A snow-covered river valley with a bridge and a town.

Bed and Breakfast in Windsor

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Check prices for these dates

Next weekend
25 Sept - 27 Sept
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Windsor bed & breakfast

Restaurant

1. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (318 reviews)
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
United States
Laura
The price is NZ$561
includes taxes & fees
21 Sept - 22 Sept
The Jackson
Interior

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (78 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is NZ$541
includes taxes & fees
21 Sept - 22 Sept
The Vesper
Front of property

3. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (125 reviews)
"Wonderful staff and restaurant"
United States
John
The price is NZ$398
includes taxes & fees
21 Sept - 22 Sept
Stone Hearth Inn and Eatery
Exterior

4. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (102 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
The price is NZ$587
includes taxes & fees
13 Oct - 14 Oct
Echo Lake Inn
Front of property – evening/night

5. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67 reviews)
"Great place to stay"
United States
eric
The price is NZ$952
includes taxes & fees
21 Sept - 22 Sept
Woodbridge Inn
Interior

6. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is NZ$803
includes taxes & fees
25 Sept - 26 Sept
Deer Brook Inn
Porch

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (281 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is NZ$335
includes taxes & fees
23 Sept - 24 Sept
Harvest Barn Inn
Front of property

8. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (52 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
The price is NZ$918
includes taxes & fees
21 Oct - 22 Oct
Stay At Jimmy's
Front of property

9. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (410 reviews)
"Great hot tub and breakfast."
United States
Brendan
The price is NZ$311
includes taxes & fees
18 Oct - 19 Oct
Snowed Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good
"Put ATM machine in lobby"
James 2-night trip
Posted 3 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton

Find out more about Windsor

Windsor B&B information

Number of reviews
1,373
Accommodation
38 B&B
Lowest Price
NZ$311
Highest Price
NZ$952

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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