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Featured Vacation Homes in Windsor

Attention Cottagers .birders, Beach Goers and Boaters Come Check This Cottage .
Attention Cottagers .birders, Beach Goers and Boaters Come Check This Cottage .
Leamington, ON
At this vacation home, guests have access to barbecue grills.
Hall House: Entire House for Your Stay
Hall House: Entire House for Your Stay
Windsor, ON
This vacation home is a smoke-free vacation home.
NEW Luxury, Willow Beach Cottage Steps to the Lake
NEW Luxury, Willow Beach Cottage Steps to the Lake
Amherstburg, ON
Guests staying at this vacation home enjoy a water park, a garden, and barbecue grills.
Beautiful 3 BR Ranch House Waterfront on Lake Erie
Beautiful 3 BR Ranch House Waterfront on Lake Erie
Chatham-Kent, ON
At this vacation home, guests have access to a garden.
Oasis At The Point B&B - Lotus Room
Oasis At The Point B&B - Lotus Room
Leamington, ON
At this vacation home, guests have access to a garden.
Anchors Away
Anchors Away
3.5 out of 5.0 273 Robson Rd., Leamington, ON
At this vacation home, guests have access to free WiFi in public areas, express check-in, and express check-out. If you plan to drive, free parking is available. ...
Oasis At The Point B&B - Forest Room
Oasis At The Point B&B - Forest Room
Leamington, ON
This vacation home is a smoke-free vacation home.
4 BR Executive Town Home, Indoor Pool, Close to Shopping, Restaurants, and Parks
4 BR Executive Town Home, Indoor Pool, Close to Shopping, Restaurants, and Parks
Windsor, ON
Guests staying at this vacation home enjoy features like an indoor pool.
8 Bedroom Gem on the River
8 Bedroom Gem on the River
Amherstburg, ON
At this vacation home, guests have access to features like an arcade/game room. This historic vacation home also has a garden.
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Windsor Vacation Homes

Book vacation homes in Windsor
Next time you take a group getaway top Windsor, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Windsor vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Windsor vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Windsor; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Windsor rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Windsor is sure to be a winner.

Hotel Options in Windsor

See all 123 Properties in Windsor
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.