A snow-covered river valley with a bridge and a town.

Best Resorts in Windsor

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Windsor resorts

A multi-story hotel with a central courtyard and a reflective water feature.

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (890 reviews)
"Beautiful resort with amazing beds! Very comfortable."
United States
Sara
$154 nightly
The price is $168
Oct 27 - Oct 28
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A room with a checkered floor, a bench, and a fireplace.

2. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (621 reviews)
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
United States
Ann
$409 nightly
The price is $450
Nov 16 - Nov 17
Total with taxes and fees
Woodstock Inn & Resort
A stone-clad building entrance with a covered patio and benches.

3. Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
3.0 star property
Newbury
9.2 out of 10, Wonderful, (449 reviews)
"Mountain Edge is ideal for long weekend or week long stays in Sunapee."
United States
Jen
$172 nightly
The price is $187
Nov 22 - Nov 23
Total with taxes and fees
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"We had soooooo much fun and will definitely be back!!!! 10/10 all around :)"
Bridget 2-night trip
Posted 6 hours ago
The Mountain Inn at Killington

Find out more about Windsor

Windsor Resorts information

Number of reviews
890
Accommodation
3 Resorts
Lowest Price
$168
Highest Price
$450

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 bar, an outdoor tennis court, and a restaurant. Mountain Edge Suites at Sunapee, an Ascend Collection Hotel - 18.8 mi (30.3 km) from Windsor. Enjoy the free pool cabanas, fitness center, and terrace.
What can I do in Windsor?
American Precision Museum, Harpoon Brewery, and Mt Ascutney State Park are a few of the interesting sights to visit. A few other attractions you may want to see are Connecticut River and Brownsville Trail.
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.

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