Airbnb market data · 202512 months to October 2025
Winchester, CT Airbnb Market Data: Revenue, Occupancy & Trends
The average Airbnb in Winchester brought in $35,475 over the 12 months through October 2025, across just 18 active listings, so a single property can move that figure.
AirROI's latest figures for Winchester run through October 2025.
The short answer
Winchester Airbnb Market at a Glance
Listings averaged $338 a night and were booked on 41% of available nights.
Timing matters: in July, the best month, the average listing earned about 4.6 times as much as in March, the slowest. With only 18 active listings, a few bookings can reorder the months.
With 18 active listings, Winchester is the 12th-largest of 12 Northwest Hills Planning Region markets AirROI tracks.
Browse the live Winchester Airbnb market See Every Winchester ListingRevenue
How Much Do Airbnb Hosts Make in Winchester?
Gross bookings per Winchester listing averaged $35,475 over the 12 months to October 2025 (Northwest Hills Planning Region average: $40,956), before cleaning, platform and management costs and taxes.
The average Winchester listing brought in $7,560 in July, its best month, and $1,650 in March, its slowest. The three strongest months bring in 45% of a full year's revenue, where an even calendar would give any three months 25%.
Across Winchester's 18 active listings, monthly revenue by tier:
- Best-in-class properties (top 10%) earn $6,880+ a month, about three times the typical property.
- Strong performers (top 25%) earn $3,940 or more, roughly $1,700 a month above the median.
- Typical properties (median) earn about $2,290 a month.
- Entry-level properties (bottom 25%) earn $1,460 or less, about two-thirds of the median.
These are monthly figures for listings active in each month. The annual average above also counts listings that operated for only part of the year, so it runs below twelve times these figures.
July earned about 4.6 times what March did
Average revenue per active listing, by month
Winchester Airbnb Data by Month
Latest 12 months in the October 2025 data.
July led on revenue and bookings; nightly rates peaked in June.
| Month | Avg. Revenue | Occupancy | Avg. Nightly Rate | Booking Lead Time |
|---|---|---|---|---|
| Nov 2024 | $2,339 | 44.5% | $337 | 30 days |
| Dec 2024 | $3,215 | 42.5% | $329 | 38 days |
| Jan 2025 | $1,915 | 37.2% | $324 | 21 days |
| Feb 2025 | $2,618 | 36.7% | $319 | 27 days |
| Mar 2025 | $1,647 | 35.2% | $314 | 38 days |
| Apr 2025 | $2,208 | 32.2% | $319 | 55 days |
| May 2025 | $3,306 | 36.0% | $336 | 48 days |
| Jun 2025 | $4,513 | 49.8% | $369 | 71 days |
| Jul 2025 | $7,564 | 62.7% | $367 | 75 days |
| Aug 2025 | $7,233 | 55.8% | $366 | 78 days |
| Sep 2025 | $3,667 | 45.2% | $344 | 44 days |
| Oct 2025 | $2,722 | 46.2% | $326 | 36 days |
Averages per active listing in each month. Highlighted: the highest-revenue month. Booking lead time is the days between booking and check-in for stays in that month.
For a figure on one home rather than the whole Winchester market, enter its address and size in the Airbnb profit calculator, which compares it with similar listings nearby.
Profit
Is an Airbnb in Winchester Profitable?
Yes, when it's run well. The average Winchester Airbnb took in $35,475 in the 12 months to October 2025, and run by its owner at everyday costs, about $2,160 a month of that is left after running costs, so a home that costs less than that to own or rent makes money. A listing in the top quarter leaves about $3,740 a month.
These amounts come before housing costs. Where the mortgage or rent is less each month, the difference is profit; a home owned outright keeps it all after property tax, home insurance and any HOA or condo fees.
Winchester Airbnb Income, Expenses and Profit per Year
| Line | Average listing | Top-quarter listing |
|---|---|---|
| Money in | ||
| Gross bookings | $35,475 | $60,970 |
| Running costs | ||
| Airbnb's fee15.5% of bookings, Airbnb's standard host-only fee | −$5,500 | −$9,450 |
| Utilities and internetAbout 5% of bookings | −$1,770 | −$3,050 |
| Guest suppliesToiletries, coffee, paper goods: about 2% | −$710 | −$1,220 |
| Repairs and upkeepIncluding linens and small replacements: about 3% | −$1,060 | −$1,830 |
| Short-term rental insuranceOne policy, on top of Airbnb's free AirCover | −$350 | −$350 |
| Permit and registrationWhere one is required | −$180 | −$180 |
| Management$0 when you run it; co-hosts charge from about 10% of nightly bookings | $0 | $0 |
| Pricing and messaging toolsOptional; Airbnb's own tools are free | $0 | $0 |
| Lodging taxesAdded to the guest's bill and passed on | $0 | $0 |
| Total running costsAbout 27% of bookings | −$9,570 | −$16,080 |
| Left for housing costs, then profit | $25,905about $2,160 a month | $44,890about $3,740 a month |
| Housing costs | ||
| Mortgage or rent, property tax, home insurance, HOA or condo fees | Depend on the home | |
Estimate Your Own Winchester Airbnb Profit
The estimate starts from Winchester's average listing, run by its owner. Change how the listing performs, who runs it and who cleans to see what is left for the mortgage or rent.
To work out the profit on one Winchester home, with its price, its mortgage or rent and your own costs, use the Airbnb income calculator. It starts from the comparable listings around the address.
How Winchester's Top Earners Get There
- More nights booked. The busiest quarter of Winchester listings are booked on 63% or more of their nights, against 42% for the median listing. Ten more booked nights a year at the median rate of $175 adds about $1,760 in bookings.
- Prices that follow demand. Ranked by price, the top quarter charge $285 a night or more, against a median of $175. That is a separate ranking from the busiest quarter, so the two marks don't multiply into one listing's takings. For the average listing, a 10% higher rate on the nights it already books adds about $3,550 a year.
- Open for the busy months. July brought the average listing about $7,560, against $1,650 in March, so a calendar that is open and full in the busy months carries the year.
What a listing keeps comes down to the figures this page measures: nightly rate, nights booked and the months it's open. A listing at the top-quarter mark takes in about $5,080 a month, against $2,960 for the average one.
Occupancy
What Is the Airbnb Occupancy Rate in Winchester?
Winchester listings were booked on 41% of the nights they were open over the past year, 4 percentage points above the Northwest Hills Planning Region average (37%) and in line with the U.S. average. Occupancy swings from 32% in April to 63% in July.
Across Winchester's 18 active listings, the share of open nights booked by tier:
- Best-in-class properties (top 10%) are booked 74%+ of open nights, 32 points above the median.
- Strong performers (top 25%) fill 63% or more, roughly four nights a week.
- Typical properties (median) fill about 42% of open nights.
- Entry-level properties (bottom 25%) fill 26% or less, under two nights a week.
July was the busiest month in Winchester, April the quietest
Share of open nights booked, by month
The 12-month rate of 41% averages each listing's whole year, slow months included; each month here counts only the listings booked in it.
Nightly rates
How Much Does an Airbnb Cost per Night in Winchester?
The average nightly rate in Winchester, known as ADR (average daily rate), was $338 over the past year, about 19% below the Northwest Hills Planning Region average of $415 and about the same as the U.S. average ($335). Rates peak in June and July at about $370 and bottom out in February and March at about $315.
Across Winchester's 18 active listings, nightly rates by tier:
- Best-in-class properties (top 10%) charge $1,395+ a night, about 7.9 times the median.
- Strong performers (top 25%) charge $285 or more, about $110 above the median.
- Typical properties (median) charge about $175 a night.
- Entry-level properties (bottom 25%) charge $130 or less, about three-quarters of the median.
June rates ran 18% above March's
Average nightly rate (ADR), by month
Seasonality
Best and Worst Months for Airbnb in Winchester
With only 18 active listings, the monthly pattern in Winchester is noisy, since a few long or pricey stays can lift a month; revenue peaked in July and bottomed out in March.
How Far in Advance Do Guests Book Airbnb in Winchester?
Guests book Winchester stays 53 days ahead on average (about eight weeks). August stays are booked furthest out, about 78 days ahead, and January stays closest to arrival, about 21 days. A typical August booking is made in late May.
August stays are booked furthest ahead
Average days between booking and check-in, by month of stay
The 12-month figure of 53 days averages each listing's year as a whole; each month here averages only the listings with stays in it.
Permits
Airbnb Permits and Registration in Winchester
None of the 18 active listings in Winchester display a registration, permit or license number. That doesn't mean no rules apply: some places don't ask hosts to show a number on the listing, and listing data doesn't capture every scheme.
Registration, permit, zoning and occupancy-tax rules vary by address and change often, so confirm them with the city or county before buying or listing in Winchester.
Neighborhoods
Best Neighborhoods for Airbnb in Winchester
AirROI's area guide picks eight Winchester neighborhoods that draw short-term rental guests, led by Downtown Winchester, Winchester Historic District and Shawneeland. The picks reflect guest appeal, not earnings data or permit eligibility, so check local permit rules for a specific address before buying.
| Area | Who it suits | Landmarks nearby |
|---|---|---|
| Downtown Winchester | The vibrant downtown area is home to historic sites, shops, and restaurants, making it a popular choice for tourists looking to explore the local culture and history. | Old Town Winchester, Winchester History Museum, Abrams Delight, Museum of the Shenandoah Valley, Patsy Cline Historic House, Apple Blossom Mall |
| Winchester Historic District | This area showcases the city's rich history with beautiful architecture and is close to many historical attractions, attracting those interested in history and culture. | George Washington's Office Museum, Handley Library, Shenandoah Valley Discovery Museum, Old Court House Civil War Museum, Stonewall Jackson's Headquarters |
| Shawneeland | A serene, nature-filled neighborhood on the outskirts of Winchester, ideal for those looking for a retreat while still being close to the city. | Shawneeland Lake, Hiking trails, Parks and picnic areas, Nature conservation area |
| Berkeley | A suburban neighborhood offering a blend of residential comfort and convenience, making it ideal for families and long-term guests. | Local parks, Close to shopping, Community events, Family-friendly neighborhoods |
| Old Town | Known for its charming shops and restaurants, Old Town provides a delightful experience for visitors looking to enjoy local cuisine and entertainment. | Local dining experiences, Art galleries, Seasonal festivals, Live music venues |
| Cedar Creek | This area offers beautiful rural landscapes and outdoor activities, great for guests looking to escape the city life. | Cedar Creek and Belle Grove National Historical Park, Outdoor recreation opportunities, Scenic drives |
| Square Corner | A small community close to Winchester that offers a local feel and easy access to the city, suitable for short and long-term rentals. | Family-owned businesses, Close-knit community events, Access to local amenities |
| Meadow Branch | A growing neighborhood that appeals to both locals and visitors with its modern amenities and proximity to essential services. | Shopping centers, Local parks, Community features |
Area descriptions are AI-assisted from public sources and are not checked against zoning.
Nearby markets
Winchester vs. Nearby Airbnb Markets
Of the eight nearby markets in the table, all within 30 km, Litchfield (22 km away, 70 listings) earned the most per listing, about 46% more than Winchester.
| Market | Listings | Avg. annual revenue | Avg. nightly rate | Occupancy |
|---|---|---|---|---|
| Goshen 16 km | 32 | $42,313 | $406 | 36% |
| Litchfield 22 km | 70 | $51,688 | $423 | 41% |
| Cornwall 23 km | 38 | $46,613 | $371 | 39% |
| New Marlborough 27 km | 52 | $38,614 | $477 | 34% |
| Salisbury 28 km | 61 | $39,121 | $487 | 33% |
| Sharon 29 km | 38 | $39,750 | $335 | 41% |
| Bloomfield 30 km | 42 | $30,283 | $250 | 38% |
| Otis 30 km | 50 | $42,923 | $376 | 38% |
Other Airbnb Markets in Northwest Hills Planning Region
- Kent Airbnb data 35 listings
See all 12 Northwest Hills Planning Region Airbnb markets
Markets Similar to Winchester
Markets elsewhere in the United States with a similar nightly rate and occupancy to Winchester:
- Panama City Airbnb data FL · $340/night · 41.5%
- Ocean Pines Airbnb data MD · $339/night · 41.6%
- Treasure Island Airbnb data FL · $341/night · 41.0%
- New London Airbnb data CT · $335/night · 40.8%
- New Orleans Airbnb data LA · $340/night · 41.8%
- Norwalk Airbnb data CT · $335/night · 40.5%
FAQ
Winchester Airbnb FAQ
How much do Airbnb hosts make in Winchester?
An active Winchester Airbnb grossed $35,475 on average in the 12 months to October 2025, according to AirROI's tracking of 18 active listings. That is before cleaning, management, taxes and financing. Busier, better-run listings do far better: the top quarter took in $3,940 or more in a typical month.
How much can I make on Airbnb in Winchester?
It depends most on the home's size, location and how it's run. The middle half of Winchester listings earn between $1,460 and $3,940 in a typical month, and the top tenth $6,880 or more. For one home, enter its address and bedroom count in the Airbnb calculator: it compares the home with similar listings nearby.
What is the average Airbnb occupancy rate in Winchester?
Listings in Winchester were booked on 41% of available nights over the past year. That compares with 37% for the Northwest Hills Planning Region average. July was the busiest month.
How much does an Airbnb cost per night in Winchester?
The average booked night in Winchester cost $338 before fees. Half of listings charge between $130 and $285; a few high-priced homes pull the average above that range.
Do you need a permit for an Airbnb in Winchester?
None of the active Winchester listings display a registration, permit or license number. That doesn't mean no rules apply, so confirm registration, permit and occupancy-tax rules with the city or county before buying.
Is Airbnb profitable in Winchester?
Yes, when it's run well. The average Winchester Airbnb grossed $35,475 in the 12 months to October 2025, 13% below the Northwest Hills Planning Region average of $40,956, though with only 18 active listings a single property can move that figure. Run by its owner, with everyday costs for Airbnb's fee, utilities, supplies, upkeep and insurance, $25,905 a year (about $2,160 a month) is left before the mortgage or rent. A home that costs less than that to own or rent makes a profit, and a listing at the top-quarter mark leaves about $3,740 a month. Check a specific home in the Airbnb estimator.
When is Airbnb peak season in Winchester?
July paid best over the past year, at $7,560 per active listing, and March paid least. The month-by-month table above shows how rates and bookings each move.
How far in advance do guests book Airbnbs in Winchester?
Winchester stays were booked 53 days (about eight weeks) before arrival on average over the past year, so most of a month is booked well before it starts.
What are the best neighborhoods for Airbnb in Winchester?
Downtown Winchester, Winchester Historic District and Shawneeland draw the most short-term rental interest in Winchester. The neighborhood guide explains what brings guests to each.
How many Airbnbs are there in Winchester?
AirROI counted 18 active Airbnb listings in Winchester as of October 2025. The closest tracked market is Goshen, 16 km away.
Method
About This Data
Figures on this page cover 18 active Airbnb listings in Winchester from November 2024 to October 2025 (trailing twelve months). AirROI refreshes them monthly from listing-level booking and calendar data covering 20+ million properties worldwide. Money figures are in U.S. dollars. Annual revenue averages every listing active during the period, including those listed for only part of it; monthly figures average the listings active in each month; the tier lists show the spread. Neighborhood descriptions are AI-assisted. See the methodology for definitions.
Need this programmatically? The same metrics are available through the AirROI Airbnb Data API and bulk downloads in the data portal.