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

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Windsor bed & breakfast

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

1. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (338 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is AED 453
AED 498 total
includes taxes & fees
10 Nov - 11 Nov
The Jackson
A living room with a grey sectional sofa, a potted plant, and a radiator.

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (85 reviews)
"Very cute spot, good location and staff is super nice:)"
Canada
Rhea
The price is AED 606
AED 666 total
includes taxes & fees
10 Nov - 11 Nov
The Vesper
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

3. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (10 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is AED 829
AED 912 total
includes taxes & fees
9 Nov - 10 Nov
Deer Brook Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

4. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
9.0 out of 10, Wonderful, (108 reviews)
"Beautiful location and all was well"
United States
richard
The price is AED 1,169
AED 1,274 total
includes taxes & fees
25 Nov - 26 Nov
Echo Lake Inn
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

5. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Very clean and easy check in process"
United States
Lana P.
The price is AED 407
AED 643 total
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

6. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (435 reviews)
"It was a fantastic stay and all that we wanted in a charming inn on the mountain."
United States
Marleen
The price is AED 569
AED 689 total
includes taxes & fees
30 Nov - 1 Dec
Snowed Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

7. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
The price is AED 706
AED 769 total
includes taxes & fees
16 Nov - 17 Nov
Stone Hearth Inn and Eatery
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

8. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (295 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is AED 573
AED 625 total
includes taxes & fees
28 Nov - 29 Nov
Harvest Barn Inn
A rustic room with a ping pong table, wooden walls, and a ceiling fan.

9. Dexter's Inn

Dexter's Inn
3.0 star property
Sunapee
9.0 out of 10, Wonderful, (70 reviews)
"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 854
AED 927 total
includes taxes & fees
8 Nov - 9 Nov
Dexter's Inn
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

10. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is AED 309
AED 470 total
includes taxes & fees
11 Nov - 12 Nov
Sleep Woodstock Mobility Impaired Accessible Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

11. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
The price is AED 415
AED 652 total
includes taxes & fees
17 Nov - 18 Nov
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

12. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was a pleasant surprise. Room was spotless and provided everything we needed. Bed was super comfortable and the location was perfect. There is a bit of road noise during the day but none at all at night. Would highly recommend this property."
United States
Mark & Joan S.
The price is AED 415
AED 652 total
includes taxes & fees
17 Nov - 18 Nov
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

13. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 415
AED 652 total
includes taxes & fees
17 Nov - 18 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

14. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
"Old but nice and clean."
United States
James
The price is AED 415
AED 652 total
includes taxes & fees
17 Nov - 18 Nov
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

15. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 383
AED 612 total
includes taxes & fees
30 Nov - 1 Dec
Sleep Woodstock - 2 Double Beds - Dog Friendly
A modern living room with a fireplace, a dining area, and a kitchen.

16. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
The price is AED 555
AED 819 total
includes taxes & fees
3 Dec - 4 Dec
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 374
AED 603 total
includes taxes & fees
30 Nov - 1 Dec
Sleep Woodstock - 2 Double Beds - Dog Friendly
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

18. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 374
AED 603 total
includes taxes & fees
30 Nov - 1 Dec
Sleep Woodstock - 2 Double Beds - Dog Friendly
A bright bedroom with two full sized beds, crisp white linens, and a convenient in-room kitchenette.

19. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 415
AED 652 total
includes taxes & fees
17 Nov - 18 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

20. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 407
AED 643 total
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
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

Six South St Hotel

Six South St Hotel

10/10 Excellent
"Love this hotel"
Aaron 2-night trip
Posted less than an hour ago
Six South St Hotel

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 Paradise Park and Path of Life Garden.
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.
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 Paradise Park are some notable spots. You might put American Precision Museum and Harpoon Brewery 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.