Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 23 B&B in Windsor with updated reviews, rates, and availability.

Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (328)
"Lots of charm and very clean. "
The price is AED 807
AED 976 total
includes taxes & fees
17 Mar - 18 Mar
Snowed Inn
The Vesper
Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is AED 517
AED 568 total
includes taxes & fees
25 Feb - 26 Feb
The Vesper
The Jackson
Exterior

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (204)
"Very comfortable accommodations, and incredibly friendly and helpful staff. It was great to have coffee/tea available anytime and we spent lots of time by the cozy fire. "
The price is AED 820
AED 902 total
includes taxes & fees
2 Mar - 3 Mar
The Jackson
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (83)
"Charming historic inn with incredibly good breakfast and dinner menu. Bakery also out of this world. Kids loved the library:game room and 24hr hot cocoa bar. Family owned- mother tubs inn and her children run the restaurant. Such a warm, lovely family. If you have trouble with stairs, may not be the best for you, but otherwise would stay again."
The price is AED 1,218
AED 1,327 total
includes taxes & fees
24 Feb - 25 Feb
Stone Hearth Inn and Eatery
The Buckmaster Inn
Property entrance

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"I had a great stay at the Buckmaster Inn for ski weekend at Okemo. The house is beautiful with many classic colonial touches throughout. Best of all, Richard and Elizabeth are gracious hosts who go above and beyond to make their guests comfortable. It snowed the last night of my stay and Richard got up extra early to clear the driveway and my car! I will be back whenever I can visit. "
The Buckmaster Inn
Mountain Valley Retreat
Property grounds

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (164)
"Mike and Barbara were charming hosts. Their place was very quaint and inviting. And Mike made a delicious breakfast!! "
The price is AED 404
AED 457 total
includes taxes & fees
27 Feb - 28 Feb
Mountain Valley Retreat
Echo Lake Inn
Front of property

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is AED 942
AED 1,027 total
includes taxes & fees
25 Mar - 26 Mar
Echo Lake Inn
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (205)
"We had a wonderful weekend stay at the Inn! The 3 course breakfast was fantastic, the bed was comfortable, the shower was amazing, and the space was homey and cute. We would absolutely stay again!"
The price is AED 579
AED 631 total
includes taxes & fees
26 Feb - 27 Feb
Harvest Barn Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (28)
"We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was...
The price is AED 915
AED 1,006 total
includes taxes & fees
23 Feb - 24 Feb
Stay At Jimmy's
Dexter's Inn
Front of property

Dexter's Inn

3.0 star property
8.6 out of 10, Excellent, (68)
"Amazing place to stay for our Girl Scout ski trip! We rented the cottage which sleeps 12 and had two large, comfy rooms for adults plus large family room and new built in beds off family room for the girls. Well appointed modernized rooms while still retaining an authentic Inn feeling. Everyone enjoyed the breakfast buffet, especially the French Toast. We explored the grounds after breakfast and the girls enjoyed being unplugged and interacting with nature. Overall a wonderful experience and our...
The price is AED 909
AED 986 total
includes taxes & fees
23 Feb - 24 Feb
Dexter's Inn
Golden Stage Inn B&B
Front of property

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Family run B&B close to Okemo. Wonderful hosts. "
Golden Stage Inn B&B
King & Queen Suite in Historic Inn Circa 1780
Room

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"This is a fine place to stay. Everything is thoughtfully provided to make guests comfortable. The bed was very high quality, too. There were snacks, breakfast options, and good coffee available in the morning. Nothing fancy, but very useful and much appreciated."
The price is AED 400
AED 687 total
includes taxes & fees
23 Mar - 24 Mar
King & Queen Suite in Historic Inn Circa 1780
Room in Historic Inn! 20 Minutes to Okemo!
Room

Room in Historic Inn! 20 Minutes to Okemo!

9.4 out of 10, Exceptional, (13)
"I loved the room we stayed in. It was such a comfortable bed as well as the pillows. The bathroom was large and just about everything in our room was like a storybook. Loved skimming through some of the old books...so informative. The only thing I wished we knew is it was difficult to find a place to eat as we were there Monday thru Wednesday morning and no eateries on Main Street was opened. We drove a half our to eat breakfast. Perhaps it was the wrong season to go but the foliage was...
The price is AED 400
AED 654 total
includes taxes & fees
16 Mar - 17 Mar
Room in Historic Inn! 20 Minutes to Okemo!
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Living area

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"I was enchanted to be staying in a beautiful antique decorated place. And the jacuzzi tub was large, comfortable, and easily accessed by a step."
The price is AED 400
AED 654 total
includes taxes & fees
16 Mar - 17 Mar
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Room

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 AED 290
AED 551 total
includes taxes & fees
2 Mar - 3 Mar
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
The Woodstocker B&B
Front of property

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (51)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
The Woodstocker B&B
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"Darling -- Wonderful location, hosts and great breakfast -- We will be back during ski season. Thank you. "
Woodbridge Inn
Windsor Mansion Inn
Exterior

Windsor Mansion Inn

3.5 star property
9.2 out of 10, Wonderful, (289)
"We had a lovely time at the Windsor Mansion Inn over New Years! Andy was incredible accommodating and friendly to make our group feel right at home. The beds were very comfortable the the rooms were spacious. The mansion is gorgeous. Yummy breakfast too. We hope to stay again!"
Windsor Mansion Inn
Deer Brook Inn
Property entrance

Deer Brook Inn

4.0 star property
10.0 out of 10, Exceptional, (21)
"The Inn was so lovely and charming and exceeded our expectations! The hospitality offered by the Inn Keeper and his team was truly remarkable and we felt welcome and spoiled throughout our stay. The property itself is stunning and the attention to detail is five star in our book!!! We will definitely be back! Plan your stay!! You won’t be disappointed!!"
Deer Brook Inn
Inn at Water's Edge
Front of property

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.2 out of 10, Wonderful, (66)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is AED 294
AED 1,022 total
includes taxes & fees
24 Feb - 25 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

9.2 out of 10, Wonderful, (27)
"Very clean, thankful for NO smoke smell. Very close to Okeemo summit. Would stay again. "
The price is AED 242
AED 680 total
includes taxes & fees
2 Mar - 3 Mar
Efficient condo near slopes with kitchenette & great location
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.

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 Mt Ascutney State Park 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. Situated 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 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, Mt Ascutney State Park and Connecticut River 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.