Find Hotels with a Pool in Pittsfield, MA
Check availability on Pittsfield Hotels with a Pool
Our top choices for Pittsfield hotels with a pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (997)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
$98 nightly
The price is $109
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHGPittsfield
9.2 out of 10, Wonderful, (68)
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
Jeanne
$113 nightly
The price is $126
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
Christine
$128 nightly
The price is $143
Jan 2 - Jan 3, 2026
Total with taxes and fees
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
$79 nightly
The price is $89
Dec 24 - Dec 25
Total with taxes and fees
9.0 out of 10, Wonderful, (794)
"Spacious room and loved pool and hot tub!"
Deanna
$108 nightly
The price is $120
Jan 21 - Jan 22, 2026
Total with taxes and fees
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
Morgan
$135 nightly
The price is $151
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$196 nightly
The price is $219
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8.8 out of 10, Excellent, (710)
"Great hospitality "
regina maria
$107 nightly
The price is $120
Jan 4 - Jan 5, 2026
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
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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