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Check prices for these dates

Next weekend
15 May - 17 May
In two weeks
22 May - 24 May
In one month
5 Jun - 7 Jun
In two months
3 Jul - 5 Jul

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, (261 reviews)
"If you're planning a trip to bellows falls or the surrounding areas I would highly recommend the Harvest Barn Inn. The location is beauti"
United States
Gabriel
The price is AED 547
AED 596 total
includes taxes & fees
17 May - 18 May
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, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is AED 698
AED 761 total
includes taxes & fees
12 May - 13 May
Stone Hearth Inn and Eatery
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (60 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
The price is AED 574
AED 631 total
includes taxes & fees
7 May - 8 May
The Vesper
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (279 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is AED 548
AED 603 total
includes taxes & fees
19 May - 20 May
The Jackson
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 274
AED 465 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - 2 Double Beds - Dog Friendly
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
"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 AED 846
AED 931 total
includes taxes & fees
11 May - 12 May
Deer Brook 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 AED 779
AED 849 total
includes taxes & fees
26 May - 27 May
Echo Lake Inn
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 328
AED 524 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 382
AED 584 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - Dog Friendly King Suite
Exterior detail

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is AED 436
AED 638 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock Mobility Impaired Accessible Suite
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 339
AED 537 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 339
AED 537 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 382
AED 584 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 382
AED 584 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 382
AED 584 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock - Dog Friendly King Suite
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 270
AED 461 total
includes taxes & fees
18 May - 19 May
Sleep Woodstock - 2 Double Beds - Dog Friendly
Exterior

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is AED 775
AED 1,066 total
includes taxes & fees
5 Jun - 6 Jun
Sleep Woodstock - Dog Friendly King Suite
Dining room

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (394 reviews)
"Wonderful stay"
United States
Gregory
The price is AED 529
AED 640 total
includes taxes & fees
4 Jun - 5 Jun
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

On The River Inn

On The River Inn

10/10 Excellent
"Lovely location. Very cozy!"
Raja 3-night trip
Posted 9 hours ago
On The River Inn

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.
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.