Photo by William E Berry Jr.

Bed and Breakfast in Windsor

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured B&B in Windsor

Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (223)
"A refurbished old Vermont home with a beautiful view of the Connecticut river. The young couple who own the home were delightful and very attentive. It was comfortable and very unique. I would certainly stay here again."
Harvest Barn Inn
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is NZ$279
includes taxes & fees
1 Sept - 2 Sept
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (16)
"My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again."
The price is NZ$260
includes taxes & fees
24 Aug - 25 Aug
Room in Historic Inn! 20 Minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (15)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is NZ$380
includes taxes & fees
24 Aug - 25 Aug
King & Queen Suite in Historic Inn Circa 1780
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Dining

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 NZ$352
includes taxes & fees
17 Aug - 18 Aug
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, (39)
"Superb stay in all ways!"
The price is NZ$458
includes taxes & fees
26 Aug - 27 Aug
Stay At Jimmy's
The Vesper
Economy Room

The Vesper

3.0 star property
9.4 out of 10, Exceptional, (27)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is NZ$311
includes taxes & fees
20 Aug - 21 Aug
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, (92)
"Sweet place to stay"
The price is NZ$367
includes taxes & fees
27 Aug - 28 Aug
Stone Hearth Inn and Eatery
The Jackson
Front of property

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (225)
"Great stay! "
The Jackson
Echo Lake Inn
Outdoor pool

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 NZ$412
includes taxes & fees
19 Aug - 20 Aug
Echo Lake Inn
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (357)
"Beautiful place to stay! 10/10 would recommend. You're going to love it!"
The price is NZ$312
includes taxes & fees
18 Aug - 19 Aug
Snowed Inn
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (182)
"Great experience. Very accommodating! Room was great! Everything was clean and homemade breakfast was amazing. Thanks "
The price is NZ$208
includes taxes & fees
18 Aug - 19 Aug
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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Top Windsor Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"This is a renovated old-fashioned motel. Nice people, clean, good breakfast, cool pub/restaurant to walk to next door. "
David 1-night trip
Posted 15 hours ago
Align Inn Vermont

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 Path of Life Garden 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?
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 decor and library. The Jackson: 11 rooms. 12.2 mi (19.7 km) from the city centre. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 12 mi (19.3 km) from the city centre. Stay At Jimmy's: 3 rooms. Located 11.9 mi (19.1 km) from the core of Windsor. Enjoy the Jetted bath and private garden.
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, Connecticut River and Path of Life Garden are some notable spots. You should put Harpoon Brewery and Mt Ascutney State Park 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.