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
Home in Sabillasville
4.93 out of 5 average rating, 109 reviewsStoney Spring Overlook
Cabin in Augusta ( Capon Bridge)
4.97 out of 5 average rating, 145 reviewsNirvana, Mountain View
Home in Winchester
5 out of 5 average rating, 20 reviewsGreat house 3 bedrooms, 3 beds
Cottage in Harpers Ferry
5 out of 5 average rating, 59 reviewsCozy Mountain Cottage Perfect for Friends & Family
Home in McGaheysville
4.78 out of 5 average rating, 27 reviewsSnowbird Lodge @ Massanutten Resort
Vacation home in Luray
4.83 out of 5 average rating, 121 reviews★ Cozy Country Cabin ★ near Luray & hiking trails!
Tiny home in Springfield
5 out of 5 average rating, 7 reviewsMt. View Escape (Dreammore) Deer Hunters Special
Home in McGaheysville
4.96 out of 5 average rating, 49 reviewsIn Resort- Family fun- Kids Suite-Game Room
Quick stats about vacation rentals in Winchester
Total rentals
100 properties
Total number of reviews
6.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 60 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 30 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.
What are the most popular amenities for Apartment Rentals in Winchester?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with wifi, over 20 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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