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

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Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Windsor bed & breakfast

Restaurant

1. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (301 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is ₩227,554
₩250,309 total
includes taxes & fees
Aug 25 - Aug 26
The Jackson
Interior

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (70 reviews)
"Great easy parking and seamless entry. Good stay."
United States
Terry
The price is ₩247,188
₩271,907 total
includes taxes & fees
Aug 18 - Aug 19
The Vesper
Front of property

3. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (50 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is ₩351,713
₩386,884 total
includes taxes & fees
Aug 23 - Aug 24
Stay At Jimmy's
Exterior

4. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (101 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 ₩325,567
₩354,868 total
includes taxes & fees
Aug 18 - Aug 19
Echo Lake Inn
Interior

5. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (4 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 ₩328,618
₩361,481 total
includes taxes & fees
Aug 13 - Aug 14
Deer Brook Inn
Front of property

6. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (121 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is ₩295,044
₩321,598 total
includes taxes & fees
Aug 13 - Aug 14
Stone Hearth Inn and Eatery
Porch

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (273 reviews)
"Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn"
Canada
Natalie
The price is ₩245,605
₩267,710 total
includes taxes & fees
Aug 25 - Aug 26
Harvest Barn Inn
Front of property - evening/night

8. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67 reviews)
"Great place to stay"
United States
eric
The price is ₩701,910
₩772,101 total
includes taxes & fees
Sep 8 - Sep 9
Woodbridge Inn
Front of property

9. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (402 reviews)
"Everything was nice"
United States
Rouslan
The price is ₩179,388
₩217,059 total
includes taxes & fees
Aug 17 - Aug 18
Snowed 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
"Adorable, clean place in a great location."
mary 1-night trip
Posted 1 hour ago
The Shire Woodstock

Find out more about Windsor

Windsor B&B information

Number of reviews
1,197
Accommodation
16 B&B
Lowest Price
₩217,059
Highest Price
₩772,101

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. 12 mi (19.3 km) from the downtown core. Deer Brook Inn: 5 rooms. Located 13.4 mi (21.6 km) from the core 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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