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

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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 3.194.822 ₫
3.514.304 ₫ total
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, (80 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is 4.268.859 ₫
4.695.745 ₫ 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, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is 6.019.121 ₫
6.621.033 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Deer Brook Inn
A modern fitness center with exercise equipment, mirrors, and a reception area.

4. 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 7.735.728 ₫
8.509.301 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Stay At Jimmy's
A house with a red roof, a porch with white railings, and a blue door.

5. 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 12.806.640 ₫
14.087.304 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Woodbridge Inn
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, (423 reviews)
"A+ stay, everything was great about our stay here"
United States
Melissa
The price is 3.285.744 ₫
3.975.750 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Snowed Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

7. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.8 out of 10, Excellent, (106 reviews)
"Beautiful property! The charm and character of the place were amazing. Staff was friendly and very helpful. Rooms were quaint and well appointed, clean with comfy beds!"
United States
Amanda
The price is 8.487.310 ₫
9.251.168 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Echo Lake Inn
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 6.015.240 ₫
6.526.535 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Dexter's 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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"I can’t say enough about how enjoyable it was! Will be back!"
Allison 3-night trip
Posted 4 hours ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Windsor

Windsor B&B information

Number of reviews
810
Accommodation
17 B&B
Lowest Price
3.514.304 ₫
Highest Price
14.087.304 ₫

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.
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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