283 Winchester Vacation Rentals & Short Term Rentals

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Compare Winchester vacation rentals from 6 rental sites including HomeAway, Booking.com, HRS Holidays and more, from $38 a night.

Information about Winchester

Vacation Rentals in Winchester

Looking for a vacation rental in Winchester? Tripping.com has 272 rental homes available in Winchester. Potential renters will find 2 studios, 190 1-bedroom, 33 2-bedroom and 47 rentals with 3 or more bedrooms from $38 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Winchester is $221 while the average price of a weekly rental is $620. 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 $2478.

Wondering if you can bring your favorite dog or cat with you? We have 69 pet friendly vacation rentals available for you. In addition to accommodating pets, Winchester rentals offer a variety of amenities. In particular, 175 rentals have internet and wifi, 115 have TV and/or cable and 89 have a pool or hot tub.

Search properties from 6 rental sites in Winchester where the top providers in that area are HomeAway, Booking.com, and HRS Holidays. There are 84 HomeAway rentals, 76 Booking.com short term rentals and 63 HRS Holidays vacation rentals.