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

Search Windsor Bed & Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
In one month
13 Nov - 15 Nov
In two months
11 Dec - 13 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, (331 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is AU$195
includes taxes & fees
16 Nov - 17 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, (81 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is AU$261
includes taxes & fees
9 Nov - 10 Nov
The Vesper
A modern fitness center with exercise equipment, mirrors, and a reception area.

3. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (54 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 AU$473
includes taxes & fees
29 Oct - 30 Oct
Stay At Jimmy's
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 AU$368
includes taxes & fees
1 Nov - 2 Nov
Deer Brook Inn
A row of cabins with a snow-covered ground and trees 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)
"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 AU$255
includes taxes & fees
27 Oct - 28 Oct
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

6. 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 AU$255
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.

7. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is AU$192
includes taxes & fees
16 Nov - 17 Nov
Sleep Woodstock Mobility Impaired Accessible Suite
A row of cabins with a snow-covered ground and trees in the background.

8. 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 AU$255
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

9. 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 AU$255
includes taxes & fees
16 Nov - 17 Nov
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

10. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AU$255
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A house with a red roof, a porch with white railings, and a blue door.

11. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (70 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
The price is AU$784
includes taxes & fees
20 Oct - 21 Oct
Woodbridge Inn
A row of cabins with a snow-covered ground and trees in the background.

12. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AU$255
includes taxes & fees
16 Nov - 17 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

13. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AU$224
includes taxes & fees
20 Oct - 21 Oct
Sleep Woodstock - 2 Double Beds - Dog Friendly
A bright bedroom with one king bed, crisp white linens, and a convenient in-room kitchenette.

14. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AU$255
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

15. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AU$255
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AU$242
includes taxes & fees
4 Nov - 5 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AU$255
includes taxes & fees
27 Oct - 28 Oct
Sleep Woodstock - 2 Double Beds - Dog Friendly
A rustic room with a ping pong table, wooden walls, and a ceiling fan.

18. 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 AU$301
includes taxes & fees
11 Nov - 12 Nov
Dexter's Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

19. 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 AU$279
includes taxes & fees
17 Nov - 18 Nov
Stone Hearth Inn and Eatery
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

20. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (423 reviews)
"A+ stay, everything was great about our stay here"
United States
Melissa
The price is AU$221
includes taxes & fees
25 Oct - 26 Oct
Snowed 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."
Adriana 2-night trip
Posted less than an hour ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Windsor

Windsor B&B information

Number of reviews
840
Accommodation
38 B&B
Lowest Price
AU$192
Highest Price
AU$784

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.

Explore a world of travel with Expedia