Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
Oct 17 - Oct 19
In two weeks
Oct 24 - Oct 26
In one month
Nov 7 - Nov 9
In two months
Dec 5 - Dec 7

B&B in Windsor

Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (238)
"Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! "
Harvest Barn Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (184)
"Absolutely lovely stay!"
The price is ￥16,631
￥18,793 total
includes taxes & fees
Oct 27 - Oct 28
Mountain Valley Retreat
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (236)
"Excellent Vintage style B&B. "
The Jackson
The Vesper
Economy Room | 1 bedroom, individually decorated, individually furnished, free WiFi

The Vesper

3.0 star property
9.0 out of 10, Wonderful, (36)
"Adorable home and room. Very clean. Great location. Loved our stay! "
The price is ￥26,506
￥29,156 total
includes taxes & fees
Nov 3 - Nov 4
The Vesper
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (44)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
The price is ￥37,646
￥41,411 total
includes taxes & fees
Nov 3 - Nov 4
Stay At Jimmy's
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (16)
"My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again."
The price is ￥14,968
￥25,231 total
includes taxes & fees
Nov 3 - Nov 4
Room in Historic Inn! 20 Minutes to Okemo!
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (99)
"Good breakfast and dinner options. Great location for hiking."
The price is ￥42,214
￥46,013 total
includes taxes & fees
Oct 13 - Oct 14
Stone Hearth Inn and Eatery
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Dining

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is ￥13,456
￥24,384 total
includes taxes & fees
Nov 3 - Nov 4
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (364)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
The price is ￥43,392
￥52,504 total
includes taxes & fees
Oct 15 - Oct 16
Snowed Inn
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (66)
"Staff was very friendly and welcoming "
The price is ￥77,777
￥85,554 total
includes taxes & fees
Oct 14 - Oct 15
Woodbridge Inn
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.8 out of 10, Exceptional, (16)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is ￥21,015
￥34,374 total
includes taxes & fees
Nov 10 - Nov 11
King & Queen Suite in Historic Inn Circa 1780
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is ￥24,039
￥36,576 total
includes taxes & fees
Oct 19 - Oct 20
Honeymoon Suite with Jacuzzi Tub in Historic 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

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"Great place to stay. Lovely atmosphere. Pool and hot tub were nice. Great hot buffet breakfast. They kept replenishing the hot food which was great. Room was clean. "
Lauren 1-night trip
Posted 20 hours ago
Fireside Inn & Suites West Lebanon

Find out more about Windsor

Windsor B&B information

Number of reviews
1,293
Accommodation
24 B&B
Lowest Price
￥18,793
Highest Price
￥85,554

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 Path of Life Garden and Paradise Park.
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: Windsor Mansion Inn: 17 rooms. 0.9 mi (1.4 km) from the heart of Windsor. Enjoy the unique décor and library. The Jackson: 11 rooms. 12.2 mi (19.7 km) from the downtown core. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 12 mi (19.3 km) from the heart of downtown.
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 Path of Life Garden 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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