Top B&B in Windsor in 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. 12 mi (19.3 km) from the city centre.

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Our top choices for Windsor bed & breakfast

Harvest Barn Inn

Bellows Falls

Mark

฿6,226 total

includes taxes & fees

16 Jun - 17 Jun

The Jackson

West Woodstock

Courtney

฿5,682 total

includes taxes & fees

24 Jun - 25 Jun

Stone Hearth Inn and Eatery

Chester

Olena

฿7,467 total

includes taxes & fees

17 Jun - 18 Jun

The Vesper

Woodstock

Melissa

฿6,324 total

includes taxes & fees

14 Jun - 15 Jun

Stay At Jimmy's

Woodstock

Heather

฿8,998 total

includes taxes & fees

10 Jun - 11 Jun

Deer Brook Inn

Woodstock

Sara

฿8,407 total

includes taxes & fees

10 Jun - 11 Jun

Echo Lake Inn

Plymouth

Danielle

฿8,239 total

includes taxes & fees

16 Jun - 17 Jun

Snowed Inn

Killington

Martin

฿5,128 total

includes taxes & fees

16 Jun - 17 Jun

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Top Windsor Hotel Reviews

Hotel Coolidge

10/10 Excellent

"The historical charm was magnificent ! The staff was very helpful."

Align Inn Vermont

10/10 Excellent

"To be completely honest, I was surprised by how great this place was. I visit Quechee often and usually stay with friends. I will absolutely stay here again if necessary. Everything was clean, the breakfast was actually really great and the pool was clean. Sure, it is a typical motel, yet it was better than most that I've stayed at."

Hideaway Inn Mt.Sunapee

10/10 Excellent

"We walked in and the place is so cute and rustic. There was a luggage rack for us to bring our bags in. There was a freezer chest with free bagged ice in it which came in handy for our cooler for after our race. There is also a little coffee bar in the lobby. The room was well decorated, comfortable beds, clean linens and clean bathroom. There was soap and shampoo and conditioner. Also had a hair dryer. The shower had great pressure and was hot. Highly recommend this place for a short or long stay. We slept well and it was very comfortable."

Hampton Inn White River Junction

8/10 Good

"This hotel was clean, comfortable, and well-maintained, making for a pleasant stay. Its convenient location provided easy access to Dartmouth College and all that the Upper Valley has to offer, making it an ideal choice for visitors to the area. The staff were warm, welcoming, and genuinely committed to ensuring guests felt at home from check-in to departure. The complimentary breakfast was one of the best I have experienced. There was a variety of fresh, delicious options that exceeded expectations."

Find out more about Windsor

Windsor B&B information

Number of reviews	1,178
Accommodation	15 B&B
Lowest Price	฿5,128
Highest Price	฿8,998

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.

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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