Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 6 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, (501)
"Great resort, beautiful property-only issue was room was cold - aside from that, loved the stay "
The price is SAR 1,121
SAR 1,398 total
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort

3.0 star property
9.0 out of 10, Wonderful, (673)
"We loved this resort! We had our family of 6 in a 3 bedroom unit and it was so spacious. It was clean and very well maintained. Kids enjoyed the pool, game room and movie theatre! We would definitely recommend, especially for families!"
The price is SAR 446
SAR 538 total
includes taxes & fees
10 Mar - 11 Mar
Holiday Inn Club Vacations Mount Ascutney Resort
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, (316)
"Great customer service "
The price is SAR 671
SAR 769 total
includes taxes & fees
23 Mar - 24 Mar
Mountain Edge Suites at Sunapee, Ascend Hotel Collection
Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
Exterior

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
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)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.2 out of 10, Wonderful, (66)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is SAR 300
SAR 1,043 total
includes taxes & fees
24 Feb - 25 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

9.2 out of 10, Wonderful, (27)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
The price is SAR 248
SAR 715 total
includes taxes & fees
2 Mar - 3 Mar
Efficient condo near slopes with kitchenette & great 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 - 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?
Upper Valley Aquatic Center offers fun for the whole family, while Okemo Mountain Resort is one of the most popular places to visit nearby. A few other attractions you may want to see are American Precision Museum and Harpoon Brewery.
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.