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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

B&B in Windsor

The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
$163 nightly
The price is $182
Sep 1 - Sep 2
Total includes taxes and fees
The Cornell Inn, Lenox & The Berkshires
Whistler's Inn Bed & Breakfast
Stroll through the beautifully manicured lawn and discover a vibrant garden filled with lush purple flowering bushes.

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (479)
"Nice quaint out of the ordinary vacation experience. "
$182 nightly
The price is $203
Aug 10 - Aug 11
Total includes taxes and fees
Whistler's Inn Bed & Breakfast
The Trail in Adams - Berkshires’ Art Hotel
Cozy cabin with a spacious living area, featuring a glass-top table and comfortable seating, and a separate kitchen area with a refrigerator and microwave.

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (132)
"Stayed only one night Very cosy, quiet place "
$190 nightly
The price is $212
Aug 12 - Aug 13
Total includes taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Shaker Mill Inn
Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (419)
"Nice stay"
$177 nightly
The price is $195
Aug 12 - Aug 13
Total includes taxes and fees
Shaker Mill Inn
Lakehouse Inn
Relax on the deck with a glass of wine, taking in the serene views of the surrounding water and lush landscape.

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (276)
"Great Views & Hospitality"
Lakehouse Inn
Inn at Silver Maple Farm
Set amidst lush greenery, this multi-story property features distinct buildings with gabled and flat roofs.

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (91)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
$209 nightly
The price is $234
Sep 2 - Sep 3
Total includes taxes and fees
Inn at Silver Maple Farm
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (155)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
$254 nightly
The price is $284
Sep 3 - Sep 4
Total includes taxes and fees
Brook Farm Inn
Tanglewood Suites
Relax in this serene bedroom with a large bed, two chairs, and a small table, surrounded by lush views.

Tanglewood Suites

2.5 star property
7.8 out of 10, Good, (16)
"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. "
$269 nightly
The price is $269
Aug 10 - Aug 11
Total includes taxes and fees
Tanglewood Suites
33 Main
Features a sleek glass-enclosed shower, vanity with sink and mirror, toilet, and bidet.

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
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"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. "
$250 nightly
The price is $279
Aug 11 - Aug 12
Total includes taxes and fees
Chambery Inn
Harbour House Inn
Stunning traditional architecture with a central entrance and beautifully landscaped surroundings.

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
$239 nightly
The price is $253
Aug 26 - Aug 27
Total includes taxes and fees
Harbour House Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

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 "
$374 nightly
The price is $418
Aug 26 - Aug 27
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Inn at Stockbridge
Stroll through the serene park and enjoy the soothing sounds of the multi-tiered fountain surrounded by lush trees and a shaded walkway.

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Berkshire Mountain House
Enjoy meals in the kitchen with a dining table and chairs, microwave, toaster, and stove.

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (26)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
$309 nightly
The price is $345
Sep 2 - Sep 3
Total includes taxes and fees
Devonfield Inn B&B
Inn at Kenmore Hall
Guests can enjoy a peaceful atmosphere in this elegant space, featuring a console table with decorative items, a potted plant, and a framed photograph.

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
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Cozy retreat with a dresser, comfortable bed, and a warm throw blanket.

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

$232 nightly
The price is $299
Sep 1 - Sep 2
Total includes taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Eastgate Inn B&B
Relax in a cozy outdoor space with wicker chairs and a small table.

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (69)
"Dahlia is great. Excellent accommodation. We walked to Tanglewood "
Eastgate Inn B&B
The Red Door B&B
Enjoy a serene view of the lush garden from the comfort of your room.

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
The Red Door B&B
UU Rowe Camp and Conference Center
Stroll up to this charming two-story home, featuring a welcoming front porch and a staircase leading to the upper floor.

UU Rowe Camp and Conference Center

2.0 star property
UU Rowe Camp and Conference Center
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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Top Windsor Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."
Susan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What is the nightly rate for a B&B in Windsor?
Prices for B&Bs in Windsor often vary, but you can find a great deal from $182 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
What is the difference between a Windsor B&B and a hotel?
Every Windsor B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windsor B&Bs.