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
Cottage in Strasburg
The Cottage at the Barb Farm
Cabin in Lost City
High View Hideaway - A Cozy Lost River Cabin
Guesthouse in Round Hill
Private Carriage House
Cabin in Augusta ( Capon Bridge)
Nirvana, Mountain View
Home in Edinburg
Charming, Parkview Cottage, King bed, 1 mi to I-81
Home in Inwood
Arden House, Inwood WV
Home in Edinburg
Jay Birds Nest - Pet Friendly
Cabin in Gerrardstown
Cabin in the Treetops with Views and Nearby Creek
Other great vacation rentals in Winchester
Condo in Winchester
Historic District Downtown Winchester
Home in Winchester
Whole 3-bedroom house walkable to downtown.
Home in Winchester
Misty Meadow has quite setting in the country.
Guest suite in Clear Brook
Bluebird Bungalow
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
Rental unit in Winchester
Home Away from Home
Guest suite in Stephens City
Cozy Cabin
Guest suite in Winchester
Retro Vibe Studio
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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