Photo by William E Berry Jr.

Bed and Breakfast in Windsor

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Featured B&B in Windsor

Fireplace
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, (167)
"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 NZ$474
includes taxes & fees
26 May - 27 May
The Jackson House Inn
Exterior
Mountain Valley Retreat
2.5 star property
9.6 out of 10, Exceptional, (133)
"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 NZ$198
includes taxes & fees
6 Jun - 7 Jun
Mountain Valley Retreat
Economy Room
The Vesper
3.0 star property
8.0 out of 10, Very good, (1)
" Goof"
The price is NZ$233
includes taxes & fees
27 May - 28 May
The Vesper
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Porch
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (170)
"Excellent B&B! Very cozy and friendly, gourmet breakfasts. And the town is very cool and artsy, good coffee shops. "
The price is NZ$304
includes taxes & fees
26 May - 27 May
Harvest Barn Inn
Front of property
Stone Hearth Inn and Eatery
2.0 star property
9.2 out of 10, Wonderful, (49)
"Such a great little Inn here in Vermont. "
The price is NZ$416
includes taxes & fees
28 May - 29 May
Stone Hearth Inn and Eatery
Front of property - evening/night
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, (57)
"Very nice experience. The people running the bed and breakfast were very nice "
Woodbridge Inn
Front of property
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (1)
"Our short but sweet stay was great. Check in was smooth and the breakfast bundles were a nice touch. The rooms are newly designed and felt like such a getaway!"
The price is NZ$449
includes taxes & fees
26 May - 27 May
Stay At Jimmy's
Exterior
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (90)
"Lovely inn. Went to VT to see the total eclipse "
The price is NZ$363
includes taxes & fees
4 Jun - 5 Jun
Echo Lake Inn
Game room
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...
Dexter's Inn
Seasonal outdoor pool
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
Exterior
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, (49)
"This Inn was built in 1801, so it’s a very old Inn. There are not enough superlatives. Fantastic. Awesome. Amazing. Going back definitely. All rooms are beautifully furnished with four-posters and very comfortable chairs. Place to be lived in. Immaculately clean. As soon as you walk in you want to stay forever. Warm. Delicious homemade breakfasts. Innkeeper Elizabeth is friendly and accommodating. We could have talked for hours. Still blissing out days later. "
The Buckmaster Inn
Outdoor spa tub
Snowed Inn
3.5 star property
9.8 out of 10, Exceptional, (252)
"The place is beautiful and the iwners are super friendly. The breakfast was delicious. Great place!"
The price is NZ$261
includes taxes & fees
26 May - 27 May
Snowed Inn
Interior
King & Queen Suite in Historic Inn Circa 1780
9.6 out of 10, Exceptional, (13)
"SUCH a lovely, cozy stay in this beautiful VT town. Could not recommend more highly!"
The price is NZ$645
includes taxes & fees
28 May - 29 May
King & Queen Suite in Historic Inn Circa 1780
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!
9.0 out of 10, Wonderful, (10)
"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 NZ$305
includes taxes & fees
1 Jun - 2 Jun
Room in Historic Inn! 20 Minutes to Okemo!
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.0 out of 10, Very good, (5)
"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 NZ$545
includes taxes & fees
27 May - 28 May
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Front of property
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 price is NZ$552
includes taxes & fees
26 May - 27 May
The Woodstocker B&B
Interior
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
The price is NZ$257
includes taxes & fees
27 May - 28 May
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Courtyard
Franklyn Farm Inn
3.5 star property
9.8 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
Front of property - evening/night
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
Iron/ironing board, free WiFi
Snapdragon Inn
3.5 star property
9.4 out of 10, Exceptional, (17)
"The history of the house is provided. Beutiful house and grounds."
Snapdragon Inn
Don't see what you're looking for?
See all available properties in Windsor
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

Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"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
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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
1,424
Accommodation
24 B&B
Lowest Price
NZ$198
Highest Price
NZ$645

Frequently asked questions

Searching for B&Bs in Windsor?
If you’re interested in something a little different than the traditional hotel experience, a stay at a bed and breakfast could be the perfect alternative for your trip. While you’re here, you can get to know Windsor by exploring its natural beauty—consider stopping at Mt Ascutney State Park and Paradise Park.
Are you considering apartments over traditional hotel rooms?
With attentive service, an atmosphere suited to mingling with other guests and tasty breakfasts, B&Bs provide a truly one-of-a-kind environment.
What are the best bed and breakfasts in Windsor?
Why not look at these B&Bs in Windsor: Windsor Mansion Inn: 17 rooms. Enjoy the unique decor and library. Snapdragon Inn: 4 rooms.
When is the best time to book my B&B in Windsor?
When you’re planning your getaway to Windsor, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm 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 should 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 map out your trip 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) away from the heart of the city. 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 explore more sights.

Recent Reviews in Windsor
Expedia verified reviews