Photo by William E Berry Jr.

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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

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, (206)
"Great staff and services. Rooms and toilets are a bit small. "
The price is SAR 744
SAR 819 total
includes taxes & fees
20 Mar - 21 Mar
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (333)
"Very nice Inn. Efficient and well run, the owners know what they are doing. Breakfast ordered ahead of time and a hot tub sign out means no hurry up and wait. "
The price is SAR 641
SAR 776 total
includes taxes & fees
3 Apr - 4 Apr
Snowed Inn
The Vesper
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"I loved that this property was within walking distance to all the shops and restaurants in downtown Woodstock "
The price is SAR 486
SAR 535 total
includes taxes & fees
7 Apr - 8 Apr
The Vesper
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (169)
"Mike and Barb we so incredibly accommodating and kind, I had a wonderful time staying here and would highly recommend it to others!"
The price is SAR 413
SAR 466 total
includes taxes & fees
24 Mar - 25 Mar
Mountain Valley Retreat
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (28)
"We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was...
The price is SAR 746
SAR 821 total
includes taxes & fees
20 Mar - 21 Mar
Stay At Jimmy's
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (208)
"We had a wonderful weekend stay at the Inn! The 3 course breakfast was fantastic, the bed was comfortable, the shower was amazing, and the space was homey and cute. We would absolutely stay again!"
The price is SAR 591
SAR 644 total
includes taxes & fees
25 Mar - 26 Mar
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, (87)
"The Inn was lovely. My grandchildren were welcomed with open arms ages 8 and 10. They loved our stay and asked for us to take them back. Breakfast specials were delicious and the attached restaurant was as well. We’ll be back!!"
The price is SAR 1,244
SAR 1,355 total
includes taxes & fees
20 Mar - 21 Mar
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 984
SAR 1,072 total
includes taxes & fees
7 Apr - 8 Apr
Echo Lake Inn
Dexter's Inn
Game room

Dexter's Inn

3.0 star property
8.8 out of 10, Excellent, (69)
"A cozy B&B just as expected "
The price is SAR 697
SAR 756 total
includes taxes & fees
27 Mar - 28 Mar
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 319
SAR 588 total
includes taxes & fees
30 Mar - 31 Mar
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
The Buckmaster Inn
Exterior

The Buckmaster Inn

3.0 star property
10.0 out of 10, Exceptional, (60)
"I had a great stay at the Buckmaster Inn for ski weekend at Okemo. The house is beautiful with many classic colonial touches throughout. Best of all, Richard and Elizabeth are gracious hosts who go above and beyond to make their guests comfortable. It snowed the last night of my stay and Richard got up extra early to clear the driveway and my car! I will be back whenever I can visit. "
The Buckmaster Inn
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 334
SAR 617 total
includes taxes & fees
16 Apr - 17 Apr
King & Queen Suite in Historic Inn Circa 1780
Golden Stage Inn B&B
Seasonal outdoor pool

Golden Stage Inn B&B

3.5 star property
10.0 out of 10, Exceptional, (26)
"Family run B&B close to Okemo. Wonderful hosts. "
Golden Stage Inn B&B
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)
"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 334
SAR 584 total
includes taxes & fees
16 Apr - 17 Apr
Room in Historic Inn! 20 Minutes to Okemo!
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)
"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 371
SAR 626 total
includes taxes & fees
16 Apr - 17 Apr
Honeymoon Suite with Jacuzzi Tub in Historic 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 Woodstocker B&B
Woodbridge Inn
Front of property - evening/night

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
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
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Terrace/patio

Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature

Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Inn at Water's Edge
Bar (on property)

Inn at Water's Edge

3.0 star property
Inn at Water's Edge
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

Mountain Green
Indoor pool

Mountain Green

2.0 star property
5.8 out of 10, (8)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is SAR 878
SAR 1,177 total
includes taxes & fees
23 Mar - 24 Mar
Mountain Green
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (69)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is SAR 315
SAR 1,026 total
includes taxes & fees
3 Apr - 4 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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. 12 mi (19.3 km) from the heart of downtown.
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.