of $446 or more.
- Typical properties (Median) charge around $291 per night.
- Entry-level properties (Bottom 25%) earn around $208 per night.
Average Daily Rate (ADR) Trend by Month in Chestertown
What Is the RevPAR for Airbnb in Chestertown?
RevPAR in Chestertown is currently $131. Because RevPAR combines nightly rates with realized occupancy, it is one of the cleanest ways to compare how efficiently listings turn demand into revenue across the market.
- Entry-level properties (Bottom 25%) see $83 RevPAR.
- Typical properties (Median) generate $108 RevPAR.
- Strong performers (Top 25%) earn $175 RevPAR.
- Best-in-class (Top 10%) achieve $246 RevPAR.
Average Monthly RevPAR Trend in Chestertown
RevPAR Insights for Chestertown
- The average RevPAR in Chestertown is $131. This metric combines nightly rates with realized occupancy, making it one of the best single-number indicators of market efficiency.
- The gap between the top 10% ($246) and bottom 25% ($83) is $163, indicating significant performance disparity driven by property quality, pricing strategy, and location.
- RevPAR peaks in Jul and bottoms out in Mar, mirroring the broader seasonal demand pattern and suggesting opportunities for dynamic pricing.
Recommendations for Hosts
- Track your own RevPAR monthly against these Chestertown benchmarks. If your RevPAR falls below the median of $108, examine whether low occupancy or low ADR is the primary drag.
- Top-quartile listings achieve $175+ RevPAR through a combination of competitive pricing, strong reviews, and strategic amenities. Target this tier through incremental improvements.
- Use RevPAR rather than revenue alone when comparing properties of different sizes — it normalizes for available nights and gives a more accurate picture of performance.
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When Is the Peak Season for Airbnb in Chestertown?
Chestertown's peak Airbnb season falls in July, August, June, while the softest stretch is January, February, March. Overall, the market shows highly seasonal trends requiring careful strategy, which should guide pricing, minimum stays, and cash-flow planning.
Peak Season (July, August, June)
- Revenue averages $5,285 per month
- Occupancy rates average 47.9%
- Daily rates average $379
Shoulder Season
- Revenue averages $3,669 per month
- Occupancy maintains around 38.4%
- Daily rates hold near $363
Low Season (January, February, March)
- Revenue drops to average $2,739 per month
- Occupancy decreases to average 32.7%
- Daily rates adjust to average $357
Seasonality Insights for Chestertown
- Airbnb seasonality in Chestertown is pronounced. Revenue swings sharply between peak and low months, which means pricing strategy, minimum-stay settings, and cash reserves all need to account for extended slower periods.
- During the high season, the absolute peak month showcases Chestertown's highest earning potential, with monthly revenues climbing to $5,618, occupancy reaching 49.2%, and ADRs peaking at $385.
- Conversely, the slowest single month marks the market's lowest point — revenue may dip to $2,628, occupancy could drop to 31.9%, and ADRs may adjust to $342.
- Lower occupancy paired with meaningful seasonality means hosts in Chestertown need to maximize every peak-season booking and seriously consider whether off-season pricing adjustments or minimum-stay changes can capture incremental revenue.
Seasonal Strategies for Maximizing Profit
- Peak Season: Maximize revenue through premium pricing and potentially longer minimum stays. Ensure high availability and consider tightening cancellation policies to reduce last-minute gaps.
- Low Season: Offer competitive pricing, extended-stay discounts, and flexible cancellation policies. Target off-season travelers like remote workers, budget-conscious guests, and travelers with flexible schedules.
- Shoulder Seasons: Implement dynamic pricing that bridges peak and low rates. Target weekend travelers, local events, and business visitors. Slightly more flexible terms than peak season can help maintain occupancy without deep discounting.
- In a highly seasonal market like Chestertown, building a cash reserve during the top months is essential for covering fixed costs during the slow period. Automated pricing tools can help capture demand shifts in real time.
Do You Need a License for Airbnb in Chestertown?
Low regulation and minimal registration activity in Chestertown, Maryland, United States point to an operator-friendly environment. That said, even low-regulation markets may have tax collection requirements, safety standards, or HOA rules that affect short-term rental operations. Always verify the latest short-term rental regulations and Airbnb license requirements directly with local government authorities for Chestertown to ensure full compliance before hosting.
(Source: AirROI data, 2026, finding no licensed listings among those analyzed)
What Are the Best Neighborhoods for Airbnb in Chestertown?
Chestertown is a smaller vacation rental market where a handful of neighborhoods drive most of the booking activity. Choosing the right area is especially important in boutique markets — there is less room for a mediocre location to succeed on volume alone. The areas below highlight where short-term rental demand is strongest and why.
| Neighborhood / Area | Why Host Here? (Target Guests & Appeal) | Key Attractions & Landmarks |
|---|---|---|
| Historic Chestertown | Charming waterfront town with rich colonial history and beautiful historic architecture. Attracts visitors interested in history and small-town charm, making it ideal for cultural experiences. | Chestertown Historic District, Washington College, Custom House, Chestertown Farmers Market |
| Kent County | Picturesque rural area surrounding Chestertown, known for its scenic landscapes and outdoor activities. Ideal for nature lovers and those seeking relaxation away from urban life. | Chester River, Blackwater National Wildlife Refuge, Sassafras Natural Resource Management Area |
| Downtown Chestertown | The heart of the town, featuring quaint shops, restaurants, and art galleries. A perfect location for guests wanting to experience local culture and cuisine. | The Garfield Center for the Arts, The Blue Heron Cafe, Local art galleries |
| Eastern Shore Wine Country | Renowned for its wineries and vineyards. Attracts wine enthusiasts and those looking for a peaceful countryside getaway. | Crow Vineyard and Winery, 2021 Wine Festival, Chesapeake Wine Trail |
| Cannon Street | A historic residential area with Victorian-style homes and a close-knit community feel. Popular for family visits and those interested in heritage. | Historic homes, Local eateries, Chestertown's annual events |
| Riverfront Park | A scenic area by the river, perfect for outdoor activities and events. It draws visitors looking for recreation and scenic views. | Riverfront Park, Kayaking on the Chester River, Community events and festivals |
| Kent Narrows | A vibrant area with restaurants and access to boating and fishing. Great for visitors looking for waterfront dining and water activities. | Kent Narrows water access, Dining at waterfront restaurants, Fishing and boating opportunities |
| Rock Hall | A nearby small town known for its maritime heritage and outdoor activities. Perfect for those looking for a cozy retreat with water access. | Rock Hall Harbor, Local seafood dining, Maritime Museum, Chesapeake Bay access |
With 8 distinct neighborhoods showing meaningful short-term rental activity, Chestertown offers diversification within a single market. Investors can tailor their strategy — from high-turnover tourist zones to quieter residential areas that attract longer stays and remote workers.
What Types of Properties Are on Airbnb in Chestertown?
Room Type Distribution
Property Type Distribution
Market Composition Insights for Chestertown
- The Chestertown Airbnb market composition is heavily skewed towards Entire Home/Apt listings, which make up 94.4% of the 54 active rentals. This indicates strong guest preference for privacy and space.
- Looking at the property type distribution in Chestertown, House properties are the most common (66.7%), reflecting the local real estate landscape.
- Houses represent a significant 66.7% portion, catering likely to families or larger groups.
- The presence of 7.4% Hotel/Boutique listings indicates integration with traditional hospitality.
- Smaller segments like outdoor/unique, unique stays (combined 5.6%) offer potential for unique stay experiences.
Chestertown Airbnb Room Capacity Analysis (2026): Bedroom Distribution
Distribution of Listings by Number of Bedrooms
Room Capacity Insights for Chestertown
- The dominant room capacity in Chestertown is 3 bedrooms listings, making up 33.3% of the market. This suggests a strong demand for properties suitable for families or small groups.
- Together, 3 bedrooms and 2 bedrooms properties represent 51.8% of the active Airbnb listings in Chestertown, indicating a high concentration in these sizes.
- A significant 61.1% of listings offer 3+ bedrooms, catering to larger groups and families seeking more space in Chestertown.
Chestertown Vacation Rental Guest Capacity Trends (2026)
Distribution of Listings by Guest Capacity
Guest Capacity Insights for Chestertown
- The most common guest capacity trend in Chestertown vacation rentals is listings accommodating 8+ guests (44.4%). This suggests the primary traveler segment is likely larger groups.
- Properties designed for 8+ guests and 4 guests dominate the Chestertown STR market, accounting for 59.2% of listings.
- 61.1% of properties accommodate 6+ guests, serving the market segment for larger families or group travel in Chestertown.
- On average, properties in Chestertown are equipped to host 5.7 guests.
How Do Listings in Chestertown Compare on Quality?
Listing quality in Chestertown can be approximated through presentation depth, bedroom count, and how often hosts disclose exact locations. These signals show how professionally the local supply base is merchandised.
Listing Quality Insights for Chestertown
- At 39.1 photos per listing on average, Chestertown hosts invest well in visual presentation. Listings with 20+ photos consistently outperform in search ranking and conversion.
- 27.8% of listings show their exact location. Lower disclosure rates can increase booking hesitation — guests want to know exactly where they are staying.
Recommendations for Hosts
- Enable exact location if possible — it removes a common source of guest uncertainty and can improve your listing's position in map-based searches.
- Use these quality indicators as a self-audit checklist. Listings that exceed the Chestertown averages across all three metrics are better positioned for premium pricing.
What Amenities Do Airbnb Guests Expect in Chestertown?
Amenity Prevalence
Amenity Insights for Chestertown
- Essential amenities in Chestertown that guests expect include: Air conditioning, Heating, Smoke alarm, Wifi, Dishes and silverware, Kitchen, TV, Coffee maker, Microwave. Lacking these (any) could significantly impact bookings.
- Popular amenities like Hot water are common but not universal. Offering these can provide a competitive edge.
Recommendations for Hosts
- Ensure your listing includes all essential amenities for Chestertown: Air conditioning, Heating, Smoke alarm, Wifi, Dishes and silverware, Kitchen, TV, Coffee maker, Microwave.
- Prioritize adding missing essentials: Air conditioning, Heating, Dishes and silverware, Kitchen, TV, Coffee maker, Microwave.
- Consider adding popular differentiators like Hot water to increase appeal.
- Highlight unique or less common amenities you offer (e.g., hot tub, dedicated workspace, EV charger) in your listing description and photos.
- Regularly check competitor amenities in Chestertown to stay competitive.
Which Airbnb Amenities Boost Revenue in Chestertown?
Not every amenity matters equally. This table focuses on the amenities most associated with higher revenue in Chestertown, which makes it more useful for prioritizing upgrades than a simple popularity list alone.
| Amenity | Prevalence | Revenue With | Revenue Without | Revenue Uplift |
|---|---|---|---|---|
Cooking basics | 88.9% | $40,752 | $20,643 | 97.4% |
Washer | 85.2% | $41,110 | $23,616 | 74.1% |
Hot water kettle | 57.4% | $46,748 | $27,426 | 70.5% |
Barbecue utensils | 50.0% | $48,199 | $28,836 | 67.1% |
Bathtub | 50.0% | $47,973 | $29,062 | 65.1% |
Freezer | 66.7% | $44,202 | $27,149 | 62.8% |
Sun loungers | 16.7% | $56,551 | $34,911 | 62.0% |
Children’s books and toys | 24.1% | $54,024 | $33,601 | 60.8% |
Kayak | 25.9% | $53,087 | $33,418 | 58.9% |
Baking sheet | 64.8% | $44,244 | $27,969 | 58.2% |
Revenue Impact Insights for Chestertown
- Cooking basics tops the revenue impact list with a 97.4% uplift — listings with this amenity earn $40,752 vs. $20,643 without it.
- Cooking basics, Washer — while widespread — still correlate with meaningful revenue gains, making them table stakes rather than true differentiators.
Recommendations for Hosts
- Focus your upgrade budget on amenities in the top half of this table. Below-median amenities may improve guest experience but contribute less to revenue growth.
- Highlight revenue-impacting amenities prominently in your listing title, photos, and description — guests can't value what they don't notice.
Dive Deeper: Advanced Chestertown STR Market Data (2026)
Ready to unlock more insights? AirROI provides access to advanced metrics and comprehensive Airbnb data for Chestertown. Explore detailed analytics beyond this report to refine your investment strategy, optimize pricing, and maximize your vacation rental profits.
Explore Advanced MetricsChestertown Airbnb Guest Demographics & Profile Analysis (2026)
Guest Profile Summary for Chestertown
- The typical guest profile for Airbnb in Chestertown consists of primarily domestic travelers (91%), often arriving from nearby Washington, typically belonging to the Post-2000s (Gen Z/Alpha) group (50%), primarily speaking English or Spanish.
- Domestic travelers account for 91.3% of guests.
- Key international markets include United States (91.3%) and DC (6.6%).
- Top languages spoken are English (72.4%) followed by Spanish (7.1%).
- A significant demographic segment is the Post-2000s (Gen Z/Alpha) group, representing 50% of guests.
Recommendations for Hosts
- Target domestic marketing efforts towards travelers from Washington and Baltimore.
- Tailor amenities and listing descriptions to appeal to the dominant Post-2000s (Gen Z/Alpha) demographic (e.g., highlight fast WiFi, smart home features, local guides).
- Highlight unique local experiences or amenities relevant to the primary guest profile.
- Consider seasonal promotions aligned with peak travel times for key origin markets.
What Are Airbnb Guest Ratings in Chestertown?
Listings in Chestertown average 4.95 out of 5 overall, with about 86.4 reviews per active listing and 75.9% of listings carrying the Guest Favorite badge.
Rating Breakdown by Category
Guest Rating Insights for Chestertown
- With an overall rating of 4.95, Chestertown listings meet an exceptionally high bar. Guests consistently report strong satisfaction, which drives repeat bookings and referral traffic.
- The strongest subcategory is Communication (4.98), while Value (4.89) trails behind — a useful signal for hosts looking to prioritize upgrades.
- 75.9% of listings carry the Guest Favorite badge, a strong trust signal that can meaningfully lift click-through and booking rates.
Recommendations for Hosts
- Focus improvement efforts on Value — even small gains in the weakest subcategory can lift overall ratings and search ranking.
- Encourage guests to leave reviews after checkout. Listings with more reviews rank higher in search results and convert browsers into bookers more effectively.
Chestertown Airbnb Booking Patterns (2026): Available vs. Booked Days
Available Days Distribution
Booked Days Distribution
Booking Pattern Insights for Chestertown
- The most common availability pattern in Chestertown falls within the 181-270 days range, representing 42.6% of listings. This suggests many properties have significant open periods on their calendars.
- Approximately 79.6% of listings show high availability (181+ days open annually), indicating potential for increased bookings or specific owner usage patterns.
- For booked days, the 91-180 days range is most frequent in Chestertown (44.4%), reflecting common guest stay durations or potential owner blocking patterns.
- A notable 20.4% of properties secure long booking periods (181+ days booked per year), highlighting successful long-term rental strategies or significant owner usage.
How Far in Advance Do Guests Book Airbnb in Chestertown?
Average Booking Lead Time by Month
Booking Lead Time Insights for Chestertown
- The overall average booking lead time for vacation rentals in Chestertown is 65 days.
- Guests book furthest in advance for stays during May (average 111 days), likely coinciding with peak travel demand or local events.
- The shortest booking windows occur for stays in January (average 20 days), indicating more last-minute travel plans during this time.
- Seasonally, Fall (83 days avg.) sees the longest lead times, while Winter (28 days avg.) has the shortest, reflecting typical travel planning cycles.
Recommendations for Hosts
- Use the overall average lead time (65 days) as a baseline for your pricing and availability strategy in Chestertown.
- For May stays, consider implementing length-of-stay discounts or slightly higher rates for bookings made less than 111 days out to capitalize on advance planning.
- Target marketing efforts for the Fall season well in advance (at least 83 days) to capture early planners.
- Monitor your own booking lead times against these Chestertown averages to identify opportunities for dynamic pricing adjustments.
What Is the Average Length of Stay for Airbnb in Chestertown?
Guests in Chestertown stay about 3.9 nights on average, generating roughly 1,588 reservations and 29.4 bookings per listing in the latest AirROI dataset. The most common check-in time is 3:00 PM and check-out is 11:00 AM.
Monthly Length of Stay in Chestertown
Check-in Time Distribution
Check-out Time Distribution
Stay Pattern Insights for Chestertown
- A mid-range stay length points to leisure-driven demand — weekend getaways and short vacations. Hosts should optimize for quick turnover efficiency while keeping the guest experience smooth.
- At 29.4 bookings per listing, the turnover rate is high. Hosts with streamlined operations (self-check-in, automated messaging, reliable cleaners) have a structural advantage.
- Stay lengths peak in Jan (4.5 nights) and shorten in Oct (2.4 nights). Adjust minimum-night requirements seasonally to match.
Recommendations for Hosts
- With shorter average stays, focus on streamlining turnover. Self-check-in, reliable cleaning crews, and pre-staged amenities can reduce per-booking operational costs.
- Set your check-in time to match or beat the market standard of 3:00 PM. Offering early check-in flexibility can be a low-cost differentiator.
- Monitor length-of-stay seasonality to adjust minimum-night requirements — longer minimums during peak periods maximize revenue while shorter minimums fill gaps in shoulder seasons.
Chestertown Airbnb Minimum Stay Requirements Analysis
Distribution of Listings by Minimum Night Requirement
1 Night
9 listings
16.7% of total
2 Nights
24 listings
44.4% of total
3 Nights
6 listings
11.1% of total
30+ Nights
15 listings
27.8% of total
Key Insights
- The most prevalent minimum stay requirement in Chestertown is 2 Nights, adopted by 44.4% of listings. This highlights the market's preference for shorter, flexible bookings.
- A strong majority (61.1%) of the Chestertown Airbnb data shows acceptance of very short stays (1-2 nights), indicating a dynamic, high-turnover market.
- A significant segment (27.8%) caters to monthly stays (30+ nights) in Chestertown, pointing to opportunities in the extended-stay market.
Recommendations
- Align with the market by considering a 2 Nights minimum stay, as 44.4% of Chestertown hosts use this setting.
- If feasible, allowing 1-night stays, especially midweek or during low season, could capture last-minute bookings, as only 16.7% currently do.
- A 2-night minimum appears standard (44.4%). Consider this for weekends or peak periods.
- Explore offering discounts for stays of 30+ nights to attract the 27.8% of the market seeking extended stays.
- Adjust minimum nights based on seasonality – potentially shorter during low season and longer during peak demand periods in Chestertown.
Chestertown Airbnb Cancellation Policy Trends Analysis (2026)
Flexible
11 listings
20.4% of total
Moderate
14 listings
25.9% of total
Firm
22 listings
40.7% of total
Strict
7 listings
13% of total
Cancellation Policy Insights for Chestertown
- The prevailing Airbnb cancellation policy trend in Chestertown is Firm, used by 40.7% of listings.
- A majority (53.7%) of hosts in Chestertown utilize Firm or Strict policies, indicating a market where hosts prioritize booking security.
Recommendations for Hosts
- Consider adopting a Firm policy to align with the 40.7% market standard in Chestertown.
- Using a Strict policy might deter some guests, as only 13% of listings use it. Evaluate if potential revenue protection outweighs possible lower booking rates.
- Regularly review your cancellation policy against competitors and market demand shifts in Chestertown.
How Much Are Airbnb Cleaning Fees in Chestertown?
Cleaning fees in Chestertown are meaningful operating levers, not just pass-through charges. What matters most is how often hosts charge them, how high they run relative to market norms, and how large a share of gross revenue they consume.
Cleaning Fee Insights for Chestertown
- 77.8% of listings charge a cleaning fee, making it standard practice in Chestertown. Guests expect it and factor it into their booking decisions.
- The gap between the average ($174) and median ($150) cleaning fee indicates some high-end properties are pulling the average up considerably.
- Cleaning fees represent 10.4% of gross revenue on average — a significant line item that impacts total guest cost and competitiveness.
Recommendations for Hosts
- Price your cleaning fee competitively against the Chestertown median of $150. Fees significantly above market norms can deter bookings, especially for shorter stays.
- Consider whether bundling the cleaning fee into a slightly higher nightly rate might improve conversion, since many guests filter by total price and separate fees can feel punitive.
- Monitor competitor cleaning fees regularly. Airbnb's search algorithm factors in total price, so a well-calibrated cleaning fee can improve your listing's ranking.
What Do the Top Airbnb Listings in Chestertown Look Like?
Benchmark your potential! Explore examples of top-performing Airbnb properties in Chestertownbased on Trailing Twelve Month (TTM) revenue. Analyze their characteristics, revenue, occupancy rate, and ADR to understand what drives success in this market.
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Entire Place • 3 bedrooms
Piney Grove Farm
Entire Place • 5 bedrooms
Chestertown Watson Family Farm
Entire Place • 5 bedrooms
Down by the River
Entire Place • 3 bedrooms
Gorgeous home in town center & short walk to WAC
Entire Place • 5 bedrooms
River front cottage with private dock & water fun
Entire Place • 5 bedrooms
Note: Performance varies based on location, size, amenities, seasonality, and management quality. Data reflects the past 12 months.
Who Are the Top Airbnb Hosts in Chestertown?
Learn from the best! This table showcases top-performing Airbnb hosts in Chestertown based on the number of properties managed and estimated total revenue over the past year. Analyze their scale and performance metrics.
| Host Name | Properties | Grossing Revenue | Stay Reviews | Avg Rating |
|---|---|---|---|---|
| Matthew | 3 | $163,586 | 218 | 4.96/5.0 |
| Landon | 2 | $136,148 | 115 | 4.87/5.0 |
| Jennifer | 2 | $130,195 | 155 | 4.97/5.0 |
| Bob And Beth | 2 | $114,579 | 500 | 4.99/5.0 |
| Molly | 1 | $94,130 | 34 | 4.97/5.0 |
| Hannah | 3 | $84,419 | 133 | 4.99/5.0 |
| Beth | 1 | $81,244 | 50 | 5.00/5.0 |
| Caroline | 1 | $69,411 | 99 | 4.96/5.0 |
| John | 1 | $63,767 | 80 | 5.00/5.0 |
| Stephen | 1 | $62,228 | 4 | 5.00/5.0 |
Analyzing the strategies of top hosts, such as their property selection, pricing, and guest communication, can offer valuable lessons for optimizing your own Airbnb operations in Chestertown.
Who Are the Airbnb Hosts in Chestertown?
Chestertown is a quality-focused market, with a high Superhost share and fairly mature operating standards.
Host Profile Insights for Chestertown
- With 68.5% Superhosts, Chestertown has an experienced host base that sets high guest expectations. New entrants should plan for competitive quality standards.
- 3.7% of listings are professionally managed, reflecting a market still dominated by individual hosts.
- 0.0% of listings have Instant Book enabled. Lower Instant Book adoption means many guests must request approval, which can slow conversions.
- 79.6% of listings use Airbnb's simplified pricing (host-only fee), where the host pays the entire platform service fee and the guest sees one all-in price with no separate Airbnb service charge. High adoption signals a professional, PMS-connected host base — Airbnb mandates simplified pricing for software-connected listings.
Recommendations for Hosts
- Consider enabling Instant Book — it reduces booking friction and Airbnb's algorithm tends to favor Instant Book listings in search results.
- With 44.4% cohosted listings, there may be a growing local market for property management services.
- Benchmark your host metrics against these Chestertown averages regularly and adjust your hosting strategy based on what top performers do differently.
Top Professional Management Companies in Chestertown
These are the highest-grossing professional property management operations in Chestertown, ranked by total revenue across their portfolio. Their performance metrics offer a benchmark for what institutional-level hosting looks like in this market.
| Company | Listings | Revenue | ADR | Occ. | Rating |
|---|---|---|---|---|---|
| Landon | 2 | $136,148 | $637 | 39.8% | 4.87/5 |
Management Company Insights for Chestertown
- The leading management company, Landon, operates 2 listings with $136,148 in gross revenue — a useful benchmark for what scale looks like in Chestertown.
- Top managers average 2 properties each, suggesting professional management in Chestertown still operates at a relatively boutique scale.
- Professionally managed listings in the top tier average 4.87/5 in guest ratings — demonstrating that scale and quality can coexist.
Recommendations
- With only 3.7% of listings professionally managed, there may be an opportunity to differentiate through more structured operations and consistent guest experiences.
- Study how top management companies price, position, and maintain their portfolios — their ADR and occupancy rates reflect strategies refined across dozens of listings.
- If you're considering hiring a property manager, compare their portfolio performance against these benchmarks before committing.
How Does Chestertown's Airbnb Market Compare to Nearby Cities?
How does the Chestertown Airbnb market stack up against its neighbors? Compare key performance metrics like average monthly revenue, ADR, and occupancy rates in surrounding areas to understand the broader regional STR landscape.
Compared with Shannondale, Chestertown has 14 percentage points lower occupancy and about $29 higher ADR. That helps frame whether this market is winning more on demand, pricing, or both.
| Market | Active Properties | Monthly Revenue | Daily Rate | Avg. Occupancy |
|---|---|---|---|---|
| Polk Township | 15 | $6,885 | $537.97 | 35% |
| Centreville | 17 | $6,015 | $573.49 | 43% |
| Lemont | 21 | $5,793 | $914.83 | 38% |
| Shannondale | 45 | $5,722 | $348.96 | 52% |
| Hellam Township | 24 | $5,701 | $369.81 | 47% |
| Mayo | 13 | $5,615 | $489.21 | 50% |
| College Township | 83 | $5,467 | $869.23 | 37% |
| Stevensville | 79 | $5,306 | $574.06 | 41% |
| State College | 192 | $5,178 | $716.29 | 39% |
| Easton | 44 | $5,175 | $671.22 | 40% |
Frequently Asked Questions About Airbnb in Chestertown
These quick answers summarize the most common investor and operator questions using AirROI's latest market data for Chestertown.
How much do Airbnb hosts make in Chestertown?
Chestertown hosts earn about $38,518 per year on average, with an average nightly rate of $378 and RevPAR of $131. Those figures describe the typical revenue environment for active listings in Chestertown, Maryland, not the ceiling for the best operators. Source: AirROI 2026 data, Chestertown market, April 2025 to March 2026.
What is the average Airbnb occupancy rate in Chestertown?
The average Airbnb occupancy rate in Chestertown is 38.3%. July is the strongest month and February is the softest, so hosts should expect demand to move meaningfully throughout the year rather than stay flat.
What is the average Airbnb daily rate in Chestertown?
Listings in Chestertown average $378 per night. The broader pricing spread also matters: lower-performing listings cluster closer to the lower quartiles, while premium homes can price materially above the city average when demand spikes or listing quality stands out.
How many Airbnb listings are active in Chestertown?
Chestertown currently has about 54 active Airbnb listings in AirROI's market dataset. That supply count helps explain how competitive the market is, how much depth there is for benchmarking, and whether the market behaves like a niche destination or a scaled urban market.
How strict are short-term rental regulations in Chestertown?
AirROI currently classifies the short-term rental regulation level in Chestertown as Low. The dataset also shows about 0.0% of listings with registration evidence. That is a market signal, not legal advice, so hosts should still confirm current licensing and compliance rules locally before listing.
What is the RevPAR for Airbnb in Chestertown?
RevPAR in Chestertown is about $131. That metric combines pricing and occupancy into one efficiency number, so it is often a better quick benchmark than ADR alone when investors want to compare how well listings convert nightly rates into realized revenue.
Is Airbnb profitable in Chestertown?
Occupancy of 38.3% means Chestertown is a more selective market. Profitability is achievable but requires careful cost management, premium positioning, or targeting longer stays to reduce turnover. Average annual revenue is $38,518, but individual returns depend on property type, location within the city, and the host's operating efficiency.
How far in advance do guests book Airbnb in Chestertown?
The average booking lead time in Chestertown is about 65 days — a longer planning horizon typical of destination or vacation markets where travelers book well in advance. Hosts who understand their market's booking cadence can adjust minimum stays and pricing windows accordingly.
What are the best neighborhoods for Airbnb in Chestertown?
Based on AirROI's analysis, some of the top neighborhoods for short-term rentals in Chestertown include Historic Chestertown, Kent County, Downtown Chestertown. Each area attracts different guest profiles — from business travelers to leisure visitors — so the best location depends on the property type and target audience a host is aiming for. See the full neighborhood breakdown above.
What type of property performs best on Airbnb in Chestertown?
entire_home listings make up 94.4% of the active supply in Chestertown. The most common configuration does not always mean the most profitable — operators who identify underserved property types or bedroom counts can sometimes outperform the market average by filling a gap in local supply.
How does Chestertown compare to nearby Airbnb markets?
Among neighboring markets, Polk Township posts $82,623 in average annual revenue with 35.4% occupancy, compared to Chestertown's $38,518 and 38.3%. Comparing nearby markets helps investors understand whether a destination's performance reflects local demand or broader regional trends.
What is the average length of stay in Chestertown?
The average Airbnb stay length in Chestertown is about 3.9 nights. That matters for turnover, cleaning operations, and pricing strategy because shorter stays increase changeovers while longer stays can smooth occupancy and reduce operational friction.
What is the average Airbnb guest rating in Chestertown?
Airbnb listings in Chestertown average 4.95 out of 5 overall. About 75.9% of listings carry the guest favorite badge, which suggests a meaningful share of inventory is competing on review quality rather than price alone.
Which amenities boost Airbnb revenue in Chestertown?
Cooking basics and Washer are among the strongest revenue-linked amenities in Chestertown. In AirROI's latest dataset, listings with these amenities outperform those without on average revenue, which makes amenities analysis useful for prioritizing investment and listing upgrades.
Do Airbnb hosts charge cleaning fees in Chestertown?
Yes. About 77.8% of active Airbnb listings in Chestertown charge a cleaning fee, and the average fee is $174. The more important operating benchmark is how much of gross revenue that fee consumes, not just the absolute dollar amount.
What percentage of Airbnb hosts are Superhosts in Chestertown?
A 68.5% Superhost rate signals a highly competitive market where review quality and responsiveness are table stakes, not differentiators.
About AirROI Market Data
AirROI tracks over 20 million properties across 190+ countries and maintains 15+ years of historical performance data, making it one of the deepest Airbnb and STR intelligence platforms available. The analytics pipeline aggregates listing-level data monthly — revenue, occupancy, nightly rates, RevPAR, guest demographics, booking patterns, and competitive supply — so investors and operators can benchmark any market against its own history and against neighboring destinations.
Real estate investors, property managers, financial institutions, hedge funds, tourism boards, hospitality consultants, tech platforms, and academic researchers rely on AirROI data to underwrite acquisitions, optimize pricing, model macro trends, and conduct peer-reviewed research. Data is available through in-depth market reports like this one and the Airbnb API with 22 endpoints and an Airbnb MCP Server for AI agents.
AirROI proprietary analytics as of 2026-03-31. Metrics reflect trailing twelve-month aggregates from active listings. Revenue figures are market averages, not projections. Neighborhood descriptions are AI-generated and reviewed for accuracy. For full methodology, see the data methodology page.