20 Best B&B in Windsor, VT - Bed and Breakfast from ￥21,454

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

Ava

￥21,454 total

includes taxes & fees

Nov 3 - Nov 4

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

2. The Vesper

Woodstock

Keith

￥28,794 total

includes taxes & fees

Nov 10 - Nov 11

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

3. Deer Brook Inn

Woodstock

Laurence

￥40,514 total

includes taxes & fees

Nov 2 - Nov 3

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

4. Stay At Jimmy's

Woodstock

Jeanne

￥52,176 total

includes taxes & fees

Oct 29 - Oct 30

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

5. Sleep Woodstock - Dog Friendly King Suite

Woodstock

David M.

￥27,834 total

includes taxes & fees

Nov 9 - Nov 10

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

6. Woodbridge Inn

Woodstock

Michelle

￥86,199 total

includes taxes & fees

Oct 20 - Oct 21

A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

7. Snowed Inn

Killington

Melissa

￥24,327 total

includes taxes & fees

Oct 25 - Oct 26

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

8. Echo Lake Inn

Plymouth

Amanda

￥53,890 total

includes taxes & fees

Oct 14 - Oct 15

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Top Windsor Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"I can’t say enough about how enjoyable it was! Will be back!"

Mountain Meadows Lodge

10/10 Excellent

"As soon as we arrived we felt welcomed into a home from home. Everything we could possibly need was provided for. The view of the lake so beautiful and our room with the terrace and view couldn’t have been better. The breakfast was superb as were the goodies left for us during the day. The very comfortable sitting room with the fireplace offered a superb view across the lawns to the lake. We loved the different fires outside in the evening and much enjoyed the table football. Thank you for looking after us so well and making it such a happy stay for us."

On The River Inn

10/10 Excellent

"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."

Find out more about Windsor

Windsor B&B information

Number of reviews	812
Accommodation	38 B&B
Lowest Price	￥21,454
Highest Price	￥86,199

Frequently asked questions

Searching for B&Bs in Windsor?

If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your getaway. While you're here, you can get to know Windsor by exploring its natural beauty. Consider a stop by Paradise Park and Path of Life Garden.

Are you thinking about a B&B for your stay?

With attentive service, opportunities to interact with the owner, and hearty breakfasts, B&Bs offer a unique setting.

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.

What's the best time of year to book my B&B in Windsor?

When you're planning your stay in Windsor, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches 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 might 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 plan your excursions 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) from the city center. 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 take in more sights.

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