Windsor B&B: Find the Best Bed and Breakfast from CA $214

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 downtown core. 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

CA $273 total

includes taxes & fees

Sep 1 - Sep 2

2. The Vesper

Woodstock

Keith

CA $268 total

includes taxes & fees

Aug 31 - Sep 1

3. Sleep Woodstock - Dog Friendly King Suite

Woodstock

David M.

CA $226 total

includes taxes & fees

Sep 14 - Sep 15

4. Deer Brook Inn

Woodstock

Laurence

CA $346 total

includes taxes & fees

Sep 13 - Sep 14

5. Echo Lake Inn

Plymouth

Michael

CA $318 total

includes taxes & fees

Aug 31 - Sep 1

6. Stay At Jimmy's

Woodstock

Jeanne

CA $534 total

includes taxes & fees

Sep 10 - Sep 11

7. Stone Hearth Inn and Eatery

Chester

Olena

CA $263 total

includes taxes & fees

Aug 31 - Sep 1

8. Harvest Barn Inn

Bellows Falls

Michael

CA $237 total

includes taxes & fees

Sep 1 - Sep 2

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Top Windsor Hotel Reviews

Align Inn Vermont

10/10 Excellent

"First night of three, great room, very comfortable. Went to get coffee, came back, key worked. Went for awesome breakfast provided, key didn't work. Even desk master card didn't work. They were going to change the battery so we went exploring. Got back, still not working so were moved to another room which I will absolutely request next time we go there! Highly recommend, can't wait to see the wellness spa retreat portion which is still in development. Staff very accommodating and friendly. Pizza Chef next door with cute miniature golf course!! Probably best pizza we've had in a very long time. Do not hesitate to book here!"

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	1,271
Accommodation	38 B&B
Lowest Price	CA $214
Highest Price	CA $754

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. 12 mi (19.3 km) from the downtown core. Deer Brook Inn: 5 rooms. Located 13.4 mi (21.6 km) from the core 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 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 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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