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

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Check prices for these dates

Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept
In one month
18 Sept - 20 Sept
In two months
16 Oct - 18 Oct

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, (303 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is £144
includes taxes & fees
25 Aug - 26 Aug
The Jackson
Interior

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (73 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is £141
includes taxes & fees
7 Sept - 8 Sept
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 £201
includes taxes & fees
23 Aug - 24 Aug
Stay At Jimmy's
Exterior

4. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is £111
includes taxes & fees
24 Aug - 25 Aug
Sleep Woodstock - Dog Friendly King Suite
Exterior

5. 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 £169
includes taxes & fees
26 Aug - 27 Aug
Echo Lake Inn
Interior

6. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (6 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is £186
includes taxes & fees
23 Aug - 24 Aug
Deer Brook Inn
Front of property

7. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (122 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is £160
includes taxes & fees
7 Sept - 8 Sept
Stone Hearth Inn and Eatery
Porch

8. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (274 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is £126
includes taxes & fees
31 Aug - 1 Sept
Harvest Barn Inn
Exterior

9. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
The price is £122
includes taxes & fees
1 Sept - 2 Sept
Sleep Woodstock - Dog Friendly King Suite
Exterior

10. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is £119
includes taxes & fees
25 Aug - 26 Aug
Sleep Woodstock - Dog Friendly King Suite
Exterior

11. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is £111
includes taxes & fees
25 Aug - 26 Aug
Sleep Woodstock - Dog Friendly King Suite
Exterior

12. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is £129
includes taxes & fees
25 Aug - 26 Aug
Sleep Woodstock - Dog Friendly King Suite
Exterior

13. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is £123
includes taxes & fees
31 Aug - 1 Sept
Sleep Woodstock - Dog Friendly King Suite
Front of property

14. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (405 reviews)
"On a last last minute trip we found Snowed Inn - super happy we did. Such a welcoming, friendly place. Extremely, clean and well maintained property! Loved our weekend here."
United States
Rebecca
The price is £113
includes taxes & fees
23 Aug - 24 Aug
Snowed Inn
Front of property – evening/night

15. 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 £399
includes taxes & fees
7 Sept - 8 Sept
Woodbridge 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
"Great stay, staff and room was great. Bed was super comfy. Only flaw, they should put a fence up in front of garbage and dumpsters. They are an eye sore."
susan 1-night trip
Posted 4 hours ago
The Shire Woodstock

Find out more about Windsor

Windsor B&B information

Number of reviews
1,335
Accommodation
39 B&B
Lowest Price
£111
Highest Price
£399

Frequently asked questions

Searching for B&Bs in Windsor?
If you're interested in something a little different than the traditional hotel experience, a stay at a bed and breakfast could be the perfect alternative for your trip. While you're here, you can get to know Windsor by exploring its natural beauty—consider stopping at Paradise Park and Path of Life Garden.
Are you considering apartments over traditional hotel rooms?
With attentive service, an atmosphere suited to mingling with other guests and tasty breakfasts, B&Bs provide a truly one-of-a-kind environment.
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 city centre. Deer Brook Inn: 5 rooms. Located 13.4 mi (21.6 km) from the core of Windsor.
When is the best time to book my B&B in Windsor?
When you're planning your getaway to Windsor, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm 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 should 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 map out your trip 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) away from the heart of the city. 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 explore more sights.

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