Find Vacation Rentals in Winchester, Virginia

We have 496 properties to choose from
Winchester
Anytime
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Winchester
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

House Winchester
$150 per night
House ∙ 6 guests ∙ 3 bedrooms
Winchester, Virginia, United States
Details
Vrbo
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House Winchester
$149 per night
House ∙ 6 guests ∙ 3 bedrooms
Winchester, Virginia, United States
Details
Vrbo
Details
Details
Apartment Winchester
$63 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Winchester, Virginia, United States
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Vrbo
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Motel Winchester
$70 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.1
(499 ratings)
Winchester, Virginia, United States
Details
HomeToGo
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House Winchester
$179 per night
House ∙ 6 guests ∙ 3 bedrooms
Winchester, Virginia, United States
Details
Vrbo
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House Winchester
$148 per night
House ∙ 6 guests ∙ 2 bedrooms
4.4
Very good (3 ratings)
Winchester, Virginia, United States
Details
Vrbo
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House Winchester
$134 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (73 ratings)
Winchester, Virginia, United States
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Vrbo
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House Winchester
$115 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (43 ratings)
Winchester, Virginia, United States
Details
Vrbo
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Condo Winchester
$232 per night
Condo ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Winchester, Virginia, United States
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Vrbo
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Recommended Rentals With Pools

Motel  Winchester
$71 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.8
Good (970 ratings)
Winchester, Virginia, United States
Pool
Details
HomeToGo
Details
Details
Motel  Winchester
$78 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.8
Good (970 ratings)
Winchester, Virginia, United States
Pool
Details
HomeToGo
Details
Details
Motel  Winchester
$71 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.8
Good (970 ratings)
Winchester, Virginia, United States
Pool
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HomeToGo
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Pet-Friendly Homes and Apartments

Apartment  Winchester
$60 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Winchester, Virginia, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Winchester
$85 per night
Apartment ∙ 2 guests ∙ 2 bedrooms
Winchester, Virginia, United States
Pet-friendly
Details
Vrbo
Details
Details
Motel  Winchester
$72 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.7
Good (59 ratings)
Winchester, Virginia, United States
Pet-friendly
Details
HomeToGo
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Vacation rentals and apartments with air conditioning

Motel  Winchester
$70 per night
Motel ∙ 3 guests ∙ 1 bedroom
3.1
(499 ratings)
Winchester, Virginia, United States
Air conditioning
Details
HomeToGo
Details
Details
Motel  Winchester
$62 per night
Motel ∙ 2 guests ∙ 1 bedroom
3.1
(499 ratings)
Winchester, Virginia, United States
Air conditioning
Details
HomeToGo
Details
Details
Motel  Winchester
$70 per night
Motel ∙ 4 guests ∙ 1 bedroom
3.1
(499 ratings)
Winchester, Virginia, United States
Air conditioning
Details
HomeToGo
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Frequently Asked Questions

How much does it cost to stay in Winchester?

Prices for a stay in Winchester begin at $64 per night.

Are there lots vacation rental options to choose from in Winchester?

On tripping.com, you will find 496 available vacation rental offers in Winchester.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winchester

Find the best Winchester vacation rentals on Tripping.com. With over 73 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Winchester range from $43 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 46 homes in Winchester offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 37 rentals with pool or jacuzzi, or relax with the family in one of the 48 homes with cable TV. For all those pet owners with dogs or cats, Winchester offers 17 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 5 vacation rental sites in Winchester where the top providers in that area are HRS Holidays, Booking.com, and Agoda. There are 28 HRS Holidays rentals, 16 Booking.com short term rentals and 11 Agoda vacation rentals.

Popular Day Trips Near Winchester

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