Vacation Homes in Windsor
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Vacation Homes in Windsor

Beautifully renovated with fireplace and coffee bar

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Charming Lakefront Cottage on Lake Mascoma

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Lakefront Family Home w/ Dock in Newport!

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Top trending hotels in Windsor

Fat Sheep Farm & Cabins
Vacation Rentals in Windsor
What kind of vacation do you want in Windsor? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Windsor that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Windsor, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Windsor Vacation Homes essential information
Accommodation | 856 Vacation Homes |
---|---|
Lowest Price | CA $149 |
Highest Price | CA $428 |
Popular accommodation | Beautifully renovated with fireplace and coffee bar, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee, Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont, Charming Lakefront Cottage on Lake Mascoma, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table, ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace, Lakefront Family Home w/ Dock in Newport!, Dog-friendly house with picturesque mountain view & near skiing - close to Okemo, Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing |