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Check prices for these dates

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

Our top choices for Windsor bed & breakfast

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 P6,392
P7,223 total
includes taxes & fees
Mar 2 - Mar 3
Mountain Valley Retreat
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
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 P12,138
P13,230 total
includes taxes & fees
Feb 23 - Feb 24
Stone Hearth Inn and Eatery
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 P10,786
P11,865 total
includes taxes & fees
Feb 16 - Feb 17
The Vesper
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 P15,253
P16,550 total
includes taxes & fees
Feb 15 - Feb 16
Dexter's Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is P13,655
P15,021 total
includes taxes & fees
Mar 3 - Mar 4
Deer Brook 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 P17,374
P19,112 total
includes taxes & fees
Feb 16 - Feb 17
Stay At Jimmy's
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 P16,584
P20,067 total
includes taxes & fees
Feb 22 - Feb 23
Snowed Inn
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 P16,936
P18,460 total
includes taxes & fees
Feb 23 - Feb 24
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

On The River Inn

On The River Inn

10/10 Excellent
"Room was excellent! Very clean and very comfortable. Bed and comforter were fantastic. Beautiful view in the back . The whole hotel is so nicely dec with antics all around. Have stayed few before will continue to come back. Sent my daughter here as well As a little gift. "
Wendy 1-night trip
Posted 3 days ago
On The River Inn

Find out more about Windsor

Windsor B&B information

Number of reviews
1,437
Accommodation
16 B&B
Lowest Price
P7,223
Highest Price
P20,067

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