Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Windsor Resorts

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (500)
"Great trip! "
The price is CA $431
CA $537 total
includes taxes & fees
Mar 2 - Mar 3
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, (665)
"Our large family with kids stayed here for ski vacation. Comfortable beds , clean rooms. Kitchen fully stuffed with necessary kitchen items. 40 minutes drive from Killington. Kids enjoyed the pool. Will be back for sure "
The price is CA $215
CA $254 total
includes taxes & fees
Feb 26 - Feb 27
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
9.2 out of 10, Wonderful, (310)
"Great location"
The price is CA $287
CA $327 total
includes taxes & fees
Feb 4 - Feb 5
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.
Exterior

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
Interior

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

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is CA $210
CA $453 total
includes taxes & fees
Feb 11 - Feb 12
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.
Ski In/Out Studio at Okemo on Sachem Trail
Fridge, microwave, oven, stovetop

Ski In/Out Studio at Okemo on Sachem Trail

9.6 out of 10, Exceptional, (10)
"Everything was fantastic! Owner was amazing and so helpful and understanding. We had plenty of room as a family of 5 full over full bunk with full trundle - fireplace was great for ambiance. Ski on ski off so easy access gor a lunch break! Would definitely stay again."
Ski In/Out Studio at Okemo on Sachem Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

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
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.