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

29 Winchester Holiday Rentals, Houses & Apartments

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 3 rental sites including Booking.com, HRS Holidays, HomeAway, and more, ranging from $42 to $1500 a night. 
Showing 29 personalized results

    Information about Winchester

    Vacation Rentals in Winchester

    Find the best Winchester vacation rentals with Tripping.com. Choose from 25 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 $42 a night to $1500 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 3 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 2 rentals with pool or jacuzzi, or relax with the family in one of the 20 homes with cable TV.

    For all those dog lovers and cat lovers, Winchester offers 1 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 3 rental sites in Winchester where the top providers in that area are Booking.com, HRS Holidays, and HomeAway. There are 20 Booking.com rentals, 4 HRS Holidays short term rentals and 1 HomeAway vacation rentals.