Photo by William E Berry Jr.

Search B&B in Windsor

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

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

The Jackson
Exterior

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (209)
"The beds are extremely comfortable. The availability of ice is a nice feature. The flavored coffee machine was a nice surprise. Great recommendations from David. We will be back"
The price is SAR 791
SAR 870 total
includes taxes & fees
21 Apr - 22 Apr
The Jackson
Snowed Inn
Front of property

Snowed Inn

3.5 star property
9.8 out of 10, Exceptional, (344)
"Such a beautiful and cozy place to stay!! Welcoming atmosphere and people! Had a wonderful time!"
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 408
SAR 449 total
includes taxes & fees
21 Apr - 22 Apr
The Vesper
Mountain Valley Retreat
Exterior

Mountain Valley Retreat

2.5 star property
9.6 out of 10, Exceptional, (171)
"Place is away from hotels and restaurant strip. Very relaxing place, excellent breakfast. Will go back."
The price is SAR 413
SAR 466 total
includes taxes & fees
22 Apr - 23 Apr
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 747
SAR 821 total
includes taxes & fees
20 Apr - 21 Apr
Stay At Jimmy's
Harvest Barn Inn
Exterior

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (209)
"Great accomodations. Kaelan & Blessing were wonderful hosts and very accommodating to my requests. The breakfasts were excellent - well-balanced, nutritious, and filling. A quaint, inn in a quiet location with a nice view. A very nice weekend stay at a very reasonable price. Would highly recommend, and would certainly stay there again."
The price is SAR 591
SAR 644 total
includes taxes & fees
27 Apr - 28 Apr
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 1,244
SAR 1,356 total
includes taxes & fees
21 Apr - 22 Apr
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."
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)
"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
20 Apr - 21 Apr
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)
"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
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 616
SAR 668 total
includes taxes & fees
1 May - 2 May
Dexter's Inn
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
1 bedroom, iron/ironing board, WiFi, bed sheets

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
20 Apr - 21 Apr
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Terrace/patio

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 618 total
includes taxes & fees
21 Apr - 22 Apr
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)
"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
20 Apr - 21 Apr
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)
"Family run B&B close to Okemo. Wonderful hosts. "
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)
"Darling -- Wonderful location, hosts and great breakfast -- We will be back during ski season. Thank you. "
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 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
20 Apr - 21 Apr
Whimsical Vermont Farmhouse – Cozy, Inspiring & Close to Nature
Windsor Mansion Inn
Exterior

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)
"Clean and comfortable with a beautiful sunrise view."
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
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)
"This was our second stay at the cozy cottage amd was just as enjoyable as the first time . Glenn and Melanie are very responsive and like to makesure their guests are comfortable and happy . We loved waking up on the lake and enjoyed the back deck and firepit. We look forward to renting here again in the future. P"
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, (156)
"Two friends and I stayed at this house for the second year in a row. It has been a perfect place for us, being 10 minutes away from Grafton and 25 minutes from Okemo."
The price is SAR 638
SAR 1,362 total
includes taxes & fees
21 Apr - 22 Apr
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. 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.