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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sep - 7 Sep
In one month
19 Sep - 21 Sep
In two months
17 Oct - 19 Oct

Browse Select Windsor B&B

Our top choices for Windsor bed & breakfast

Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (182)
"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "
The price is ฿3,582
฿4,048 total
includes taxes & fees
1 Sept - 2 Sept
Mountain Valley Retreat
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
Harvest Barn Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (39)
"Superb stay in all ways!"
The price is ฿6,500
฿7,150 total
includes taxes & fees
28 Aug - 29 Aug
Stay At Jimmy's
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (28)
"Easy check in. Friendly staff. Bed was comfortable. Walkable to downtown Woodstock. Breakfast was limited but good!"
The price is ฿5,512
฿6,063 total
includes taxes & fees
26 Aug - 27 Aug
The Vesper
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (227)
"Great stay! "
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (358)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
The price is ฿5,021
฿6,076 total
includes taxes & fees
1 Sept - 2 Sept
Snowed Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (93)
"Sweet place to stay"
The price is ฿6,560
฿7,150 total
includes taxes & fees
28 Aug - 29 Aug
Stone Hearth Inn and Eatery
Echo Lake Inn
Outdoor pool

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Charming place, the food was great, rooms clean, and service was excellent"
The price is ฿7,506
฿8,182 total
includes taxes & fees
2 Sept - 3 Sept
Echo Lake Inn
Woodbridge Inn
Front of property – evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Great place to stay"
The price is ฿14,406
฿15,847 total
includes taxes & fees
15 Sept - 16 Sept
Woodbridge 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

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"It is pricey any discounts if you are traveling for a Dr appointment at Dartmouth?"
Jason 1-night trip
Posted 3 days ago
Hilton Garden Inn Hanover Lebanon

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 Path of Life Garden and Paradise Park.
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: Windsor Mansion Inn: 17 rooms. 0.9 mi (1.4 km) from the heart of Windsor. Enjoy the unique decor and library. The Jackson: 11 rooms. 12.2 mi (19.7 km) from the city centre. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 12 mi (19.3 km) from the city centre. Stay At Jimmy's: 3 rooms. Located 11.9 mi (19.1 km) from the core of Windsor. Enjoy the Jetted bath and private garden.
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 Path of Life Garden 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.