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Resorts in Windsor

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (528)
"Relaxing "
The price is SAR 1,684
SAR 2,018 total
includes taxes & fees
17 Aug - 18 Aug
Woodstock Inn & Resort

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (722)
"Excellent property large spacious rooms great restaurant on property"
The price is SAR 474
SAR 567 total
includes taxes & fees
6 Aug - 7 Aug
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Mountain Edge Suites at Sunapee, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (344)
"Always a great time here!"
The price is SAR 571
SAR 680 total
includes taxes & fees
24 Aug - 25 Aug
Mountain Edge Suites at Sunapee, Ascend Hotel Collection

Beautiful resort in the heart of Mount Sunapee steps from the mountain.

10.0 out of 10, Exceptional, (1)
"Overall fantastic experience!! Quick communication & extremely friendly staff. Pictures / posting of resort were a bit misleading. Much nicer than what was posted!! All amenities of Ascend hotel were included. "
Beautiful resort in the heart of Mount Sunapee steps from the mountain.

Mount Ascutney Resort in Beautiful Brownsville Vermont Amazing 1 Bedroom

Mount Ascutney Resort in Beautiful Brownsville Vermont Amazing 1 Bedroom

On The Mountain - 1 - Bedroom - Sleeps 6

On The Mountain - 1 - Bedroom - Sleeps 6

Mount Ascutney in Brownsville Vermont, A Beautiful Holiday Inn Club Resort

Mount Ascutney in Brownsville Vermont, A Beautiful Holiday Inn Club Resort

Mount Ascutney 1 Bedroom in Brownsville Vermont an IHG Holiday Inn Club Resort

Mount Ascutney 1 Bedroom in Brownsville Vermont an IHG Holiday Inn Club Resort

Mount Ascutney Beautiful 1 Bedroom Resort In Brownsville Vermont an IHG Vacation

Mount Ascutney Beautiful 1 Bedroom Resort In Brownsville Vermont an IHG Vacation
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.
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Top Windsor Hotel Reviews

Frequently asked questions

What can I expect from a resort vacation in Windsor?
Longing for a relaxing escape? Indulge in the comforts of a resort, where you can find everything you need for your stay from tasty food and drink options to entertainment and shopping. Browse the resorts in the area and discover the best one for you, whether you envision yourself kicking back in a suite with stunning views or checking out the on-site boutiques.
What's the best resort for my stay in Windsor?
Here are our top-rated resorts around Windsor: Woodstock Inn & Resort - Luxury resort. 11.9 mi (19.2 km) from Windsor. Features 4 restaurants, 2 bars, and a golf course. Holiday Inn Club Vacations Mount Ascutney Resort by IHG - 4.3 mi (7 km) from Windsor. Has a seasonal outdoor pool, a bar, and an indoor pool. Mountain Edge Suites at Sunapee, Ascend Hotel Collection - 18.8 mi (30.3 km) from Windsor. Enjoy the 2 indoor pools, free pool cabanas, and fitness center. Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA - 22.6 mi (36.3 km) from Windsor. Amenities include a hot tub. Beautiful resort in the heart of Mount Sunapee steps from the mountain. - 18.9 mi (30.5 km) from Windsor. Access to a fitness center.
What can I do in Windsor?
Harpoon Brewery, Mt Ascutney State Park, and Connecticut River are a few of the interesting sights to visit. A few other attractions you may want to see are American Precision Museum and Windsor Public Library.
What's the seasonal weather like in Windsor?
The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.
What's the best way to get to and around Windsor?
Fly into Lebanon, NH (LEB-Lebanon Municipal), which is located 10.7 mi (17.3 km) away from the city center. Otherwise, look for flights into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away. If you want to explore the larger area, hop aboard a train at Windsor Station.