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. 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

1. The Jackson

West Woodstock

Brian

includes taxes & fees

9 Aug - 10 Aug

2. The Vesper

Woodstock

Terry

includes taxes & fees

18 Aug - 19 Aug

3. Stay At Jimmy's

Woodstock

Heather

includes taxes & fees

11 Aug - 12 Aug

4. Echo Lake Inn

Plymouth

Danielle

includes taxes & fees

10 Aug - 11 Aug

5. Deer Brook Inn

Woodstock

Sara

includes taxes & fees

9 Aug - 10 Aug

6. Stone Hearth Inn and Eatery

Chester

Kathleen

includes taxes & fees

12 Aug - 13 Aug

7. Harvest Barn Inn

Bellows Falls

Natalie

includes taxes & fees

18 Aug - 19 Aug

8. Snowed Inn

Killington

Rouslan

includes taxes & fees

12 Aug - 13 Aug

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Top Windsor Hotel Reviews

Holiday Inn Express Hotel & Suites White River Junction by IHG

10/10 Excellent

"We enjoyed the suite, it was a surprise that we didn’t expect. The doors to the underground parking garage were locked we couldn’t access the elevator. We thoroughly enjoyed the wonderful breakfast, didn’t expect it to be a hot breakfast with so many options, that was awesome! Finally, loved the decaffeinated coffee, fresh ground while you wait that was another unexpected surprise that was awesome as well!! Thank you very much!"

Mountain Meadows Lodge

10/10 Excellent

"We loved our stay at Mountain Meadows Lodge. It is a beautiful and peaceful place with many amenities on site, like kayaks, board games and s’mores in the evening. Most importantly it has Victoria and Mike, whose hospitality can’t be beat. They cook a great breakfast, have lots of advice about the local area, and make everyone feel like family. They were also a big help when we had a problem with our onward travel."

Hanover Inn Dartmouth

10/10 Excellent

"Beautiful, well maintained historic hotel. Turn down service. They sent someone to make up the pullout in our room. This spot is one of the only nice hotels in the area, far surpasses the Marriott’s and Hilton’s on the highway, and a certain lakeside resort nearby that charges double should be skipped at all costs."

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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 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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