Windsor B&B: Find a Bed and Breakfast 2026

Q: 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.

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

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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

West Woodstock

Laura

includes taxes & fees

24 Sept - 25 Sept

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

2. Stone Hearth Inn and Eatery

Chester

John

includes taxes & fees

24 Sept - 25 Sept

A living room with a grey sectional sofa, a potted plant, and a radiator.

3. The Vesper

Woodstock

Keith

includes taxes & fees

21 Oct - 22 Oct

A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

4. Echo Lake Inn

Plymouth

Michael

includes taxes & fees

13 Oct - 14 Oct

A house with a red roof, a porch with white railings, and a blue door.

5. Woodbridge Inn

Woodstock

eric

includes taxes & fees

27 Sept - 28 Sept

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

6. Harvest Barn Inn

Bellows Falls

Michael

includes taxes & fees

24 Sept - 25 Sept

A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

7. Deer Brook Inn

Woodstock

Laurence

includes taxes & fees

25 Sept - 26 Sept

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Top Windsor Hotel Reviews

Woodstock Inn & Resort

10/10 Excellent

"Wonderful inn! Everything was wonderful: rooms, food, etc!!"

Mountain Sports Inn

8/10 Good

"Jenny @ the front desk was very helpful and kind. The hotel itself is dated. Older beds. Stark shelving in bathrooms though functional. Breakfast was hot and fresh, cook was not.. 😆. Overall we enjoyed our stay and would stay again. Probably request a room away from the main door and towards the back of the property. Cars coming in and out and hallway door noise was above average."

The Jackson

8/10 Good

"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."

Find out more about Windsor

Windsor B&B information

Number of reviews	918
Accommodation	16 B&B
Lowest Price	S$252
Highest Price	S$695

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.

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