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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Resort in Windsor

Woodstock Inn & Resort
Stately room with a checkered floor, classic bench, and fireplace view.

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (530)
"Relaxing "
The price is NZ$829
includes taxes & fees
1 Sept - 2 Sept
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Experience the serene atmosphere of this classic hotel, surrounded by lush greenery and a tranquil pond.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (730)
"Great place great scenery amazing staff"
The price is NZ$229
includes taxes & fees
4 Sept - 5 Sept
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Mountain Edge Suites at Sunapee, Ascend Hotel Collection
Enter through the hotel's inviting entrance, flanked by comfortable benches.

Mountain Edge Suites at Sunapee, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (350)
"Great space. Room was enormous and I enjoyed the continental breakfast."
The price is NZ$304
includes taxes & fees
28 Aug - 29 Aug
Mountain Edge Suites at Sunapee, Ascend Hotel Collection
On The Mountain - 1 - Bedroom - Sleeps 6
Experience the rustic charm of this multi-level space with a cozy seating area and a storefront below.

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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Top Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Exceptionally clean and comfortable. It's an older property fully updated. Great quiet location, nice lawn area and gazebos outside. Huge gathering area in the lobby, nice breakfast. And warm cookies and milk in the evening. Friendly staff. We will be back."
Gail 1-night trip
Posted 8 hours ago
Align Inn Vermont

Frequently asked questions

What can I expect from a resort holiday in Windsor?
Longing for a relaxing escape? You deserve the comforts and luxuries of a resort, where you can find everything you want for your trip—from convenient food and drink options to entertainment and shopping. Browse the resorts in the area and discover the best one for you, whether you picture yourself sitting down to fine dining or hitting the golf course for an afternoon game.
What's a favourite 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 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 centre. Beautiful resort in the heart of Mount Sunapee steps from the mountain. - 18.9 mi (30.5 km) from Windsor. Amenities include a fitness centre. Mount Ascutney Beautiful 1 Bedroom Resort In Brownsville Vermont an IHG Vacation - 4.3 mi (7 km) from Windsor. Access to a fitness centre.
What can I do in Windsor?
Harpoon Brewery, Mt Ascutney State Park and Connecticut River are a few of the interesting sights to visit. A few other attractions you may want to see are American Precision Museum and Path of Life Garden.
What's the seasonal weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm 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) from the heart of the city. Otherwise, look for flights into Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away. To venture out into the surrounding area, hop on a train at Windsor Station.