108 Winchester Vacation Rentals & Short Term Rentals

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Compare Winchester vacation rentals from 8 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $25 to $3058 a night.

Information about Winchester

Vacation Rentals in Winchester

Find the best Winchester vacation rentals with Tripping.com. Choose from 321 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $3058 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 252 of homes in Winchester offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 28 rentals with pool or jacuzzi, or relax with the family in one of the 163 homes with cable TV.

For all those dog lovers and cat lovers, Winchester offers 110 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 8 rental sites in Winchester where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 104 HomeAway rentals, 87 Booking.com short term rentals and 64 TripAdvisor vacation rentals.