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. 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

Yanil

HK$2,796 total

includes taxes & fees

20 Sept - 21 Sept

2. Echo Lake Inn

Plymouth

Michael

HK$2,806 total

includes taxes & fees

13 Oct - 14 Oct

3. Snowed Inn

Killington

Brendan

HK$1,215 total

includes taxes & fees

20 Sept - 21 Sept

4. The Vesper

Woodstock

Keith

HK$2,967 total

includes taxes & fees

20 Sept - 21 Sept

5. Stone Hearth Inn and Eatery

Chester

John

HK$1,786 total

includes taxes & fees

23 Sept - 24 Sept

6. Stay At Jimmy's

Woodstock

Jeanne

HK$3,444 total

includes taxes & fees

27 Sept - 28 Sept

7. Harvest Barn Inn

Bellows Falls

Michael

HK$1,584 total

includes taxes & fees

23 Sept - 24 Sept

8. Deer Brook Inn

Woodstock

Laurence

HK$3,716 total

includes taxes & fees

29 Sept - 30 Sept

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Top Windsor Hotel Reviews

The Jackson

10/10 Excellent

"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"

Woodstock Inn & Resort

8/10 Good

"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."

Hotel Coolidge

8/10 Good

"This is a very old hotel on the national historic record. Because of that the doors and floors creak and the floors slope. The bathroom has older fixtures but work fine. Our room was actually two rooms; one with a queen bed and one with a small couch and sink. Both rooms had TVs. We had a small fridge. Bed was comfortable. They had an elevator that was very slow but since we had heavy items we were very grateful for it. The stairway and moldings were beautiful. If you enjoy historic architecture you will appreciate this hotel. The parking seemed a bit sketchy but was actually fine. They had a fireplace and a Keurig in lobby so tea, coffee and hot chocolate available 24/7. Also had vouchers for discounts at neighboring breakfast sites. They are dog friendly, but only for specified rooms. They also had a refundable $100 charge for any damage done due to the dog. There was a $25 charge for the dog which is pretty standard. All in all it was a fine place to stay."

Find out more about Windsor

Windsor B&B information

Number of reviews	1,372
Accommodation	38 B&B
Lowest Price	HK$1,215
Highest Price	HK$4,271

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. 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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