Photo by William E Berry Jr.

Find Windsor Bed And Breakfast

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Compare 24 B&B in Windsor with updated reviews, rates, and availability.

The Vesper
3.0 star property
8.0 out of 10, Very Good, 1 review
" Goof"
The price is ¥27,103
per night
Jun 17 - Jun 18
The Vesper
Mountain Valley Retreat
2.5 star property
9.6 out of 10, Exceptional, 134 reviews
"Mike is an excellent host with great attention to detail. Would highly recommend this spot for whatever occasion takes you to Killington area. "
The price is ¥17,150
per night
Jun 9 - Jun 10
Mountain Valley Retreat
Stone Hearth Inn and Eatery
2.0 star property
9.2 out of 10, Wonderful, 50 reviews
"My fiance and I had an amazing stay here. Vicki and her staff are incredible and attentive to their guests. The food is beyond amazing one of the best meals we have had. We highly recommend this cute and quaint spot and definitely will be making many trips back! "
The price is ¥36,100
per night
Jun 11 - Jun 12
Stone Hearth Inn and Eatery
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Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, 171 reviews
"I had a wonderful stay. Kaelan was an awesome host. great breakfast as well!"
The price is ¥26,359
per night
Jun 12 - Jun 13
Harvest Barn Inn
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, 2 reviews
"Great hosts and very comfortable room."
The price is ¥38,563
per night
Jun 12 - Jun 13
Stay At Jimmy's
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, 57 reviews
"Very nice experience. The people running the bed and breakfast were very nice "
Woodbridge Inn
Snowed Inn
3.5 star property
9.8 out of 10, Exceptional, 253 reviews
"The place is beautiful and the iwners are super friendly. The breakfast was delicious. Great place!"
The price is ¥20,381
per night
Jun 10 - Jun 11
Snowed Inn
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, 167 reviews
"Fantastic homemade breakfast and cookies at night. The rooms were very clean and comfortable. The staff was fantastic! Will be staying again. Book directly and save money."
The price is ¥42,704
per night
Jun 9 - Jun 10
The Jackson House Inn
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, 90 reviews
"Lovely inn. Went to VT to see the total eclipse "
The price is ¥31,732
per night
Jun 17 - Jun 18
Echo Lake Inn
Dexter's Inn
3.0 star property
8.6 out of 10, Excellent, 68 reviews
"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...
Dexter's Inn
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, 50 reviews
"it was the most charming, cleanest, best breakfast we've ever had going to b&bs 6-12 times a year for over 20 years. it looked like the kind you see in magazines but never in real life."
The Buckmaster Inn
Golden Stage Inn B&B
3.5 star property
10.0 out of 10, Exceptional, 22 reviews
"We chose this bed and breakfast based on others’ reviews- and you should, too! Our room was lovely and homey and had everything you’d want or need available. Mike and Julie are spectacularly thoughtful hosts. We felt welcomed, cared for, and a little bit spoiled :) during our three day stay. Will absolutely stay here again on our next visit to VT! "
Golden Stage Inn B&B
King & Queen Suite in Historic Inn Circa 1780
9.6 out of 10, Exceptional, 13 reviews
"SUCH a lovely, cozy stay in this beautiful VT town. Could not recommend more highly!"
The price is ¥43,209
per night
Jun 11 - Jun 12
King & Queen Suite in Historic Inn Circa 1780
Room in Historic Inn! 20 Minutes to Okemo!
9.0 out of 10, Wonderful, 10 reviews
"At first it was difficult to get in touch with the owners, as the number listed on some sights is the older number. Once I did they were wonderful. They took their time to think of everything to make your stay comfortable. So many little details! The town is so lovely - old victorian style and the house is walkable to a few restaurants. Great to have a mini kitchen available to use, with a big fridge to store items, while also a mini fridge in the room. Look forward to staying here again next...
The price is ¥18,584
per night
Jun 11 - Jun 12
Room in Historic Inn! 20 Minutes to Okemo!
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.0 out of 10, Very Good, 5 reviews
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
The price is ¥37,014
per night
Jun 11 - Jun 12
Honeymoon Suite with Jacuzzi Tub in Historic Inn
The Woodstocker B&B
4.0 star property
10.0 out of 10, Exceptional, 50 reviews
"This is a lovely and charming guest house / B&B, run by a very nice and friendly couple. During our stay they recommended a number of places to visit and were warm and welcoming every day. I would not hesitate to book with them again."
The Woodstocker B&B
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
The price is ¥13,938
per night
Jun 12 - Jun 13
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Franklyn Farm Inn
3.5 star property
9.8 out of 10, Exceptional, 17 reviews
"We had a lovely stay as a couple for 2 nights. All of the staff were very welcoming and the breakfast was always served fresh and hot. We enjoyed conversing with other guests over the breakfast and the individual German pancakes served on the first morning were scrumptious! "
Franklyn Farm Inn
Windsor Mansion Inn
3.5 star property
9.2 out of 10, Wonderful, 289 reviews
"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
Snapdragon Inn
3.5 star property
9.4 out of 10, Exceptional, 17 reviews
"The history of the house is provided. Beutiful house and grounds."
Snapdragon Inn
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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.

Other property types in Windsor

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, 30 reviews
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 32 reviews
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, 157 reviews
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
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.

Windsor B&B information

Number of reviews
1,428
Accommodation
24 B&B
Lowest Price
¥13,938
Highest Price
¥43,209

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 B&Bs to check out in Windsor: Windsor Mansion Inn: 17 rooms. Enjoy the unique décor and library. Snapdragon Inn: 4 rooms.
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.

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