50 Windsor Holiday Rentals

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Compare Windsor holiday rentals from 7 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $63 to $11071 a night.

Information about Windsor

Vacation Rentals in Windsor

Find the best Windsor vacation rentals with Tripping.com. Choose from 509 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 $63 a night to $11071 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 437 of homes in Windsor offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 133 rentals with pool or jacuzzi, or relax with the family in one of the 367 homes with cable TV.

For all those dog lovers and cat lovers, Windsor offers 151 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 Windsor where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 304 HomeAway rentals, 74 TripAdvisor short term rentals and 72 Booking.com vacation rentals.