Photo by William E Berry Jr.

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Jun 27 - Jun 29
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Jul 4 - Jul 6
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Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

B&B in Windsor

Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (217)
"Very accommodating and wonderful people! Hoping to return!"
Harvest Barn Inn
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Terrace/patio

Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature

10.0 out of 10, Exceptional, (1)
"A warm and inviting host and a cute cozy space to spend a few days. Nice big bedrooms with a fireplace our host supplied wood and we were able to enjoy that. Great location for visiting our son at Dartmouth really close to Woodstock and Quechee!Great stay!"
The price is ￥28,568
￥44,744 total
includes taxes & fees
Jun 18 - Jun 19
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is ￥17,144
￥28,883 total
includes taxes & fees
Jun 17 - Jun 18
King & Queen Suite in Historic Inn Circa 1780
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (15)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
The price is ￥14,263
￥24,042 total
includes taxes & fees
Jun 17 - Jun 18
Room in Historic Inn! 20 Minutes to Okemo!
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Interior

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

8.0 out of 10, Very Good, (1)
"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 ￥14,263
￥24,849 total
includes taxes & fees
Jun 17 - Jun 18
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (31)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is ￥28,670
￥31,537 total
includes taxes & fees
Jun 17 - Jun 18
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, (20)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is ￥25,212
￥27,734 total
includes taxes & fees
Jun 18 - Jun 19
The Vesper
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (90)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is ￥26,762
￥29,171 total
includes taxes & fees
Jul 7 - Jul 8
Stone Hearth Inn and Eatery
The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (216)
"What a lovely place to stay. The couple that manage The Jackson are absolutely wonderful and made our stay fabulous. I would highly recommend staying here with gorgeous surroundings, charming rooms and lovely hospitality."
The Jackson
Echo Lake Inn
Exterior

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 ￥28,890
￥31,490 total
includes taxes & fees
Jun 18 - Jun 19
Echo Lake Inn
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (350)
"Such a beautiful and cozy place to stay!! Welcoming atmosphere and people! Had a wonderful time!"
The price is ￥18,873
￥22,836 total
includes taxes & fees
Jun 17 - Jun 18
Snowed Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (177)
"Beautiful scenery. Accommodating hosts, helpful to move my luggage up and down staircase, even putting into my car when I departed. Excellent made to order breakfast, multiple decaf coffee refills, even preparing a to go coffee in my travel cup. I would definitely stay again when visiting this region. A gem."
The price is ￥15,848
￥17,908 total
includes taxes & fees
Jun 17 - Jun 18
Mountain Valley Retreat
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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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. Stay At Jimmy’s: 3 rooms. Located 11.9 mi (19.1 km) from the core of Windsor. Enjoy the jetted tubs and private yard.
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 American Precision Museum and Harpoon Brewery 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.