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Aug 15 - Aug 17
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Aug 22 - Aug 24
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B&B in Chesterfield

The Ellery
Relax in a spacious room with a large window, central seating area, and dining table.

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (782)
"Wonderful breakfast and cute and cozy lobby "
$140 nightly
The price is $156
Aug 17 - Aug 18
Total includes taxes and fees
The Ellery
Black Walnut Inn
Cozy retreat with a large bed, nightstands, and artwork adorns the walls.

Black Walnut Inn

2.0 star property
9.8 out of 10, Exceptional, (77)
"Was a wonderful inn and breakfast absolutely delicious!"
$233 nightly
The price is $260
Aug 10 - Aug 11
Total includes taxes and fees
Black Walnut Inn
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 "
$183 nightly
The price is $205
Aug 14 - Aug 15
Total includes taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Old Mill Inn
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, white cabinetry, and a tiled backsplash.

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (488)
"The staff were very polite and accomodatin"
$235 nightly
The price is $262
Aug 10 - Aug 11
Total includes taxes and fees
Old Mill Inn
Daniel Stebbins House
A charming two-story home with a green door and picket fence, surrounded by a beautifully manicured lawn and flowering bushes.

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (46)
"Beautiful home that provided a relaxed, comfortable stay. If we are in the area again we would definitely return."
$270 nightly
The price is $302
Aug 10 - Aug 11
Total includes taxes and fees
Daniel Stebbins House
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!! "
$237 nightly
The price is $251
Aug 18 - Aug 19
Total includes taxes and fees
Harbour House Inn
The Red Door B&B
Welcome to The Red Door B&B, a charming two-story home surrounded by a lush lawn and trees, with a cozy porch and a white picket fence.

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 Chesterfield 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 18 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG