Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 26 B&B in Windsor with updated reviews, rates, and availability.

The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (212)
"The hotel is great, the rooms are large and comfortable, the steep stairs are not for the faint hearted. "
The price is SAR 837
SAR 921 total
includes taxes & fees
18 May - 19 May
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (346)
"Such a beautiful and cozy place to stay!! Welcoming atmosphere and people! Had a wonderful time!"
The price is SAR 641
SAR 776 total
includes taxes & fees
25 May - 26 May
Snowed Inn
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.8 out of 10, Exceptional, (17)
"Lovely, immaculate room - breakfast delish ! highly recommend this charming boutique hotel !"
The price is SAR 469
SAR 516 total
includes taxes & fees
3 May - 4 May
The Vesper
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (173)
"Great hosts and location. "
The price is SAR 413
SAR 466 total
includes taxes & fees
4 May - 5 May
Mountain Valley Retreat
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (29)
"Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return."
The price is SAR 1,121
SAR 1,233 total
includes taxes & fees
4 May - 5 May
Stay At Jimmy's
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (210)
"Nice and comfortable great breakfast"
The price is SAR 755
SAR 823 total
includes taxes & fees
9 May - 10 May
Harvest Barn Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (89)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is SAR 1,243
SAR 1,355 total
includes taxes & fees
5 May - 6 May
Stone Hearth Inn and Eatery
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is SAR 726
SAR 791 total
includes taxes & fees
2 Jun - 3 Jun
Echo Lake 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 SAR 484
SAR 760 total
includes taxes & fees
5 May - 6 May
Honeymoon Suite with Jacuzzi Tub in Historic Inn
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"Very charming B&B with amazing hosts!"
The Buckmaster Inn
Dexter's Inn
Game room

Dexter's Inn

3.0 star property
8.8 out of 10, Excellent, (70)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
The price is SAR 742
SAR 805 total
includes taxes & fees
3 May - 4 May
Dexter's Inn
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Interior

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 334
SAR 605 total
includes taxes & fees
14 May - 15 May
Historic Chester Inn! Circa, 1870 - right on Main Street & 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, (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 446
SAR 752 total
includes taxes & fees
9 May - 10 May
King & Queen Suite in Historic Inn Circa 1780
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

Room in Historic Inn! 20 Minutes to Okemo!

9.4 out of 10, Exceptional, (13)
"Our stay was outstanding. The room was spacious, comfy and clean. The Inn was very quiet during our stay. We made friends with the local chipmunk who is extremely tame. We love having a place so cozy to stay when we are in the area. "
The price is SAR 450
SAR 718 total
includes taxes & fees
8 May - 9 May
Room in Historic Inn! 20 Minutes to Okemo!
Golden Stage Inn B&B
Seasonal outdoor pool

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Very beautiful place and excellent service "
Golden Stage Inn B&B
Woodbridge Inn
Front of property - evening/night

Woodbridge Inn

3.0 star property
9.6 out of 10, Exceptional, (64)
"It was a lovely, comfortable property and the hosts couldn’t have been more hospitable. Great breakfast and great company. "
Woodbridge Inn
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 price is SAR 1,796
SAR 2,134 total
includes taxes & fees
23 May - 24 May
The Woodstocker B&B
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Terrace/patio

Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature

The price is SAR 661
SAR 1,064 total
includes taxes & fees
6 May - 7 May
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Windsor Mansion 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
Rockledge Farm country living
Exterior

Rockledge Farm country living

9.8 out of 10, Exceptional, (29)
"Beautiful property and lovely people! We very much enjoyed our stay and the breakfast provided was an added bonus! :)"
Rockledge Farm country living
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
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Crescent Cottage
Terrace/patio

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"We had a wonderful long weekend stay at the cottage on Crescent Lake! The place has all of the amenities that you need for a relaxing and fun filled time on the lake. We will definitely be back for another stay next year!"
Cozy Crescent Cottage
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is SAR 638
SAR 1,373 total
includes taxes & fees
5 May - 6 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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 Paradise Park and Path of Life Garden.
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. 12.2 mi (19.7 km) from the downtown core. Enjoy the designer toiletries and library. The Vesper: 9 rooms. Situated 12 mi (19.3 km) from the heart of Windsor.
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, Connecticut River and Paradise Park 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.