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

Book a Windsor Resort

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Windsor resorts

A large, multi-story hotel with a central courtyard featuring a pond and a fountain.

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, (868 reviews)
"Laundry room in the building, get beds."
United States
Gene
The price is ￥22,094
￥26,705 total
includes taxes & fees
Aug 25 - Aug 26
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A stone-clad building entrance with a covered patio and benches.

2. 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, (438 reviews)
"Lovely hotel, huge suite. Pool and hot tub great. We enjoyed breakfast."
United Kingdom
Rachel
The price is ￥21,481
￥25,895 total
includes taxes & fees
Aug 31 - Sep 1
Mountain Edge Suites at Sunapee, an Ascend Collection Hotel
A room with a checkered floor, a bench, and a fireplace.

3. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (599 reviews)
"As always - best hotel in Vermont."
United States
ben
The price is ￥65,011
￥78,506 total
includes taxes & fees
Sep 7 - Sep 8
Woodstock Inn & Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Great location for a college visit & Quechee Gorge. Clean, quiet & convenient"
Maria Belinda 1-night trip
Posted 1 hour ago
Align Inn Vermont

Find out more about Windsor

Windsor Resorts information

Number of reviews
1,467
Accommodation
3 Resorts
Lowest Price
￥25,895
Highest Price
￥78,506

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 2 indoor pools, free pool cabanas, and fitness center.
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.

Explore a world of travel with Expedia