Vacation rentals with outdoor seating in Winchester
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Winchester
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Winchester outdoor seating rentals
House rentals with outdoor seating
Home in Franklin
4.95 out of 5 average rating, 131 reviewsPine Ridge Manor-Private Hot Tub, Secluded Hilltop
Aug. 18 – 25
Home in Woodstock
4.98 out of 5 average rating, 480 reviewsCaretaker Cottage at Burnshire Dam
Jan. 21 – 28
Home in Blue Ridge Summit
5.0 out of 5 average rating, 451 reviewsColonial Era Spring House
Oct. 14 – 21
Home in Edinburg
4.99 out of 5 average rating, 336 reviewsThe Burrow ~ Our guest reviews say it all!
Apr. 15 – 22
Home in Bluemont
4.93 out of 5 average rating, 203 reviewsThe Country French Cottage at High Meadows Estate
Feb. 1 – 8
Home in Myersville
4.97 out of 5 average rating, 148 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Oct. 8 – 15
Home in Berryville
4.95 out of 5 average rating, 190 reviewsRiverfront Getaway w/ Breathtaking Views!
Jul. 18 – 25
Home in Baker
4.95 out of 5 average rating, 290 reviewsLittle House on the Prairie in Baker WV
Jan. 5 – 12
Apartment rentals with outdoor seating
Apartment in Capon Bridge
4.99 out of 5 average rating, 114 reviewsPaw Paw Suite ~ 1 of 5 Unique Stays at Basswood
Jan. 2 – 9
Apartment in The Plains
4.98 out of 5 average rating, 451 reviewsRose End
Aug. 16 – 23
Apartment in Elkton
4.98 out of 5 average rating, 296 reviewsQuail Run - Country convenience and comfort!
Aug. 31 – Sep. 7
Apartment in Shepherdstown
4.97 out of 5 average rating, 156 reviewsDowntown Luxe Apt: Pet Friendly & Fenced Courtyard
Jun. 30 – Jul. 7
Apartment in Culpeper
4.98 out of 5 average rating, 148 reviewsTreeTop at Mt Run Lake (Private Guest Apartment)
Apr. 11 – 18
Apartment in Shepherdstown
4.98 out of 5 average rating, 117 reviewsThe 1763 House - Stay in Downtown Shepherdstown
Jun. 26 – Jul. 3
Apartment in Harpers Ferry
4.99 out of 5 average rating, 363 reviewsTaylor Den
Jun. 11 – 18
Apartment in Elkton
4.98 out of 5 average rating, 190 reviewsAwesome View
Jan. 27 – Feb. 3
Condo rentals with outdoor seating
Condo in Chambersburg
4.98 out of 5 average rating, 222 reviewsOne-bedroom apartment with separate entrance.
Apr. 7 – 14
Condo in Basye
4.92 out of 5 average rating, 110 reviewsFully Renovated 1-Br Condo at Bryce ~ Sleeps 4
Jan. 14 – 21
Condo in Occoquan
4.93 out of 5 average rating, 392 reviewsThe Daisy in Historic Occoquan (Mins to DC)
Nov. 13 – 20
Condo in Champion
4.98 out of 5 average rating, 125 reviewsCozy Laurel Highlands Getaway
Dec. 9 – 16
Condo in Davis
4.84 out of 5 average rating, 129 reviewsWalk to Dolly Sods, Mountain Views + Gas Fireplace
May 27 – Jun. 3
Condo in Dry Fork
4.86 out of 5 average rating, 144 reviewsTaylored Four All Seasons at Slopeside Condos
Sep. 29 – Oct. 6
Condo in McLean
4.82 out of 5 average rating, 126 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
Jul. 28 – Aug. 4
Condo in Martinsburg
4.98 out of 5 average rating, 57 reviewsThe Cozy Villa
Nov. 28 – Dec. 5
Quick stats about vacation rentals with outdoor seating in Winchester
Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$82 CAD before taxes and fees
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