Guests
2
Bedrooms
0+
Bathrooms
0+
Availability
Instantly Bookable
Nightly Budget
$10 - $1,000+
Rate
Nightly
Weekly
Monthly
Amenities
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Pets
Internet
Pool
Parking
HOME TYPE
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House
Apartment
Hotel Room
Cabin
Keywords
Ex: Beach, Downtown, Lake...

105 Winchester Holiday Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Winchester holiday rentals from 6 rental sites including TripAdvisor, HomeAway, Booking.com and more, from $52 a night.

Winchester Information

Vacation Rentals in Winchester

Looking for a vacation rental in Winchester? Tripping.com has 96 vacation rental homes available in Winchester. You'll find 0 studios, 47 1-bedroom, 30 2-bedroom and 19 rentals with 3 or more bedrooms ranging from $52 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Winchester is $256 while the average price of a weekly rental is $694. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Winchester home is $25.

Wondering if you can bring your dog or cat along with you? There are 30 pet-friendly vacation rentals available in Winchester. In addition to accommodating pets, Winchester rentals offer a variety of amenities. In particular, 79 rentals have Internet and WiFi, 60 have TV and/or cable and 3 have a pool or hot tub.

Search properties from 6 vacation rental sites in Winchester where the top providers in that area are TripAdvisor, HomeAway, and Booking.com. There are 37 TripAdvisor rentals, 28 HomeAway short term rentals and 21 Booking.com vacation rentals.