Windsor B&B | Expedia

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

RM553 total

includes taxes & fees

3 Nov - 4 Nov

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

2. The Vesper

Woodstock

Keith

RM741 total

includes taxes & fees

15 Nov - 16 Nov

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

3. Stay At Jimmy's

Woodstock

Jeanne

RM1,343 total

includes taxes & fees

29 Oct - 30 Oct

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

4. Deer Brook Inn

Woodstock

Laurence

RM1,045 total

includes taxes & fees

1 Nov - 2 Nov

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

5. Woodbridge Inn

Woodstock

Michelle

RM2,223 total

includes taxes & fees

20 Oct - 21 Oct

A rustic room with a ping pong table, wooden walls, and a ceiling fan.

6. Dexter's Inn

Sunapee

Lisa

RM1,031 total

includes taxes & fees

8 Nov - 9 Nov

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

7. Stone Hearth Inn and Eatery

Chester

John

RM1,040 total

includes taxes & fees

15 Nov - 16 Nov

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

8. Snowed Inn

Killington

Melissa

RM627 total

includes taxes & fees

28 Oct - 29 Oct

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Top Windsor Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

"Great views and quiet location. Comfortable communal areas, great walks around the surrounding forests and a wonderful spot to relax next to the lake. A short drive to Killington and all its attractions. Loved the cookies."

Pointe at Castle Hill Resort

10/10 Excellent

"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."

Find out more about Windsor

Windsor B&B information

Number of reviews	834
Accommodation	16 B&B
Lowest Price	RM553
Highest Price	RM2,223

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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