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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 35 B&B in Windsor with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Quiet, friendly, convenient"
The price is AED 498
AED 700 total
includes taxes & fees
29 May - 30 May
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (262)
"Wonderful Location"
Lakehouse Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (472)
"Great historic inn loaded with interesting common areas and furnishings."
The price is AED 663
AED 811 total
includes taxes & fees
10 Jun - 11 Jun
Whistler's Inn Bed & Breakfast
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
The price is AED 988
AED 988 total
includes taxes & fees
29 May - 30 May
Tanglewood Suites
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (412)
"Nice"
The price is AED 542
AED 594 total
includes taxes & fees
3 Jun - 4 Jun
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (364)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 698
AED 779 total
includes taxes & fees
29 May - 30 May
Chambery Inn
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (129)
"Best place I have been. Beautiful place. Excellent host. "
The price is AED 638
AED 713 total
includes taxes & fees
29 May - 30 May
The Trail in Adams - Berkshires’ Art Hotel
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (125)
"Very enjoyable comfortable stay"
The price is AED 1,025
AED 1,145 total
includes taxes & fees
29 May - 30 May
Devonfield Inn B&B
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"The Inn was welcoming and comfortable with homemade cookies waiting for us at check in! The decor was especially inviting, we loved it! The staff that took our breakfast order, was equally warm, inviting, and accommodating. "
The price is AED 621
AED 670 total
includes taxes & fees
10 Jun - 11 Jun
Inn at Silver Maple Farm
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is AED 890
AED 995 total
includes taxes & fees
30 May - 31 May
Brook Farm Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is AED 1,441
AED 1,610 total
includes taxes & fees
29 May - 30 May
33 Main
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is AED 1,263
AED 1,528 total
includes taxes & fees
2 Jun - 3 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
Inn at Kenmore Hall
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is AED 867
AED 917 total
includes taxes & fees
2 Jun - 3 Jun
Harbour House Inn
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Great host and enjoyable stay."
Eastgate Inn B&B
Berkshire Mountain House
Comfort Apartment, 1 Bedroom, Mountain View, Garden Area | Private kitchenette | Mini-fridge, paper towels

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (24)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
The Red Door B&B
Interior

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
The price is AED 547
AED 578 total
includes taxes & fees
26 Jun - 27 Jun
UU Rowe Camp and Conference Center
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

Elegant suite with a king bed, fireplace, and kitchenette.

The price is AED 1,579
AED 2,145 total
includes taxes & fees
4 Jun - 5 Jun
Elegant suite with a king bed, fireplace, and kitchenette.
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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Frequently asked questions

Searching for B&Bs in Windsor?
If you want to find an accommodation with fewer rooms than the traditional hotel and a cozy environment, a B&B may be the perfect thing for your trip to Windsor.
How do you know if a B&B is the right choice for you?
B&Bs all have a unique charm. Whether it’s a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.
What are the top B&Bs in Windsor?
Below are some well-liked B&Bs in the area: The Cornell Inn, Lenox & The Berkshires: 15.6 mi (25.1 km) from the heart of Windsor. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. Situated 16.8 mi (27 km) from the heart of Windsor. Enjoy the free full breakfast and deli. Whistler’s Inn Bed & Breakfast: 14 rooms. 15.8 mi (25.4 km) from the heart of downtown. Enjoy the private yard and unique décor. Chambery Inn: 9 rooms. Located 17.4 mi (28 km) from the core of Windsor. Enjoy the private yard and deli.
When is the best time to book my B&B in Windsor?
When you’re planning your escape to 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 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Windsor?
Spend some time exploring Savoy Mountain State Forest and Mohawk Trail State Forest if you’re hoping to see some of the area’s natural features. You might put Berkshire East Ski Resort and Jiminy Peak Mountain Resort on your list if you want to see more of the area.
How can I get to and around Windsor?
Mapping out your trip in and around Windsor is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you’d like to explore around the area, you may want a rental car for your journey.