Windsor B&B: Best Windsor Bed and Breakfast

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. 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.

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

Brian

includes taxes & fees

8 Sept - 9 Sept

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

2. The Vesper

Woodstock

Keith

includes taxes & fees

7 Sept - 8 Sept

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

3. Harvest Barn Inn

Bellows Falls

Michael

includes taxes & fees

2 Sept - 3 Sept

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

4. Stone Hearth Inn and Eatery

Chester

Kathleen

includes taxes & fees

3 Sept - 4 Sept

A row of cabins with a snow-covered ground and trees in the background.

5. Sleep Woodstock - Dog Friendly King Suite

Woodstock

David M.

includes taxes & fees

7 Sept - 8 Sept

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

6. Deer Brook Inn

Woodstock

Laurence

includes taxes & fees

6 Sept - 7 Sept

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

7. Echo Lake Inn

Plymouth

Michael

includes taxes & fees

8 Sept - 9 Sept

A modern fitness center with exercise equipment, mirrors, and a reception area.

8. Stay At Jimmy's

Woodstock

Jeanne

includes taxes & fees

10 Sept - 11 Sept

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Top Windsor Hotel Reviews

Woodstock Inn & Resort

10/10 Excellent

"Our room was beautiful, clean, and quiet. The bed was comfortable, and the amenities in the bathroom were a real indulgence."

On The River Inn

10/10 Excellent

"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."

Find out more about Windsor

Windsor B&B information

Number of reviews	1,277
Accommodation	38 B&B
Lowest Price	AU$209
Highest Price	AU$760

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 Harpoon Brewery 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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