Winchester vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these vacation rentals 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 vacation rentals
Other great vacation rentals in Winchester
Loft in Purcellville
4.99 out of 5 average rating, 293 reviews"When Pigs Fly" Airbnb Most Hospitable Host in VA
Farm stay in Round Hill
4.94 out of 5 average rating, 351 reviewsCome and get your goat on!
Home in Edinburg
4.98 out of 5 average rating, 362 reviewsJay Birds Nest - Pet Friendly
Cottage in Shepherdstown
4.96 out of 5 average rating, 186 reviewsThe GW Hollida Cottage of Shepherdstown
Guesthouse in Round Hill
4.98 out of 5 average rating, 378 reviewsPrivate Carriage House
Cabin in Augusta ( Capon Bridge)
4.96 out of 5 average rating, 131 reviewsNirvana, Mountain View
Cabin in Lost City
4.96 out of 5 average rating, 253 reviewsHigh View Hideaway - A Cozy Lost River Cabin
Guest suite in Summit Point
4.97 out of 5 average rating, 132 reviewsThe Big Room - Historic Schoolhouse
Other great vacation rentals in Winchester
Cabin in Lost River
4.96 out of 5 average rating, 112 reviewsRustic and stylish mountain getaway
Apartment in Winchester
4.94 out of 5 average rating, 52 reviewsNewly repurposed Historic Home in Winchester VA!
Apartment in Winchester
5.0 out of 5 average rating, 12 reviewsCameron Corner: King Bed & Office Downtown
Apartment in Winchester
4.97 out of 5 average rating, 77 reviewsHistoric Wisteria House on Old Town Walking Mall
Place to stay in Winchester
4.88 out of 5 average rating, 51 reviewsCrash Landing
Home in Winchester
4.92 out of 5 average rating, 26 reviewsMisty Meadow has quite setting in the country.
Home in Winchester
4.92 out of 5 average rating, 12 reviewsCabin in Historic Old Town Winchester
Condo in Winchester
4.98 out of 5 average rating, 52 reviewsHistoric District Downtown Winchester
Quick stats about vacation rentals in Winchester
Total rentals
90 properties
Wifi availability
90 properties include access to wifi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
6K reviews
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 50 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winchester?
Four-legged friends are welcome in Winchester. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Winchester?
Experience the best of Winchester with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Winchester have wifi?
Absolutely! We offer over 30 house rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winchester have self check-in?
Absolutely! We offer over 20 apartment rentals with self check-in in Winchester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Winchester?
Winchester has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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