Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
21 Nov - 23 Nov
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28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

B&B in Windsor

Exterior
Mountain Valley Retreat

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
The price is AED 404
AED 457 total
includes taxes & fees
16 Nov - 17 Nov
Mountain Valley Retreat
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (247)
"The room, the staff, the amenities were what we were hoping for. The Jackson is a great place to stay! "
United States
Frederick
The Jackson
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (17)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
United States
Nevets
The price is AED 312
AED 555 total
includes taxes & fees
16 Nov - 17 Nov
Room in Historic Inn! 20 Minutes to Okemo!
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Room was super quiet and clean. "
United States
Ernest
The price is AED 683
AED 744 total
includes taxes & fees
16 Dec - 17 Dec
Stone Hearth Inn and Eatery
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
The price is AED 731
AED 804 total
includes taxes & fees
16 Nov - 17 Nov
Stay At Jimmy's
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Chester Depot
9.0 out of 10, Wonderful, (2)
"Yes, wonderful location and stay"
United States
Sharon
The price is AED 327
AED 592 total
includes taxes & fees
16 Nov - 17 Nov
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi
The Vesper

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (44)
"The Vesper was a great find in Woodstock VT. Close to downtown to walk to everything. Rooms are spotless and charming. We would definitely stay at the Vesper BnB again."
United States
Kevin
The price is AED 565
AED 621 total
includes taxes & fees
17 Nov - 18 Nov
The Vesper
Front of property
Snowed Inn

Snowed Inn

3.5 star property
Killington
9.8 out of 10, Exceptional, (370)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
United States
Bradford
The price is AED 757
AED 916 total
includes taxes & fees
3 Dec - 4 Dec
Snowed Inn
Game room
Dexter's Inn

Dexter's Inn

3.0 star property
Sunapee
8.8 out of 10, Excellent, (70)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
United States
Lisa
The price is AED 909
AED 986 total
includes taxes & fees
1 Dec - 2 Dec
Dexter's Inn
Front of property - evening/night
Woodbridge Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (66)
"Amazing stay at a beautiful location. Would definitely stay again. "
United States
Aaron
The price is AED 1,634
AED 1,798 total
includes taxes & fees
11 Dec - 12 Dec
Woodbridge Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"The staff was super friendly, and welcoming "
United States
Janet
The price is AED 942
AED 1,027 total
includes taxes & fees
16 Dec - 17 Dec
Echo Lake Inn
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
The price is AED 511
AED 831 total
includes taxes & fees
16 Nov - 17 Nov
King & Queen Suite in Historic Inn Circa 1780
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
The price is AED 400
AED 654 total
includes taxes & fees
16 Nov - 17 Nov
Honeymoon Suite with Jacuzzi Tub in Historic Inn
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
"The Inn was totally redone in 2019. Looks great. Spotless interior. Friendly staff, delicious cookies. All at a very reasonable price. What else do you need?"
Leigh 1-night trip
Posted 2 days ago
Align Inn Vermont

Frequently asked questions

Searching for B&Bs in Windsor?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your getaway. While you're here, you can get to know Windsor by exploring its natural beauty. Consider a stop by Path of Life Garden and Paradise Park.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to interact with the owner, and hearty breakfasts, B&Bs offer a unique setting.
What are the best bed and breakfasts in Windsor?
Here are some well-liked B&Bs in the area: The Jackson: 11 rooms. 12.2 mi (19.7 km) from the heart of Windsor. Enjoy the designer toiletries and library. The Vesper: 9 rooms. Situated 12 mi (19.3 km) from the heart of Windsor. Stay At Jimmy's: 3 rooms. Located 11.9 mi (19.1 km) from the core of Windsor. Enjoy the jetted tubs and private yard.
What's the best time of year to book my B&B in Windsor?
When you're planning your stay in Windsor, year-round temperatures and rainfall may be important factors to consider. 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 is there to do in Windsor?
When you want to spend some time in the great outdoors, Connecticut River and Path of Life Garden are some notable spots. You might put Harpoon Brewery and Mt Ascutney State Park on your list if you want to see more of the area.
How can I get to and around Windsor?
You can plan your excursions in and around Windsor ahead of time with these transportation options. Fly into Lebanon, NH (LEB-Lebanon Municipal), which is located 10.7 mi (17.3 km) from the city center. Otherwise, you can search for flights to Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.