Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

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

Fat Sheep Farm & Cabins
Aerial view

Fat Sheep Farm & Cabins

3.0 star property
9.6 out of 10, Exceptional, (9)
"Honestly as soon as I got there I knew I had made a good choice. Then I stepped into the cabin and knew I had made an excellent choice. It’s by far the cleanest place Ive stayed. I went looking for peace and quiet and I got just that. It’s silent, it’s beautiful, it’s private. Even though it’s deep winter I still got to hang in the barn, feed the animals, go on quiet hikes. The animals are extremely friendly, they’re are used to people and enjoy being petted. There’s this super nice lady who...
The price is AED 584
AED 817 total
includes taxes & fees
9 Feb - 10 Feb
Fat Sheep Farm & Cabins
Snapdragon Inn
Front of property

Snapdragon Inn

3.5 star property
9.6 out of 10, Exceptional, (17)
"The history of the house is provided. Beutiful house and grounds."
Snapdragon Inn
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

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Exterior

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (64)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is AED 514
AED 1,119 total
includes taxes & fees
24 Feb - 25 Feb
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
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 Studio at Okemo on Sachem Trail
Exterior

Ski In/Out Studio at Okemo on Sachem Trail

9.6 out of 10, Exceptional, (10)
"David was a great host. Place was as described, clean, conveniently located on Okemo mountain, walk right up to sachem trail, stay towards the left at the bottom and the quad bubble lift is right there."
Ski In/Out Studio at Okemo on Sachem Trail
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 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 spa 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 Mt Ascutney State Park and Connecticut River.
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.