Airbnb market data · 202612 months to September 2026

Winchester, KY Airbnb Market Data: Revenue, Occupancy & Trends

Source: AirROI Reviewed by , Founder @ AirROI Updated

Active Airbnb listings
38
Avg. booking lead time
39 days
Listings showing a permit
0%
Peak revenue month
October
Lowest revenue month
January

The short answer

Winchester Airbnb Market at a Glance

Winchester is priced below the Kentucky average. Listings averaged $137 a night, about half that average of $250, and were booked on 40% of available nights, close to its 39% occupancy.

Timing matters: in October, usually the best month, the average listing earns about twice as much as in January, usually the slowest. With only 38 active listings, a few bookings can reorder the months.

With 38 active listings, Winchester is the 63rd-largest of 112 Kentucky markets AirROI tracks. From a year earlier, the number of active listings grew 6%.

Map of Airbnb listings in Winchester Browse the live Winchester Airbnb market See Every Winchester Listing

Revenue

How Much Do Airbnb Hosts Make in Winchester?

Gross bookings per Winchester listing averaged $16,186 over the 12 months to September 2026 (Kentucky average: $27,730), before cleaning, platform and management costs and taxes.

In a typical year, the average Winchester listing brings in $2,210 in October, its best month, and $1,120 in January, its slowest. The three strongest months bring in 30% of a full year's revenue, where an even calendar would give any three months 25%.

In a typical month, a top-quarter listing earns at least 3.6 times as much as a bottom-quarter one.

  • Best-in-class properties (top 10%) earn $3,800+ a month, about 2.4 times the typical property.
  • Strong performers (top 25%) earn $2,530 or more, roughly $970 a month above the median.
  • Typical properties (median) earn about $1,560 a month.
  • Entry-level properties (bottom 25%) earn $698 or less, about 45% 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.

October earns about twice what January does

Average revenue per active listing, by month, September 2024 to August 2026

Each point is one month as recorded, averaged over the listings active in it. The best and slowest months in the text average each calendar month over the past two years, so they can differ from the highest and lowest points here.

Winchester Airbnb Data by Month

Latest 12 months in the September 2026 data. September's figures are still coming in, so the rows run to August.

October 2025 led on revenue and bookings; nightly rates peaked in August 2026.

Average monthly Airbnb revenue, occupancy, nightly rate, RevPAR, booking lead time and length of stay per active listing in Winchester, Sep 2025 to Aug 2026
MonthAvg. RevenueOccupancyAvg. Nightly RateRevPARBooking Lead TimeAvg. Length of Stay
Sep 2025$2,09445.4%$134$7042 days3.9 nights
Oct 2025$2,50549.8%$141$8149 days4.2 nights
Nov 2025$1,47137.2%$134$4939 days4.4 nights
Dec 2025$1,18329.9%$130$3833 days3.2 nights
Jan 2026$1,09333.2%$127$3528 days5.6 nights
Feb 2026$1,13534.8%$126$4117 days5.4 nights
Mar 2026$1,83848.1%$130$5931 days4.6 nights
Apr 2026$1,93343.6%$137$6436 days5.6 nights
May 2026$1,89338.9%$144$6148 days3.3 nights
Jun 2026$2,14346.6%$146$7176 days3.4 nights
Jul 2026$2,25345.3%$147$7337 days4.8 nights
Aug 2026$2,37048.4%$151$7627 days4 nights

Averages per active listing in each month. Highlighted: the highest-revenue month of the 12. RevPAR is the month's revenue spread over its nights, booked or not. Booking lead time is the days between booking and check-in, and length of stay the nights per booking, for stays in that month.

The typical Winchester listing earns about $1,560 a month, but one property can land well above or below that. The Airbnb profit calculator gives a range for a specific address, built from the comparable listings around it.

Profit

Is an Airbnb in Winchester Profitable?

Yes, when it's run well. The average Winchester Airbnb took in $16,186 in the 12 months to September 2026, and run by its owner at everyday costs, about $880 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 $1,440 a month.

Cleaning it yourself keeps the $1,600 a year guests pay in cleaning fees, for about $1,010 a month. Handing the listing to a co-host at about 10% of nightly bookings still leaves about $760 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

A year of income, running costs and what is left for housing costs for an average and a top-quarter Winchester Airbnb
LineAverage listingTop-quarter listing
Money in
Nightly bookings$14,586$23,630
Cleaning fees guests pay10% of Winchester bookings$1,600$2,600
Gross bookings$16,186$26,230
Running costs
Airbnb's feeAbout 14%: 15.5% for the 84% of Winchester listings on Simplified Pricing, 3% for the rest−$2,190−$3,550
Cleaning and laundryPaid for by the cleaning fee; $0 if you clean yourself−$1,600−$2,600
Utilities and internetAbout 5% of bookings−$810−$1,310
Guest suppliesToiletries, coffee, paper goods: about 2%−$320−$520
Repairs and upkeepIncluding linens and small replacements: about 3%−$490−$790
Short-term rental insuranceOne policy, on top of Airbnb's free AirCover−$160−$160
Permit and registrationWhere one is required−$80−$80
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 25% of bookings, plus cleaning paid for by the cleaning fee−$5,650−$9,010
Left for housing costs, then profit$10,536about $880 a month$17,220about $1,440 a month
Housing costs
Mortgage or rent, property tax, home insurance, HOA or condo feesDepend 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 65% or more of their nights, against 38% for the median listing. Ten more booked nights a year at the median rate of $125 adds about $1,240 in bookings.
  • Prices that follow demand. Ranked by price, the top quarter charge $185 a night or more, against a median of $125. 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 $1,460 a year.
  • Open for the busy months. In a typical year, October brings the average listing about $2,210, against $1,120 in January, so a calendar that is open and full in the busy months carries the year.
  • Reviews that stand out. Winchester listings average 4.81 stars, and 55% carry Airbnb's Guest Favorite badge, which guests can filter for.

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 $2,190 a month, against $1,350 for the average one.

Occupancy

What Is the Airbnb Occupancy Rate in Winchester?

Winchester listings were booked on 40% of the nights they were open over the past year, in line with the Kentucky average and in line with the U.S. average. In a typical year, occupancy climbs to 52% in October and falls to 33% in January.

The busiest tenth of listings are booked about 5.3 times as often as the bottom quarter.

  • Best-in-class properties (top 10%) are booked 81%+ of open nights, 43 points above the median.
  • Strong performers (top 25%) fill 65% or more, roughly five nights a week.
  • Typical properties (median) fill about 38% of open nights.
  • Entry-level properties (bottom 25%) fill 15% or less, under two nights a week.

October is usually the busiest month in Winchester, January the quietest

Share of open nights booked, by month, September 2024 to August 2026

The 12-month rate of 40% 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 $137 over the past year, about 45% below the Kentucky average of $250 and about 57% below the U.S. average of $320. In a typical year, rates peak in June and August at about $140 and bottom out in February and December at about $125.

The top 10% charge about 2.9 times the rate of the bottom quarter.

  • Best-in-class properties (top 10%) charge $230+ a night, about 1.9 times the median.
  • Strong performers (top 25%) charge $185 or more, about $60 above the median.
  • Typical properties (median) charge about $125 a night.
  • Entry-level properties (bottom 25%) charge $81 or less, about two-thirds of the median.

June rates run 14% above February's

Average nightly rate (ADR), by month, September 2024 to August 2026

What Is the RevPAR for Airbnb in Winchester?

RevPAR, or revenue per available night, divides a listing's income by every night it was open to book, so it rises with both price and bookings. In Winchester it averaged $57 over the past year, from about $36 in a typical January to about $71 in a typical October.

Per open night, by tier:

  • Best-in-class properties (top 10%) earn $128+ per open night, about 2.3 times the median.
  • Strong performers (top 25%) earn $70 or more, about $14 a night above the median.
  • Typical properties (median) earn about $56 per open night.
  • Entry-level properties (bottom 25%) earn $40 or less, about three-quarters of the median.

October RevPAR is about twice January's

Revenue per open night (RevPAR), by month, September 2024 to August 2026

Seasonality

Best and Worst Months for Airbnb in Winchester

With only 38 active listings, the monthly pattern in Winchester is noisy, since a few long or pricey stays can lift a month; revenue has tended to peak in October and bottom out in January.

Average revenue by month in Winchester

Average revenue per active listing, each calendar month averaged over the past two years

Revenue by month in Winchester in numbers
Average monthly revenue per active listing in Winchester, by calendar month
MonthRevenue per listing
January$1,120
February$1,350
March$1,790
April$1,970
May$1,870
June$2,100
July$2,070
August$2,080
September$2,080
October$2,210
November$1,460
December$1,200

How Far in Advance Do Guests Book Airbnb in Winchester?

Guests book Winchester stays 39 days ahead on average (about six weeks). June stays are booked furthest out, about 57 days ahead, and February stays closest to arrival, about 15 days. A typical June booking is made in mid-April.

June stays are booked furthest ahead

Average days between booking and check-in, by month of stay, September 2024 to August 2026

The 12-month figure of 39 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 38 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 Historic Downtown, Cedar Creek Lake and Buffalo Trace Distillery. The picks reflect guest appeal, not earnings data or permit eligibility, so check local permit rules for a specific address before buying.

Best neighborhoods for Airbnb in Winchester
AreaWho it suitsLandmarks nearby
Historic DowntownCharming area with rich history and beautifully preserved architecture. It attracts visitors looking for cultural experiences and local dining.Bluegrass Heritage Museum, Clark County Courthouse, Winchester Opera House, Local shops and restaurants, Artisans and crafts fairs
Cedar Creek LakeScenic area popular for outdoor activities like fishing, boating, and hiking. Ideal for nature lovers and families seeking recreation.Cedar Creek Lake, Cedar Creek Park, Local hiking trails, Fishing spots, Picnic areas
Buffalo Trace DistilleryFamous bourbon distillery offering tours and tastings. A must-visit for bourbon enthusiasts and those interested in local culture.Buffalo Trace Distillery, Bourbon tasting experiences, Distillery tours, Historic landmarks nearby
Southeast WinchesterResidential area with proximity to parks and schools. Great for families visiting or relocating to the area.Local parks, Schools and community centers, Family-friendly neighborhoods, Shopping centers
Winchester Industrial ParkStrategically located for business travelers and those visiting local businesses and factories. Suitable for extended stays for work-related trips.Industrial facilities, Proximity to major highways, Corporate offices
College Park AreaHome to local colleges, attracting students and visiting families. Ideal for short-term rentals during the academic year and events.Local colleges, Student activities, Community events, Nearby cafes and shops
The Red River GorgeNatural area with stunning cliffs and rock formations, popular among adventure seekers and hikers. Great for eco-tourism.Red River Gorge, Natural Bridge State Resort Park, Hiking and climbing spots, Scenic views
Cultural Arts DistrictVibrant area with arts programs and events. Attracts visitors interested in arts, culture, and local community events.Local art galleries, Theater and performance venues, Art festivals, Craft fairs

Area descriptions are AI-assisted from public sources and are not checked against zoning.

Listings

Winchester Airbnb Listings by Type and Size

Every Airbnb in Winchester is an entire home: all 38 listings rent the whole place. Houses are the most common property type at 34%, ahead of cabins and other outdoor stays (29%).

Every listing rents the whole place

Winchester Airbnb listings by room type

  • Entire home 100%
Room types in numbers

Listings by property type

Winchester Airbnb listings by property type

  • House 34%
  • Cabin/Outdoor 29%
  • Apartment/Condo 29%
  • Hotel/Boutique 8%
Property types in numbers
Winchester Airbnb listings by property type
Property typeShare of listingsListings
House34.2%13
Cabin/Outdoor28.9%11
Apartment/Condo28.9%11
Hotel/Boutique7.9%3

How Many Bedrooms Do Airbnb Listings in Winchester Have?

One-bedroom homes are the most common size in Winchester (46% of entire homes), followed by two-bedroom homes (30%).

Winchester entire homes by number of bedrooms

Entire homes with each number of bedrooms

Bedroom counts in numbers
Winchester entire homes by number of bedrooms
BedroomsShare of entire homesEntire homes
1 bedroom45.9%17
2 bedrooms29.7%11
3 bedrooms13.5%5
4 bedrooms10.8%4

What Each Home Size Earns in Winchester

A typical one-bedroom home in Winchester earned $11,200 over the past year, against $14,100 for a two-bedroom home.

What each home size earns in Winchester
Home sizeListingsTypical annual revenue (median)Average annual revenueAvg. nightly rateOccupancy
1 bedroom17$11,200$11,700$9140%
2 bedrooms11$14,100$16,600$15539%

How Many Guests Do Airbnbs in Winchester Sleep?

Most Winchester listings are sized for couples and small families: 61% sleep four guests or fewer, and just 11% take eight or more.

Winchester listings by guest capacity

Share of listings by the number of guests they sleep

Guest capacity in numbers
Winchester listings by guest capacity
Guest capacityShare of listingsListings
2 guests15.8%6
3 guests10.5%4
4 guests34.2%13
5 guests7.9%3
6 guests18.4%7
7 guests2.6%1
8+ guests10.5%4

How Winchester Airbnb Listings Are Set Up

Winchester hosts set up an average of 2.4 beds per listing, close to one bed per bedroom. Only 42% of listings show their exact location on the listing map; the rest show an approximate area.

Photos per listing
14
Beds per listing
2.4
Show exact location
42%

What Amenities Do Airbnb Listings in Winchester Offer?

Fire pits are common in Winchester: 42% of listings have one, and 95% offer free parking on site.

Share of Winchester listings with each common amenity

  • TV 97%
  • Smoke alarm 97%
  • Heating 97%
  • Air conditioning 97%
  • Free parking on premises 95%
  • Dishes and silverware 89%
  • Coffee maker 87%
  • Dedicated workspace 84%
  • Hot water 84%
  • Bed linens 84%

Guests

Who Books Airbnbs in Winchester?

Winchester draws mostly domestic guests: 97% of those who left reviews live in the United States. No single city dominates: Lexington is the largest source outside Winchester, at about 5% of reviews.

97% of Winchester guests are domestic

Where guests who left reviews live

  • Domestic 97%
  • International 3%

Where Winchester guests come from: top cities

Share of guests who left reviews

  • Lexington 5%
  • Cincinnati 3%
  • Louisville 2%
  • Chicago 2%
  • Winchester 1%
Top origin cities in numbers
Where Winchester guests come from: top cities
Origin cityShare of guests
Lexington4.9%
Cincinnati2.9%
Louisville2.0%
Chicago1.7%
Winchester1.4%

Where Winchester guests come from: top countries

Share of guests who left reviews

  • United States 97%
  • Canada 1%
  • United Kingdom 1%
  • Brazil 0%
Top origin countries in numbers
Where Winchester guests come from: top countries
Origin countryShare of guests
United States97.1%
Canada1.4%
United Kingdom0.6%
Brazil0.3%

Languages spoken by Winchester guests

Share of guests who left reviews

  • English 81%
  • Spanish 8%
  • Portuguese 3%
  • French 3%
  • Chinese 2%
Top languages in numbers
Languages spoken by Winchester guests
LanguageShare of guests
English81.4%
Spanish7.7%
Portuguese3.2%
French2.6%
Chinese1.9%

What Are Airbnb Guest Ratings in Winchester?

Winchester Airbnbs average 4.81 stars, and 55% of listings hold Airbnb's Guest Favorite badge. The category scores are tightly bunched, and cleanliness is the lowest, at 4.80. Listings here carry long review histories, about 110 reviews each on average.

Communication scores highest in Winchester; cleanliness is lowest

Average guest rating out of 5 by category; the bars start at 4.0

  • Accuracy 4.86
  • Cleanliness 4.80
  • Communication 4.92
  • Location 4.84
  • Check-in 4.91
  • Value 4.81
Category scores in numbers
Winchester guest ratings by category
CategoryAverage rating (out of 5)
Accuracy4.86
Cleanliness4.80
Communication4.92
Location4.84
Check-in4.91
Value4.81

Booking patterns

How Guests Book in Winchester: Stays, Rules and Fees

About seven in ten Winchester listings are open to guests more than 180 days a year, but only 29% are booked or blocked that many days. The most common booked-or-blocked total is 31 to 90 days a year, covering 34% of listings; blocked nights include any the host closes off.

Days a year Winchester listings are open to guests

Share of listings by days a year

  • 271-366 days 47%
  • 181-270 days 24%
  • 91-180 days 26%
  • 31-90 days 3%
Open days in numbers
Days a year Winchester listings are open to guests
Days a yearShare of listingsListings
271-366 days47.4%18
181-270 days23.7%9
91-180 days26.3%10
31-90 days2.6%1

Days a year Winchester listings are booked or blocked

Share of listings by days a year

  • 271-366 days 3%
  • 181-270 days 26%
  • 91-180 days 24%
  • 31-90 days 34%
  • 1-30 days 13%
Booked or blocked days in numbers
Days a year Winchester listings are booked or blocked
Days a yearShare of listingsListings
271-366 days2.6%1
181-270 days26.3%10
91-180 days23.7%9
31-90 days34.2%13
1-30 days13.2%5

What Is the Average Length of Stay for Airbnb in Winchester?

The average Winchester booking lasts 4.6 nights, longest in January and shortest in May. Listings took about 23 bookings each over the year. About two-thirds of listings that give a check-in time set it at 3 p.m., with check-out usually at 11 a.m.

Average length of stay by month in Winchester

Average nights per booking, by month of stay

Two-year average by calendar month.

Winchester Airbnb Minimum Stay Requirements

95% of listings in Winchester accept stays of one or two nights.

Minimum stay set by Winchester listings

Share of listings by the shortest stay they accept, from one night to 30 or more

  • 1 Night 58% 22 listings
  • 2 Nights 37% 14 listings
  • 3 Nights 3% 1 listing
  • 4-6 Nights 3% 1 listing

What Cancellation Policies Do Airbnb Hosts Use in Winchester?

Flexible is the most common cancellation policy in Winchester, used by 34% of listings; it refunds guests in full if they cancel at least a day before check-in. Hosts here lean flexible: more than six in ten listings offer Flexible or Moderate terms, against 32% on Firm or stricter ones.

Cancellation policies of Winchester listings, from most to least flexible

Share of listings by the policy they use

  • Flexible 34% 13 listings
  • Moderate 29% 11 listings
  • Limited 5% 2 listings
  • Firm 29% 11 listings
  • Strict 3% 1 listing

How Much Are Airbnb Cleaning Fees in Winchester?

84% of Winchester listings charge a cleaning fee. The typical fee is about $63. Spread over the average stay of 4.6 nights, that adds roughly $14 a night to what guests pay. For listings that charge one, cleaning fees make up about 10% of gross revenue.

Median cleaning fee
$63
Average cleaning fee
$79
Listings charging a fee
84.2%
Share of gross revenue
9.9%

Top earners

Top-Earning Airbnbs and Hosts in Winchester

The top-grossing Airbnb in Winchester, a four-bedroom home, took in $56,100 over the past year, about 3.5 times the city's average of $16,200. Three of the six listings below have two bedrooms or fewer, so size alone doesn't explain the top of this market.

Family Farm Winchester/Lexington 20 min.*Game Room Family Farm Winchester/Lexington 20 min.*Game Room Entire home · 4 bedrooms Rated 4.97
Revenue
$56,054
Occupancy
55.7%
Daily rate
$289
River Relaxation | Riverfront Home| Winchester River Relaxation | Riverfront Home| Winchester Entire home · 3 bedrooms Rated 4.73
Revenue
$50,033
Occupancy
57.0%
Daily rate
$208
Life is Better On The River Life is Better On The River Entire home · 2 bedrooms Rated 4.89
Revenue
$47,743
Occupancy
51.7%
Daily rate
$230
LenMar Farm Country Stay near Lexington KY LenMar Farm Country Stay near Lexington KY Entire home · 2 bedrooms Rated 4.94
Revenue
$29,231
Occupancy
72.3%
Daily rate
$109
College Park Getaway College Park Getaway Entire home · 3 bedrooms Rated 4.81
Revenue
$27,135
Occupancy
58.4%
Daily rate
$211
Riverview 2 … enjoy the view ! Riverview 2 … enjoy the view ! Entire home · 1 bedroom Rated 4.89
Revenue
$26,928
Occupancy
59.9%
Daily rate
$118

Who Are the Airbnb Hosts in Winchester?

Only 5% of Winchester listings are classed as professionally managed, though 45% of listings have a co-host. Six in ten listings are run by Superhosts, so a strong review record is the norm here rather than an edge. Most hosts still vet their guests: only 24% of listings accept Instant Book. Airbnb's Simplified Pricing, where the host pays the whole service fee and guests see one price with no separate Airbnb charge, covers 84% of listings.

Superhosts
60.5%
Professional management
5.3%
Cohosted listings
44.7%
Instant Book enabled
23.7%
Simplified Pricing
84.2%

Nearby markets

Winchester vs. Nearby Airbnb Markets

Of the eight nearby markets in the table, all within 48 km, Versailles (48 km away, 68 listings) earned the most per listing, about 2.6 times as much as Winchester. Georgetown was the busiest, booked on 46% of nights against 40% in Winchester.

Airbnb markets near Winchester: distance, revenue, nightly rate and occupancy
MarketListingsAvg. annual revenueAvg. nightly rateOccupancy
Paris 26 km36$21,970$23634%
Richmond 26 km58$21,812$16739%
Lexington 28 km819$31,959$24844%
Stanton 41 km322$28,379$22638%
Georgetown 42 km142$37,341$24746%
Berea 44 km71$14,535$14036%
Slade 48 km55$30,898$21941%
Versailles 48 km68$42,073$35144%

Other Airbnb Markets in Kentucky

See all 112 Kentucky Airbnb markets

Markets Similar to Winchester

Markets elsewhere in the United States with a similar nightly rate and occupancy to Winchester:

FAQ

Winchester Airbnb FAQ

How much do Airbnb hosts make in Winchester?

An active Winchester Airbnb grossed $16,186 on average in the 12 months to September 2026, according to AirROI's tracking of 38 active listings. That is before cleaning, management, taxes and financing. Busier, better-run listings do far better: the top quarter took in $2,530 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 $698 and $2,530 in a typical month, and the top tenth $3,800 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 40% of available nights over the past year. That compares with 39% for the Kentucky average. October is usually the busiest month.

How much does an Airbnb cost per night in Winchester?

The average booked night in Winchester cost $137 before fees. Half of listings charge between $81 and $185, so bedroom count and location move the price more than the average suggests.

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 $16,186 in the 12 months to September 2026, 42% below the Kentucky average of $27,730. Run by its owner, with the cleaning fee covering the cleaner and everyday costs for Airbnb's fee, utilities, supplies, upkeep and insurance, $10,536 a year (about $880 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 $1,440 a month. Check a specific home in the Airbnb estimator.

When is Airbnb peak season in Winchester?

October usually pays best, averaging $2,210 per active listing over the past two years, and January usually pays least. The month-by-month table above shows how the latest 12 months played out.

What is the Airbnb RevPAR in Winchester?

Each night a Winchester listing was open to book earned $57 on average over the past year, booked or not. That figure, revenue per available night (RevPAR), folds price and occupancy into one number; the top 10% of listings made $128 or more.

How far in advance do guests book Airbnbs in Winchester?

Winchester stays were booked 39 days (about six weeks) before arrival on average over the past year, so most of a month is booked well before it starts.

How long do guests stay at Airbnbs in Winchester?

The average Winchester Airbnb stay lasted 4.6 nights over the past year. A listing took 23 reservations over the year on average.

How are Airbnbs in Winchester rated?

Guests rate Winchester Airbnbs 4.81 out of 5 on average. Guests score communication highest and cleanliness lowest.

What are the best neighborhoods for Airbnb in Winchester?

Historic Downtown, Cedar Creek Lake and Buffalo Trace Distillery 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 38 active Airbnb listings in Winchester as of September 2026. The closest tracked market is Paris, 26 km away.

How much are Airbnb cleaning fees in Winchester?

In Winchester, 84% of listings add a cleaning fee, and the typical fee is about $63.

Method

About This Data

Figures on this page cover 38 active Airbnb listings in Winchester from October 2025 to September 2026 (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.