Windsor Vacation Rentals
Check Windsor vacation rental availability
Vacation Rentals in Windsor
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Treehouse at Wise Pines- SoBo
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Idyllic Lakefront House Suited Two Families
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Beautifully renovated with fireplace and coffee bar
Killington Center Inn & Suites by Killington VR - Studios
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Lakefront home with amazing views, fireplace, firepit, & gas grill
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
Lake Sunapee Gathering Place, Serene Restored Barn
Windsor Vacation Rental Travel Info
Popular accommodation | Windsor private vacation homes |
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Known landmarks | Mt Ascutney State Park, Harpoon Brewery and American Precision Museum |
International airports | Lebanon, NH (LEB-Lebanon Municipal) and Rutland, VT (RUT-Rutland Southern Vermont Regional) |
Other types of properties in Windsor you may be interested in
Killington Mountain Lodge, Tapestry Collection by Hilton
Hotel Coolidge
Woodstock Inn & Resort
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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