Find Vacation Rentals in Winchester, Virginia

We have 508 properties to choose from
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

House Winchester
from $144 per night
House ∙ 4 guests ∙ 2 bedrooms

74 m² House

5.0
Outstanding(69 ratings)
Winchester, Virginia, United States
Vrbo
Details
House Winchester
from $185 per night
House ∙ 6 guests ∙ 2 bedrooms

2000 m² House

4.6
Excellent(9 ratings)
Winchester, Virginia, United States
Vrbo
Details
House Winchester
from $114 per night
House ∙ 6 guests ∙ 3 bedrooms

149 m² House

5.0
Outstanding(43 ratings)
Winchester, Virginia, United States
Vrbo
Details
House Winchester
from $311 per night
4 guests ∙ 2 bedrooms

House

4.4
Very good(3 ratings)
Winchester, Virginia, United States
Vrbo
Details
Apartment Winchester
from $112 per night
Apartment ∙ 3 guests ∙ 3 bedrooms

93 m² Apartment

5.0
Outstanding(2 ratings)
Winchester, Virginia, United States
Vrbo
Details
House Winchester
from $421 per night
11 guests ∙ 6 bedrooms

House

4.0
Very good(1 rating)
Winchester, Virginia, United States
Vrbo
Details
Apartment Winchester
from $138 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

116 m² Apartment

4.0
Very good(2 ratings)
Winchester, Virginia, United States
Vrbo
Details
House Winchester
from $379 per night
6 guests ∙ 3 bedrooms

House

Winchester, Virginia, United States
Vrbo
Details
Apartment Winchester
from $132 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

116 m² Apartment

5.0
Outstanding(1 rating)
Winchester, Virginia, United States
Vrbo
Details
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Recommended Rentals With Pools

Motel  Winchester
from $71 per night
Motel ∙ 2 guests ∙ 1 bedroom

26 m² Motel

4.0
Very good(1016 ratings)
Winchester, Virginia, United States
Pool
HomeToGo
Details
Motel  Winchester
from $70 per night
2 guests ∙ 1 bedroom

Motel

4.0
Very good(1016 ratings)
Winchester, Virginia, United States
Pool
HomeToGo
Details
Motel  Winchester
from $77 per night
Motel ∙ 4 guests ∙ 1 bedroom

26 m² Motel

4.0
Very good(1016 ratings)
Winchester, Virginia, United States
Pool
HomeToGo
Details
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Vacation rentals with Wi-Fi

Apartment  Winchester
from $175 per night
2 guests ∙ 1 bedroom

Apartment

5.0
Outstanding(4 ratings)
Winchester, Virginia, United States
Internet
Vrbo
Details
Apartment  Winchester
from $74 per night
2 guests ∙ 1 bedroom

Apartment

3.0
(1 rating)
Winchester, Virginia, United States
Internet
Vrbo
Details
Apartment  Winchester
from $196 per night
2 guests ∙ 1 bedroom

Apartment

4.0
Very good(4 ratings)
Winchester, Virginia, United States
Internet
Vrbo
Details
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Apartments and vacation rentals with a kitchen

Apartment  Winchester
from $143 per night
2 guests ∙ 1 bedroom

Apartment

3.0
(1 rating)
Winchester, Virginia, United States
Kitchen
Vrbo
Details
Apartment  Winchester
from $112 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

93 m² Apartment

5.0
Outstanding(1 rating)
Winchester, Virginia, United States
Kitchen
Vrbo
Details
House  Winchester
from $154 per night
House ∙ 6 guests ∙ 3 bedrooms

149 m² House

Winchester, Virginia, United States
Kitchen
Vio.com
Details
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Frequently Asked Questions

How much does it cost to stay in Winchester?

Prices for a stay in Winchester begin at $71 per night.

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

On tripping.com, you will find 508 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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