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. 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

฿6,520 total

includes taxes & fees

31 Aug - 1 Sept

2. The Vesper

Woodstock

Keith

฿6,374 total

includes taxes & fees

7 Sept - 8 Sept

3. Deer Brook Inn

Woodstock

Laurence

฿8,474 total

includes taxes & fees

31 Aug - 1 Sept

4. Echo Lake Inn

Plymouth

Michael

฿8,319 total

includes taxes & fees

1 Sept - 2 Sept

5. Stay At Jimmy's

Woodstock

Jeanne

฿12,711 total

includes taxes & fees

10 Sept - 11 Sept

6. Stone Hearth Inn and Eatery

Chester

Olena

฿7,539 total

includes taxes & fees

31 Aug - 1 Sept

7. Harvest Barn Inn

Bellows Falls

Michael

฿6,276 total

includes taxes & fees

31 Aug - 1 Sept

8. Snowed Inn

Killington

James

฿5,088 total

includes taxes & fees

31 Aug - 1 Sept

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Top Windsor Hotel Reviews

The Mountain Inn at Killington

10/10 Excellent

"We loved this hotel. We were here in the summer, so we enjoyed the outdoor seating and the outdoor heated pool, plus very close distance to Killington Adventure Center (could have walked but we chose to drive). The game room was great for our teenagers, with a full pool table and board games. The staff was extremely friendly and knowledgable of the area, and gave suggestions for nearby restauarants and hikes. The upstairs has a large indoor lounge area to relax outside your hotel room with friends, which I can see being awesome after a day of skiing."

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."

Hotel Coolidge

10/10 Excellent

"Definitely go expecting simplicity and historical ambiance, if you go expecting luxury, you will be disappointed. The hotel offers a reasonable price, walking distance to many restaurants and places to shop. The train station does NOT in fact shake the hotel as mentioned in other reviews. Staff is accommodating and friendly."

The Shire Woodstock

8/10 Good

"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."

Super 8 by Wyndham White River Junction

8/10 Good

"Friendly, helpful, staff and a comfortable room with a nice view. Facility needs some maintenance. Walls were chipped, sink did not drain well, and shower was difficult to operate. Walking up to the second level without an elevator with a suitcase was okay for me. But, unlikely for mobility impaired people."

Find out more about Windsor

Windsor B&B information

Number of reviews	688
Accommodation	16 B&B
Lowest Price	฿5,088
Highest Price	฿18,029

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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