127 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 10 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $25 to $1061 a night.

Information about Winchester

Vacation Rentals in Winchester

Find the best Winchester vacation rentals with Tripping.com. Choose from 329 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 $1061 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 246 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 30 rentals with pool or jacuzzi, or relax with the family in one of the 153 homes with cable TV.

For all those dog lovers and cat lovers, Winchester offers 115 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 10 rental sites in Winchester where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 109 HomeAway rentals, 81 Booking.com short term rentals and 57 TripAdvisor vacation rentals.