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

Bed and Breakfast in Windsor

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sept - 6 Sept
In two months
2 Oct - 4 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, (300 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is NZ$301
includes taxes & fees
23 Aug - 24 Aug
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 NZ$327
includes taxes & fees
18 Aug - 19 Aug
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 NZ$465
includes taxes & fees
17 Aug - 18 Aug
Stay At Jimmy's
Exterior

4. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is NZ$322
includes taxes & fees
25 Aug - 26 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, (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 NZ$405
includes taxes & fees
17 Aug - 18 Aug
Echo Lake Inn
Interior

6. 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 NZ$430
includes taxes & fees
17 Aug - 18 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, (121 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 NZ$383
includes taxes & fees
17 Aug - 18 Aug
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, (270 reviews)
"Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn"
Canada
Natalie
The price is NZ$303
includes taxes & fees
17 Aug - 18 Aug
Harvest Barn 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 NZ$261
includes taxes & fees
12 Aug - 13 Aug
Snowed Inn
Exterior

10. 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 NZ$318
includes taxes & fees
23 Aug - 24 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 NZ$269
includes taxes & fees
13 Aug - 14 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 NZ$275
includes taxes & fees
19 Aug - 20 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 NZ$298
includes taxes & fees
18 Aug - 19 Aug
Sleep Woodstock - Dog Friendly King Suite
Exterior

14. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
The price is NZ$304
includes taxes & fees
16 Aug - 17 Aug
Sleep Woodstock - Dog Friendly King Suite
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

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"The room was roomy and clean. The hotel was super clean. The front desk staff was very helpful. The pool was excellent and the breakfast was delightful."
John 2-night trip
Posted 11 hours ago
Fireside Inn & Suites West Lebanon

Find out more about Windsor

Windsor B&B information

Number of reviews
1,093
Accommodation
39 B&B
Lowest Price
NZ$261
Highest Price
NZ$465

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. Situated 12 mi (19.3 km) from the heart of Windsor. 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 Mt Ascutney State Park 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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