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Check prices for these dates

Next weekend
Jan 23 - Jan 25
In two weeks
Jan 30 - Feb 1
In one month
Feb 13 - Feb 15
In two months
Mar 13 - Mar 15

Our top choices for Windsor bed & breakfast

Porch
Harvest Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (245 reviews)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Exterior
Mountain Valley Retreat

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (193 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 ￥17,368
￥19,626 total
includes taxes & fees
Jan 13 - Jan 14
Mountain Valley Retreat
Restaurant
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261 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

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is ￥25,164
￥27,679 total
includes taxes & fees
Jan 14 - Jan 15
The Vesper
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46 reviews)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is ￥39,315
￥43,246 total
includes taxes & fees
Jan 13 - Jan 14
Stay At Jimmy's
Front of property
Snowed Inn

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (375 reviews)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
The price is ￥33,708
￥40,785 total
includes taxes & fees
Jan 20 - Jan 21
Snowed Inn
Game room
Dexter's Inn

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 ￥41,446
￥44,969 total
includes taxes & fees
Jan 13 - Jan 14
Dexter's Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (109 reviews)
"So great all around!"
United States
Janet
The price is ￥41,411
￥45,138 total
includes taxes & fees
Jan 14 - Jan 15
Stone Hearth Inn and Eatery
Terrace/patio
Deer Brook Inn

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is ￥43,051
￥47,356 total
includes taxes & fees
Jan 13 - Jan 14
Deer Brook Inn
Exterior
Echo Lake Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98 reviews)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
The price is ￥42,799
￥46,651 total
includes taxes & fees
Jan 13 - Jan 14
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Clean, nice pool and hot tub, and good price!"
Marci 2-night trip
Posted 1 day ago
Pointe at Castle Hill Resort

Find out more about Windsor

Windsor B&B information

Number of reviews
1,411
Accommodation
26 B&B
Lowest Price
￥19,626
Highest Price
￥46,651

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. Stay At Jimmy's: 3 rooms. Located 11.9 mi (19.1 km) from the core of Windsor. Enjoy the jetted tubs and private yard.
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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