Search Bed and Breakfast in Windsor

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Windsor bed & breakfast

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

1. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (338 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is S$174
includes taxes & fees
11 Nov - 12 Nov
The Jackson
A living room with a grey sectional sofa, a potted plant, and a radiator.

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (85 reviews)
"Very cute spot, good location and staff is super nice:)"
Canada
Rhea
The price is S$232
includes taxes & fees
9 Nov - 10 Nov
The Vesper
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

3. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (10 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is S$321
includes taxes & fees
9 Nov - 10 Nov
Deer Brook Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

4. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
9.0 out of 10, Wonderful, (108 reviews)
"Beautiful location and all was well"
United States
richard
The price is S$443
includes taxes & fees
7 Dec - 8 Dec
Echo Lake Inn
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

5. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (436 reviews)
"It was a fantastic stay and all that we wanted in a charming inn on the mountain."
United States
Marleen
The price is S$203
includes taxes & fees
6 Dec - 7 Dec
Snowed Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

6. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
The price is S$282
includes taxes & fees
19 Nov - 20 Nov
Stone Hearth Inn and Eatery
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (296 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is S$220
includes taxes & fees
28 Nov - 29 Nov
Harvest Barn Inn
A wooden interior with a fireplace, bookshelves, and a dining area.

8. Dexter's Inn

Dexter's Inn
3.0 star property
Sunapee
9.0 out of 10, Wonderful, (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 S$316
includes taxes & fees
8 Nov - 9 Nov
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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Learn more about Windsor

Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterwards, savour craft brews at Harpoon Brewery or hike the scenic trails of Mt Ascutney State Park for breathtaking views.

See all hotels in Windsor
A covered bridge over a river with lush greenery and a clear sky.

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.

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.