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Check prices for these dates

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun
In one month
3 Jul - 5 Jul
In two months
31 Jul - 2 Aug

Our top choices for Windsor bed & breakfast

Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is 6.555.921 ₫
7.211.514 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Stay At Jimmy's
Lobby sitting area

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (396 reviews)
"We had a really amazing experience. We really enjoyed ourselves. It was very clean and all the amenities were wonderful.."
United States
Domenick
The price is 3.212.138 ₫
3.886.687 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Snowed Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (266 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
The price is 4.578.087 ₫
4.990.115 ₫ total
includes taxes & fees
15 Jun - 16 Jun
Harvest Barn Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (284 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is 4.786.612 ₫
5.265.273 ₫ total
includes taxes & fees
25 Jun - 26 Jun
The Jackson
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (2 reviews)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is 6.125.442 ₫
6.737.987 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Deer Brook Inn
Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is 5.499.628 ₫
5.994.595 ₫ total
includes taxes & fees
9 Jun - 10 Jun
Stone Hearth Inn and Eatery
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (62 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
The price is 4.607.575 ₫
5.068.333 ₫ total
includes taxes & fees
10 Jun - 11 Jun
The Vesper
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is 6.068.571 ₫
6.614.742 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Echo Lake 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

Align Inn Vermont

Align Inn Vermont

8/10 Good
"Very clean room, breakfast regular, staff friendly."
Johnson 2-night trip
Posted 4 hours ago
Align Inn Vermont

Find out more about Windsor

Windsor B&B information

Number of reviews
1,177
Accommodation
15 B&B
Lowest Price
3.886.687 ₫
Highest Price
7.211.514 ₫

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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