The Best Hotels with a Pool in Pittsfield, MA from AED 369 in 2026

Q: What are some accommodations with pools in Pittsfield?

Berkshire Mountain Lodge : Features free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express : Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG : Features a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North : Features a snack bar/deli, a pool, and complimentary wired internet access.

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Our top choices for Pittsfield hotels with a pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

AED 594 total

includes taxes & fees

26 Jul - 27 Jul

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

AED 834 total

includes taxes & fees

26 Jul - 27 Jul

Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

AED 630 total

includes taxes & fees

19 Aug - 20 Aug

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.

AED 532 total

includes taxes & fees

26 Jul - 27 Jul

Berkshire Inn

Pittsfield

Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.

AED 369 total

includes taxes & fees

22 Jul - 23 Jul

Devonfield Inn B&B

Lee

Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.

AED 1,801 total

includes taxes & fees

22 Jul - 23 Jul

The Inn at Stockbridge

Stockbridge

Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.

AED 1,597 total

includes taxes & fees

27 Jul - 28 Jul

Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

Prospect Berkshires

Egremont

Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.

AED 1,655 total

includes taxes & fees

28 Jul - 29 Jul

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"As of late we have been traveling with our small dog. Most hotels that accept pets you end up in the most dinghy room and not kept well. Not here the room was clean well kept and no odor. "

The Yankee Inn

10/10 Excellent

"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."

The Red Lion Inn

8/10 Good

"Dinner in the main dining room was amazing! Food delicious and staff attentive. We stayed in the Stephen’s House and arrived in the dark. It was not well lighted and 184 was up a huge flight of stairs. We had to haul up too many bags! We would have done a sm. 1 night bag If we had known this was a second floor. Beds were very uncomfortable soft and towels with stains. The kitchen area was without a refrigerator turned on and no ice. The front desk attendant was very efficient and ran some ice over! We love Red Lion Inn and found some things a bit off this time."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very comfortable. The coffee was good. But,my one note would be there wasn't anything else offered for breakfast that my picky eater teenager would eat."

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Frequently asked questions

What are some accommodations with pools in Pittsfield?

Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Features a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North: Features a snack bar/deli, a pool, and complimentary wired internet access.

What is there to see and do in Pittsfield?

Surround yourself with nature at Housatonic River and Onota Lake. During your stay, check out sights such as Berkshire Museum, Colonial Theater, 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.

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Our top choices for Pittsfield hotels with a pool