Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
winchester va
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
National parks
Countryside
Cabins
Lake
Amazing views
Farms
Skiing
Amazing pools
Play
Rooms
Vineyards
Tiny homes
Trending
Chef's kitchens
Bed & breakfasts
Lakefront
Design
New
Camping
A-frames
Golfing
Ski-in/out
Barns
Treehouses
Off-the-grid
Yurts
Mansions
Grand pianos
Filters
, 1 filter applied
1
Show map
Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Learn how we sort results
Learn how we sort results
Guest favorite
Guest favorite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
2 beds
May 6 – 11
May 6 – 11
€ 139
night
€ 139 per night
·
€ 694 total
€ 694 total
Show price breakdown
4.95 out of 5 average rating, 164 reviews
4.95 (164)
Guest favorite
Guest favorite
Home in Winchester
Indigo Blue modern open vibe on tree lined street
Professional Host
Professional Host
Apr 1 – 6
Apr 1 – 6
€ 282
night
€ 282 per night
·
€ 1,408 total
€ 1,408 total
Show price breakdown
4.93 out of 5 average rating, 148 reviews
4.93 (148)
Guest favorite
Guest favorite
Apartment in Winchester
Newly repurposed Historic Home in Winchester VA!
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
€ 119
night
€ 119 per night
·
€ 593 total
€ 593 total
Show price breakdown
4.96 out of 5 average rating, 45 reviews
4.96 (45)
Guest favorite
Guest favorite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
€ 239
night
€ 239 per night
·
€ 1,194 total
€ 1,194 total
Show price breakdown
4.92 out of 5 average rating, 36 reviews
4.92 (36)
Guest favorite
Guest favorite
Apartment in Winchester
Downtown 1920's Gas Station
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
€ 148
night
€ 148 per night
·
€ 737 total
€ 737 total
Show price breakdown
4.94 out of 5 average rating, 264 reviews
4.94 (264)
Guest favorite
Guest favorite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Professional Host
Professional Host
Apr 5 – 10
Apr 5 – 10
€ 189
€ 168
night
€ 168 per night, originally € 189
·
€ 840 total
€ 840 total
Show price breakdown
5.0 out of 5 average rating, 134 reviews
5.0 (134)
Guest favorite
Guest favorite
Apartment in Winchester
Modern Twist in Old Town! Rock n' Roll FUN!
Individual Host
Individual Host
Apr 1 – 6
Apr 1 – 6
€ 157
night
€ 157 per night
·
€ 782 total
€ 782 total
Show price breakdown
4.89 out of 5 average rating, 101 reviews
4.89 (101)
Home in Winchester
Downtown Chic Condo w/parking
Individual Host
Individual Host
Apr 4 – 9
Apr 4 – 9
€ 146
night
€ 146 per night
·
€ 727 total
€ 727 total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Winchester
City Charmer minutes from Old Town
Individual Host
Individual Host
Apr 3 – 8
Apr 3 – 8
€ 145
night
€ 145 per night
·
€ 721 total
€ 721 total
Show price breakdown
4.97 out of 5 average rating, 210 reviews
4.97 (210)
Guest favorite
Guest favorite
Cottage in Winchester
Emma's Stone Cottage
Individual Host
Individual Host
Apr 7 – 12
Apr 7 – 12
€ 146
night
€ 146 per night
·
€ 726 total
€ 726 total
Show price breakdown
4.97 out of 5 average rating, 417 reviews
4.97 (417)
Home in Winchester
Historic District Charm On Cameron Street
Individual Host
Individual Host
Apr 1 – 6
Apr 1 – 6
€ 177
night
€ 177 per night
·
€ 884 total
€ 884 total
Show price breakdown
4.94 out of 5 average rating, 116 reviews
4.94 (116)
Guest favorite
Guest favorite
Cabin in High View
Mary's Cabin
4 beds
4 beds
May 6 – 11
May 6 – 11
€ 132
night
€ 132 per night
·
€ 658 total
€ 658 total
Show price breakdown
5.0 out of 5 average rating, 35 reviews
5.0 (35)
Guest favorite
Guest favorite
Apartment in Winchester
Downtowner
Individual Host
Individual Host
Apr 21 – 26
Apr 21 – 26
€ 153
night
€ 153 per night
·
€ 761 total
€ 761 total
Show price breakdown
4.98 out of 5 average rating, 214 reviews
4.98 (214)
Apartment in Winchester
Country in the Valley
Individual Host
Individual Host
Apr 5 – 10
Apr 5 – 10
€ 166
night
€ 166 per night
·
€ 828 total
€ 828 total
Show price breakdown
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
Professional Host
Professional Host
Apr 21 – 26
Apr 21 – 26
€ 235
night
€ 235 per night
·
€ 1,175 total
€ 1,175 total
Show price breakdown
4.97 out of 5 average rating, 163 reviews
4.97 (163)
Guest favorite
Guest favorite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Individual Host
Individual Host
Apr 2 – 7
Apr 2 – 7
€ 185
night
€ 185 per night
·
€ 924 total
€ 924 total
Show price breakdown
4.97 out of 5 average rating, 75 reviews
4.97 (75)
Guest favorite
Guest favorite
Cottage in Winchester
Uber SXY Private Country Escape! Hot Tub & Views~
Individual Host
Individual Host
May 29 – Jun 3
May 29 – Jun 3
€ 266
night
€ 266 per night
·
€ 1,326 total
€ 1,326 total
Show price breakdown
4.98 out of 5 average rating, 296 reviews
4.98 (296)
Guest favorite
Guest favorite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
€ 399
night
€ 399 per night
·
€ 1,992 total
€ 1,992 total
Show price breakdown
5.0 out of 5 average rating, 18 reviews
5.0 (18)
1
2
3
4
…
15