Hotels with Swimming Pool in Pittsfield, Massachusetts

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Check availability on Pittsfield Hotels with Swimming Pool

Tonight
Jul 5 - Jul 6
Tomorrow
Jul 6 - Jul 7
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Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20

Top Pittsfield Hotels with Swimming Pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (809)
"Staff was welcoming and informative "
The price is P6,940
P7,752 total
includes taxes & fees
Jul 13 - Jul 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (502)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
The price is P8,559
P9,561 total
includes taxes & fees
Jul 7 - Jul 8
Holiday Inn Express & Suites Pittsfield - Berkshires
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (777)
"The motel was nicely done and clean. The beds were comfortable "
The price is P5,400
P6,032 total
includes taxes & fees
Jul 6 - Jul 7
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P12,638
P14,117 total
includes taxes & fees
Jul 15 - Jul 16
Hilton Garden Inn Lenox Pittsfield
Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1003)
"Fantastic place"
The price is P8,106
P9,054 total
includes taxes & fees
Aug 3 - Aug 4
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Exterior

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (394)
"Perfect for our needs"
The price is P11,943
P14,600 total
includes taxes & fees
Aug 4 - Aug 5
The Porches Inn at Mass MoCA
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (386)
"No frills but it was a great stay!"
The price is P4,810
P5,373 total
includes taxes & fees
Jul 9 - Jul 10
Sunset Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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.

Frequently asked questions

What's it like visiting Pittsfield?
If relaxing by the pool is your idea of the perfect getaway, you may want to consider historic Pittsfield, which offers 7 places to stay with pools. During your trip, you can explore sights such as Jiminy Peak Mountain Resort and Norman Rockwell Museum, and then relax and unwind poolside at one of the accommodations in Pittsfield that guests like for their pools.
What are some accommodations with pools in Pittsfield?
Best Western Plus Berkshire Hills Inn & Suites: Offers a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers a snack bar/deli, a pool, and complimentary wired internet access. Hotel On North: Features free self parking, an indoor pool, and complimentary wireless internet access.
How many pool hotels can I expect to find in Pittsfield?
Expedia has 7 hotels in Pittsfield for your poolside break.
What is there to see and do in Pittsfield?
Make a point to visit attractions like Housatonic River and Berkshire Museum. During your stay, check out sights such as Colonial Theater, Barrington Stage Company, and Bousquet Ski Area. The sporting events and theater scene are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Pittsfield?
Taking into account the local weather in Pittsfield can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to travel around Pittsfield?
Knowing the transportation options in Pittsfield can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options to choose from so consider a car rental to maximize your time.