288 Winchester Vacation Rentals & Short Term Rentals

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Compare Winchester vacation rentals from 6 rental sites including Booking.com, HomeAway, HRS Holidays and more, ranging from $25 to $1670 a night.

Information about Winchester

Vacation Rentals in Winchester

Looking for a vacation rental in Winchester? Tripping.com has 288 rental homes available in Winchester. Potential renters will find 2 studios, 199 1-bedroom, 40 2-bedroom and 47 rentals with 3 or more bedrooms ranging from $25 a night to $1670 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Winchester is $217 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, 179 rentals have internet and wifi, 120 have TV and/or cable and 96 have a pool or hot tub.

Search properties from 6 rental sites in Winchester where the top providers in that area are Booking.com, HomeAway, and HRS Holidays. There are 86 Booking.com rentals, 80 HomeAway short term rentals and 63 HRS Holidays vacation rentals.