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Check prices for these dates

Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar
In one month
13 Mar - 15 Mar
In two months
10 Apr - 12 Apr

Our top choices for Windsor bed & breakfast

Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (249 reviews)
"Everything was great. Awesome hosts, room, common areas and a fabulous breakfast. Can’t recommend too highly."
United States
Mark
Harvest Barn Inn
Property grounds

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (196 reviews)
"Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!"
United States
Steven
The price is RM431
RM487 total
includes taxes & fees
17 Feb - 18 Feb
Mountain Valley Retreat
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (265 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is RM727
RM800 total
includes taxes & fees
16 Feb - 17 Feb
The Vesper
Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (112 reviews)
"So great all around!"
United States
Janet
The price is RM818
RM892 total
includes taxes & fees
16 Feb - 17 Feb
Stone Hearth Inn and Eatery
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is RM920
RM1,012 total
includes taxes & fees
3 Mar - 4 Mar
Deer Brook Inn
Building design

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 RM1,028
RM1,115 total
includes taxes & fees
15 Feb - 16 Feb
Dexter's Inn
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (382 reviews)
"Wonderful stay"
United States
Gregory
The price is RM1,118
RM1,353 total
includes taxes & fees
22 Feb - 23 Feb
Snowed Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is RM1,171
RM1,288 total
includes taxes & fees
16 Feb - 17 Feb
Stay At Jimmy's
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (99 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 RM1,142
RM1,244 total
includes taxes & fees
23 Feb - 24 Feb
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"People went out of their way to help My wife needed distilled water for her C-Pap machine the staff went out to store so she could have some. Restaurant was great Room was clean "
Dennis 2-night trip
Posted 2 days ago
The Mountain Inn at Killington

Find out more about Windsor

Windsor B&B information

Number of reviews
1,437
Accommodation
16 B&B
Lowest Price
RM487
Highest Price
RM1,353

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: Windsor Mansion Inn: 17 rooms. 0.9 mi (1.5 km) from the heart of Windsor. Enjoy the unique decor and library. The Jackson: 11 rooms. Situated 12.2 mi (19.7 km) from the heart of Windsor. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 12 mi (19.3 km) from the city centre.
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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