Photo by William E Berry Jr.

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Compare 7 Resorts in Windsor with updated reviews, rates, and availability.

Woodstock Inn & Resort
Exterior

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (491)
"The room was very small yet comfortable. Bathroom was very tight. Very little space to put things. The bed was very soft and cozy. However there was a dead bug squished in The curtains. Cookies and hot chocolate were a nice touch and a wine tasing with great cheese was a special treat. The entrance to the Billings farm was free because we stayed at the Inn. Nice touch."
The price is AED 1,135
AED 1,410 total
includes taxes & fees
20 Jan - 21 January 2025
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (651)
"Don't have elevator, and no hot breakfast provided "
The price is AED 547
AED 647 total
includes taxes & fees
20 Jan - 21 January 2025
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Mountain Edge Suites at Sunapee, Ascend Hotel Collection
Exterior

Mountain Edge Suites at Sunapee, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (301)
"Perfect "
The price is AED 768
AED 873 total
includes taxes & fees
6 Jan - 7 January 2025
Mountain Edge Suites at Sunapee, Ascend Hotel Collection
Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM
Exterior

Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM

Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM
Beautiful resort in the heart of Mount Sunapee steps from the mountain.
Dining

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

Beautiful resort in the heart of Mount Sunapee steps from the mountain.
On The Mountain - 1 - Bedroom - Sleeps 6
Exterior

On The Mountain - 1 - Bedroom - Sleeps 6

On The Mountain - 1 - Bedroom - Sleeps 6
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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Beautiful Myrtle Beach Condo with Amenities Galore

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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.

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, an IHG Hotel - 4.4 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 Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM - 22.6 mi (36.3 km) from Windsor. 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 South Congregational Church.
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.