
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
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Vacation rentals for every style
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Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester

Hidden in the Valley | Pool | Pets | Fire Pit

The Philosopher’s Retreat

Homestead with Shenandoah Valley Views

Ventura Cottage: 360-views/HotTub/4 acres/Gym

Easy like a Sunday Morning 1 BR apt great location

Pugh’s Paradise - Riverfront

Spacious Charming Basement Apt

Skyview Farmhouse
Quick stats about vacation rentals in Winchester
Total rentals
110 properties
Total number of reviews
7.5K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
110 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 70 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 40 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 40 house 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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