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Check prices for these dates

Next weekend
18 July - 20 July
In two weeks
25 July - 27 July
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

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, (521)
"Relaxing "
The price is AU$834
includes taxes & fees
10 Aug - 11 Aug
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, (718)
"Excellent property large spacious rooms great restaurant on property"
The price is AU$222
includes taxes & fees
14 July - 15 July
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, (343)
"Always a great time here!"
The price is AU$304
includes taxes & fees
10 Aug - 11 Aug
Mountain Edge Suites at Sunapee, Ascend Hotel Collection
Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM
Cozy cabin with a balcony and chimney, nestled in a winter wonderland.

Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM

Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM
Beautiful resort in the heart of Mount Sunapee steps from the mountain.
Stunning hotel with a central entrance and symmetrical wings, featuring a unique triangular roof design.

Beautiful resort in the heart of Mount Sunapee steps from the mountain.

10.0 out of 10, Exceptional, (1)
"Overall fantastic experience!! Quick communication & extremely friendly staff. Pictures / posting of resort were a bit misleading. Much nicer than what was posted!! All amenities of Ascend hotel were included. "
Beautiful resort in the heart of Mount Sunapee steps from the mountain.
Mount Ascutney Resort in Beautiful Brownsville Vermont Amazing 1 Bedroom
Stunning multi-story building with a central staircase and railings, set against a serene winter backdrop.

Mount Ascutney Resort in Beautiful Brownsville Vermont Amazing 1 Bedroom

Mount Ascutney Resort in Beautiful Brownsville Vermont Amazing 1 Bedroom
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
Mount Ascutney in Brownsville Vermont, A Beautiful Holiday Inn Club Resort
Stunning multi-story building with a central staircase and symmetrical design.

Mount Ascutney in Brownsville Vermont, A Beautiful Holiday Inn Club Resort

Mount Ascutney in Brownsville Vermont, A Beautiful Holiday Inn Club Resort
Mount Ascutney 1 Bedroom in Brownsville Vermont an IHG Holiday Inn Club Resort
Stunning multi-story building with a central staircase and symmetrical design.

Mount Ascutney 1 Bedroom in Brownsville Vermont an IHG Holiday Inn Club Resort

Mount Ascutney 1 Bedroom in Brownsville Vermont an IHG Holiday Inn Club Resort
Mount Ascutney Beautiful 1 Bedroom Resort In Brownsville Vermont an IHG Vacation
Stunning multi-story building with a central staircase and second-floor entrance, offering a warm and inviting atmosphere.

Mount Ascutney Beautiful 1 Bedroom Resort In Brownsville Vermont an IHG Vacation

Mount Ascutney Beautiful 1 Bedroom Resort In Brownsville Vermont an IHG Vacation
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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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. Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM - 22.6 mi (36.3 km) from Windsor. Amenities include 1 hot 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 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 Windsor Public Library.
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.