0 Bedrooms for 1 Guest
Price $10 - $1000+

421 Winchester Vacation Rentals & Short Term 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 vacation rentals from 7 rental sites including Booking.com, HomeAway, TripAdvisor, and more, ranging from $26 to $1253 a night. 

    Information about Winchester

    Vacation Rentals in Winchester

    Find the best Winchester vacation rentals with Tripping.com. Choose from 421 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 $26 a night to $1253 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 123 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 11 rentals with pool or jacuzzi, or relax with the family in one of the 364 homes with cable TV.

    For all those dog lovers and cat lovers, Winchester offers 43 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 7 rental sites in Winchester where the top providers in that area are Booking.com, HomeAway, and TripAdvisor. There are 256 Booking.com rentals, 66 HomeAway short term rentals and 59 TripAdvisor vacation rentals.