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, 294 reviews"When Pigs Fly" Airbnb Most Hospitable Host in VA
Cabin in Gerrardstown
4.88 out of 5 average rating, 186 reviewsModern Treetop Cabin with Views and Nearby Creek
Cottage in Strasburg
4.95 out of 5 average rating, 390 reviewsThe Cottage at the Barb Farm
Cabin in Lost City
4.96 out of 5 average rating, 254 reviewsHigh View Hideaway - A Cozy Lost River Cabin
Guest suite in Shepherdstown
4.95 out of 5 average rating, 572 reviewsHistoric Scrabble, Shepherdstown
Home in Inwood
4.89 out of 5 average rating, 558 reviewsArden House, Inwood WV
Guesthouse in Warrenton
4.98 out of 5 average rating, 259 reviewsThe Alton Cottage -a luxury country retreat
Guesthouse in Round Hill
4.98 out of 5 average rating, 380 reviewsPrivate Carriage House
Other great vacation rentals in Winchester
Guesthouse in Smithsburg
4.97 out of 5 average rating, 650 reviewsJewel Vinsota Artist's Guesthouse
Bungalow in Great Cacapon
4.9 out of 5 average rating, 471 reviewsRooster Wrest in the Trees
Cabin in Front Royal
4.98 out of 5 average rating, 110 reviewsThe Wizard's Chalet • Cozy nature escape • Hot Tub
Apartment in Winchester
4.97 out of 5 average rating, 79 reviewsHistoric Wisteria House on Old Town Walking Mall
Apartment in Winchester
4.93 out of 5 average rating, 54 reviewsNewly repurposed Historic Home in Winchester VA!
Home in Winchester
4.93 out of 5 average rating, 27 reviewsMisty Meadow has quite setting in the country.
Place to stay in Winchester
4.89 out of 5 average rating, 53 reviewsCrash Landing
Home in Winchester
4.92 out of 5 average rating, 13 reviewsCabin in Historic Old Town 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 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 house rentals in Winchester have self check-in?
Absolutely! We offer over 10 house 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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