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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

B&B in Windsor

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Quiet, friendly, convenient"
The price is SAR 483
SAR 686 total
includes taxes & fees
22 Jun - 23 Jun
The Cornell Inn, Lenox & The Berkshires
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

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 SAR 1,009
SAR 1,009 total
includes taxes & fees
29 Jun - 30 Jun
Tanglewood Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (264)
"Really peaceful and serene property due to the lake. The house was clean and the staff were friendly. "
Lakehouse Inn
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (86)
"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 SAR 709
SAR 766 total
includes taxes & fees
23 Jun - 24 Jun
Inn at Silver Maple Farm
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)
"Stayed only one night Very cosy, quiet place "
The price is SAR 652
SAR 728 total
includes taxes & fees
22 Jun - 23 Jun
The Trail in Adams - Berkshires’ Art Hotel
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (412)
"Nice"
The price is SAR 529
SAR 580 total
includes taxes & fees
23 Jun - 24 Jun
Shaker Mill 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 SAR 611
SAR 754 total
includes taxes & fees
22 Jun - 23 Jun
Whistler's Inn Bed & Breakfast
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (365)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (126)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
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 SAR 1,290
SAR 1,561 total
includes taxes & fees
23 Jun - 24 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
33 Main
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
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall
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 SAR 886
SAR 936 total
includes taxes & fees
23 Jun - 24 Jun
Harbour House Inn
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The price is SAR 747
SAR 1,094 total
includes taxes & fees
22 Jun - 23 Jun
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

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

The price is SAR 1,497
SAR 2,024 total
includes taxes & fees
22 Jun - 23 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. Located 15.8 mi (25.4 km) from the core of Windsor. Enjoy the private yard and unique décor.
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.