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

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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, (323 reviews)
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
United States
Laura
The price is RM914
RM1,005 total
includes taxes & fees
1 Nov - 2 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 RM673
RM741 total
includes taxes & fees
25 Oct - 26 Oct
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 RM1,220
RM1,342 total
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, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
Deer Brook Inn
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, (68 reviews)
"Great place to stay"
United States
eric
The price is RM2,020
RM2,222 total
includes taxes & fees
20 Oct - 21 Oct
Woodbridge Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

6. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (104 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 RM1,339
RM1,460 total
includes taxes & fees
13 Oct - 14 Oct
Echo Lake Inn
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, (128 reviews)
"Wonderful staff and restaurant"
United States
John
The price is RM1,151
RM1,254 total
includes taxes & fees
5 Oct - 6 Oct
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.

8. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (415 reviews)
"Great hot tub and breakfast."
United States
Brendan
The price is RM563
RM681 total
includes taxes & fees
25 Oct - 26 Oct
Snowed 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, (287 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is RM621
RM677 total
includes taxes & fees
1 Nov - 2 Nov
Harvest Barn 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
"This place is awesome! From the location to the breakfast provided( and snacks available all day!), there is plenty to do without ever leaving the property"
Kevin 3-night trip
Posted 9 hours ago
Mountain Meadows Lodge

Find out more about Windsor

Windsor B&B information

Number of reviews
1,466
Accommodation
16 B&B
Lowest Price
RM677
Highest Price
RM2,222

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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