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

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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 NT$3,933
NT$4,326 total
includes taxes & fees
Nov 3 - Nov 4
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 NT$5,267
NT$5,794 total
includes taxes & fees
Nov 10 - Nov 11
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 NT$7,427
NT$8,170 total
includes taxes & fees
Nov 1 - Nov 2
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 NT$9,545
NT$10,500 total
includes taxes & fees
Oct 29 - Oct 30
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 NT$15,802
NT$17,383 total
includes taxes & fees
Oct 22 - Oct 23
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)
The price is NT$4,054
NT$4,906 total
includes taxes & fees
Oct 25 - Oct 26
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
Echo Lake Inn
A grassy field with a small building and trees in the background.

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 NT$7,422
NT$8,053 total
includes taxes & fees
Nov 8 - Nov 9
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Very much enjoyed our stay! The property is beautiful and hosts lovely. We loved the breakfast pancakes and chocolate chip cookies! Easy access to hiking trails. Would definitely stay here again!"
Sharon 2-night trip
Posted less than an hour ago
Mountain Meadows Lodge

Find out more about Windsor

Windsor B&B information

Number of reviews
810
Accommodation
16 B&B
Lowest Price
NT$4,326
Highest Price
NT$17,383

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.

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