Winchester vacation rentals
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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, 298 reviews"When Pigs Fly" Airbnb Most Hospitable Host in VA
Tiny home in Linville
4.99 out of 5 average rating, 614 reviewsThe spring house at Thistle Hollow
Home in Edinburg
4.98 out of 5 average rating, 373 reviewsJay Birds Nest - Pet Friendly
Apartment in The Plains
4.98 out of 5 average rating, 464 reviewsRose End
Cottage in Shepherdstown
4.96 out of 5 average rating, 197 reviewsThe GW Hollida Cottage of Shepherdstown
Cabin in Lost City
4.96 out of 5 average rating, 256 reviewsHigh View Hideaway - A Cozy Lost River Cabin
Guesthouse in Round Hill
4.98 out of 5 average rating, 387 reviewsPrivate Carriage House
Home in Inwood
4.89 out of 5 average rating, 562 reviewsArden House, Inwood WV
Other great vacation rentals in Winchester
Home in Winchester
4.94 out of 5 average rating, 16 reviewsCabin in Historic Old Town Winchester
Condo in Winchester
4.98 out of 5 average rating, 54 reviewsHistoric District Downtown Winchester
Guest suite in Clear Brook
5.0 out of 5 average rating, 43 reviewsBluebird Bungalow
Guest suite in Stephens City
4.93 out of 5 average rating, 30 reviewsCozy Cabin
Townhouse in Winchester
4.91 out of 5 average rating, 45 reviewsBrewhouse renovated row house steps from downtown
Home in Winchester
4.93 out of 5 average rating, 28 reviewsMisty Meadow has quite setting in the country.
Barn in Berryville
4.81 out of 5 average rating, 93 reviewsModern House Barn on 66 acre Horse Farm
Home in Winchester
5.0 out of 5 average rating, 29 reviewsWhole 3-bedroom house walkable to downtown.
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 apartment rentals in Winchester have wifi?
Absolutely! We offer over 30 apartment 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 house rentals in Winchester?
Winchester has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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