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

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Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec

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, (336 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is €122
includes taxes & fees
3 Nov - 4 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, (82 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is €163
includes taxes & fees
29 Nov - 30 Nov
The Vesper
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

3. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (432 reviews)
"It was a fantastic stay and all that we wanted in a charming inn on the mountain."
United States
Marleen
The price is €161
includes taxes & fees
31 Oct - 1 Nov
Snowed Inn
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

4. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (9 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is €229
includes taxes & fees
8 Nov - 9 Nov
Deer Brook Inn
A modern fitness center with exercise equipment, mirrors, and a reception area.

5. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (55 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
The price is €444
includes taxes & fees
30 Oct - 31 Oct
Stay At Jimmy's
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

6. 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 €157
includes taxes & fees
2 Nov - 3 Nov
Sleep Woodstock - Dog Friendly King Suite
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 €229
includes taxes & fees
15 Nov - 16 Nov
Stone Hearth Inn and Eatery
A rustic room with a ping pong table, wooden walls, and a ceiling fan.

8. Dexter's Inn

Dexter's Inn
3.0 star property
Sunapee
8.8 out of 10, Excellent, (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 €226
includes taxes & fees
12 Nov - 13 Nov
Dexter's Inn
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

9. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (294 reviews)
"Staff was excellent and river views were amazing"
United States
John
Harvest Barn Inn
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

10. 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 €162
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a fireplace, a dining area, and a kitchen.

11. 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 €162
includes taxes & fees
16 Nov - 17 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)
"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 €158
includes taxes & fees
2 Nov - 3 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 - 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 €162
includes taxes & fees
9 Nov - 10 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.

14. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is €128
includes taxes & fees
19 Nov - 20 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.

15. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is €169
includes taxes & fees
9 Nov - 10 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.

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is €218
includes taxes & fees
15 Nov - 16 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A house with a red roof, a porch with white railings, and a blue door.

17. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (71 reviews)
"We loved our stay here. Everyone was so nice. The beds were incredibly comfortable. We arrived in the late afternoon in time for happy hour. We sat outside near the fire pit and watched the sunset behind the mountains. It’s a little outside of Woodstock but very convenient."
United States
Michelle
Woodbridge Inn
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 €139
includes taxes & fees
1 Nov - 2 Nov
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 €218
includes taxes & fees
15 Nov - 16 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 - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is €157
includes taxes & fees
4 Nov - 5 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
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

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

10/10 Excellent
"Perfect"
Kaleb 2-night trip
Posted 2 hours ago
Hideaway Inn Mt.Sunapee

Find out more about Windsor

Windsor B&B information

Number of reviews
1,412
Accommodation
38 B&B
Lowest Price
€122
Highest Price
€444

Frequently asked questions

Searching for B&Bs in Windsor?
If you're interested in something a little different than the traditional hotel experience, a stay at a bed and breakfast could be the perfect alternative for your trip. While you're here, you can get to know Windsor by exploring its natural beauty—consider stopping at Paradise Park and Path of Life Garden.
Are you considering apartments over traditional hotel rooms?
With attentive service, an atmosphere suited to mingling with other guests and tasty breakfasts, B&Bs provide a truly one-of-a-kind environment.
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.
When is the best time to book my B&B in Windsor?
When you're planning your getaway to Windsor, year-round temperatures and rainfall may be important factors to consider. 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 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 should 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 map out your trip 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) away from the heart of the city. 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 explore more sights.