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

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Check prices for these dates

Next weekend
Jul 3 - Jul 5
In two weeks
Jul 10 - Jul 12
In one month
Jul 24 - Jul 26
In two months
Aug 21 - Aug 23

Our top choices for Windsor bed & breakfast

Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (290 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is ₩247,251
₩271,976 total
includes taxes & fees
Jul 21 - Jul 22
The Jackson
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (267 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
The price is ₩266,866
₩290,884 total
includes taxes & fees
Jun 30 - Jul 1
Harvest Barn Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (66 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
The price is ₩268,585
₩295,443 total
includes taxes & fees
Jul 23 - Jul 24
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, (120 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is ₩320,585
₩349,437 total
includes taxes & fees
Jun 29 - Jun 30
Stone Hearth Inn and Eatery
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (397 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
The price is ₩208,729
₩252,562 total
includes taxes & fees
Jul 9 - Jul 10
Snowed Inn
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 ₩353,749
₩385,586 total
includes taxes & fees
Jun 29 - Jun 30
Echo Lake Inn
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 ₩382,158
₩420,374 total
includes taxes & fees
Jun 28 - Jun 29
Stay At Jimmy's
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 ₩358,981
₩394,879 total
includes taxes & fees
Jun 29 - Jun 30
Deer Brook Inn
Game room

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 ₩405,040
₩439,468 total
includes taxes & fees
Jul 19 - Jul 20
Dexter's 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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Walkable to downtown Woodstock. Loved our room with balcony over looking the river."
Lindsay 2-night trip
Posted 8 hours ago
The Shire Woodstock

Find out more about Windsor

Windsor B&B information

Number of reviews
1,261
Accommodation
16 B&B
Lowest Price
₩252,562
Highest Price
₩439,468

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.
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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