Find Hotels with a Pool in Pittsfield, MA
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Our top choices for Pittsfield hotels with a pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
Jeffrey
$97 nightly
The price is $108
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
8.0 out of 10, Very Good, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Berkshire Mountain Lodge
Pittsfield
9.0 out of 10, Wonderful, (784)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
Michelle
$108 nightly
The price is $120
Jan 8 - Jan 9, 2026
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
Kristen
$103 nightly
The price is $115
Dec 21 - Dec 22
Total with taxes and fees
Berkshire Inn
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
MARIA J
$82 nightly
The price is $92
Dec 16 - Dec 17
Total with taxes and fees
Element Lenox Berkshires
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
joel
$131 nightly
The price is $146
Dec 16 - Dec 17
Total with taxes and fees
Prospect Berkshires
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
"
Laura
$250 nightly
The price is $280
Dec 10 - Dec 11
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
8.8 out of 10, Excellent, (706)
"Great hospitality "
regina maria
$102 nightly
The price is $114
Dec 15 - Dec 16
Total with taxes and fees
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.
Top Pittsfield Hotel Reviews
Comfort Inn & Suites East Greenbush - Albany
10/10 Excellent
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