Photo by William E Berry Jr.

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

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (188)
"Great people "
The price is SAR 791
SAR 871 total
includes taxes & fees
6 Jan - 7 January 2025
The Jackson

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (313)
"Great place and people. Hot tub was nice too. They had home cooked breakfast (took a little long) but great. Fully recommend"
The price is SAR 905
SAR 1,095 total
includes taxes & fees
20 Jan - 21 January 2025
Snowed Inn

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (12)
"Dana and her staff were so welcoming and our experience was nothing less than perfect. My husband and I travel for a living and I feel like The Vesper is a little hidden gem that we have discovered and we look forward to staying there again. Stephanie Louris Ps.. Breakfast was so delicious!!"
The price is SAR 528
SAR 581 total
includes taxes & fees
6 Jan - 7 January 2025
The Vesper

Mountain Valley Retreat

2.5 star property
9.8 out of 10, Exceptional, (156)
"Quiet charming home a few miles off the highway. Only 2 rooms and a very picturesque, relaxing setting. Will serve a home cooked full breakfast in the morning. "
The price is SAR 413
SAR 467 total
includes taxes & fees
13 Jan - 14 January 2025
Mountain Valley Retreat

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (75)
"Breakfast was great. The owner is super nice"
The price is SAR 840
SAR 916 total
includes taxes & fees
30 Dec - 31 Dec
Stone Hearth Inn and Eatery

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is SAR 930
SAR 1,014 total
includes taxes & fees
21 Jan - 22 January 2025
Echo Lake Inn

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (56)
"Elizabeth and Richard were absolutely wonderful hosts! I enjoyed every second of staying at this property. They went out of their way to be hospitable and to make all guests comfortable. The breakfast was fantastic each day and they had wonderful suggestions for the local area. I was already planning a trip back before I had even checked out. Highly recommend!!"
The Buckmaster Inn

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (197)
"No Complaints, Excellent breakfast "
The price is SAR 592
SAR 645 total
includes taxes & fees
8 Jan - 9 January 2025
Harvest Barn Inn

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (23)
"Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!"
The price is SAR 935
SAR 1,028 total
includes taxes & fees
2 Jan - 3 January 2025
Stay At Jimmy's

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 SAR 635
SAR 988 total
includes taxes & fees
6 Jan - 7 January 2025
King & Queen Suite in Historic Inn Circa 1780

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 SAR 799
SAR 867 total
includes taxes & fees
28 Dec - 29 Dec
Dexter's Inn

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 SAR 559
SAR 858 total
includes taxes & fees
6 Jan - 7 January 2025
Room in Historic Inn! 20 Minutes to Okemo!

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 SAR 597
SAR 904 total
includes taxes & fees
6 Jan - 7 January 2025
Honeymoon Suite with Jacuzzi Tub in Historic Inn

The Woodstocker B&B

4.0 star property
10.0 out of 10, Exceptional, (50)
"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

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

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 SAR 582
SAR 913 total
includes taxes & fees
6 Jan - 7 January 2025
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (22)
"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

Franklyn Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (17)
"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)
"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
9.6 out of 10, Exceptional, (17)
"The history of the house is provided. Beutiful house and grounds."
Snapdragon 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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST 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 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 Harpoon Brewery and American Precision Museum 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.