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, (334 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is ฿4,160
฿4,576 total
includes taxes & fees
5 Nov - 6 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 ฿5,571
฿6,128 total
includes taxes & fees
9 Nov - 10 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)
"A+ stay, everything was great about our stay here"
United States
Melissa
The price is ฿4,288
฿5,189 total
includes taxes & fees
28 Oct - 29 Oct
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 ฿7,855
฿8,641 total
includes taxes & fees
1 Nov - 2 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 ฿11,784
฿12,962 total
includes taxes & fees
27 Oct - 28 Oct
Stay At Jimmy's
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

6. 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 ฿7,053
฿7,687 total
includes taxes & fees
16 Nov - 17 Nov
Stone Hearth Inn and Eatery
A rustic room with a ping pong table, wooden walls, and a ceiling fan.

7. 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 ฿7,850
฿8,517 total
includes taxes & fees
8 Nov - 9 Nov
Dexter's Inn
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, (294 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is ฿6,849
฿7,466 total
includes taxes & fees
29 Oct - 30 Oct
Harvest Barn Inn
A house with a red roof, a porch with white railings, and a blue door.

9. 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
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

Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

10/10 Excellent
"Excellent"
Mylene 3-night trip
Posted 2 hours ago
Courtyard by Marriott Hanover Lebanon

Find out more about Windsor

Windsor B&B information

Number of reviews
1,406
Accommodation
16 B&B
Lowest Price
฿4,576
Highest Price
฿12,962

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.

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