Windsor Vacation Homes

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Featured Vacation Homes in Windsor

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Windsor

    Fat Sheep Farm & Cabins

    Fat Sheep Farm & Cabins

    122 Best Rd Windsor VT
    $168 nightly
    The price is $183 total per night from Nov 22 to Nov 23
    $183 total
    Nov 22 - Nov 23
    Total with taxes and fees
    9.8/10 Exceptional! (15 reviews)
    Fireside Inn & Suites West Lebanon

    Fireside Inn & Suites West Lebanon

    25 Airport Road West Lebanon NH
    $128 nightly
    The price is $139 total per night from Nov 9 to Nov 10
    $139 total
    Nov 9 - Nov 10
    Total with taxes and fees
    The Mountain Inn at Killington

    The Mountain Inn at Killington

    47 Old Mill Rd Killington VT
    $156 nightly
    The price is $172 total per night from Dec 8 to Dec 9
    $172 total
    Dec 8 - Dec 9
    Total with taxes and fees

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.

Windsor Vacation Homes essential information

Accommodation
782 Vacation Homes
Lowest Price
$139
Highest Price
$569
Popular accommodation
New Ludlow Village Home with Stunning Okemo Mountain View, Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock, ☆ SKI ON/OFF! ☆ 2BR+ Trailside! Hot tub, pool, gym +more, Killington, Vermont Ski House w/ Hot Tub and Sauna, The Dorothy-10 minutes from Okemo- freshly renovated, Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12, Historic Farmhouse on Working VT Farm & Hot Tub, Fabulous 4-bedroom house in Ludlow perfect for your ski getaway, Ultimate On-Mountain Ski House! Private 3 Bedroom + Loft, 200' from Trail, Sauna