The Best Hotels with a Pool in Pittsfield, MA from AED 324 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 : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North : Provides a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites : 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

A building entrance with a large planter with purple flowers and a small tree.

1. Hotel On North

Pittsfield

Philip

AED 471 total

includes taxes & fees

1 Dec - 2 Dec

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

2. The Central Downtown Inn & Suites

Pittsfield

Debra

AED 406 total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

3. Berkshire Inn

Pittsfield

cheryl

AED 335 total

includes taxes & fees

1 Dec - 2 Dec

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Pittsfield

Yuguo

AED 423 total

includes taxes & fees

30 Nov - 1 Dec

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

5. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

AED 487 total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

6. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

AED 384 total

includes taxes & fees

1 Dec - 2 Dec

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

7. Berkshire Mountain Lodge

Pittsfield

Charline

AED 421 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

Pittsfield

William

AED 277 total

includes taxes & fees

15 Nov - 16 Nov

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"breakfast needs more variety, great staff but understaffed, great location, ty to change the linens at least every other day"

The Yankee Inn

10/10 Excellent

"The Yankee Inn was clean and on a beautiful property. The beds were extremely comfortable. We enjoyed the morning breakfast, and the staff was extremely kind and helpful. If you book through Expedia - I would call ahead to verify the specifics of the room you have reserved, as Expedia’s description of the room I reserved didn’t match the description on the actual Yankee Inn website. Through Expedia, I reserved a King Deluxe with fireplace, balcony and mountain view. But the actual Yankee Inn website offers EITHER a King Deluxe with a fireplace and balcony OR King Deluxe with mountain view. The management made amends to accommodate as much as possible, but the Expedia advertising was a bit misleading in my opinion."

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: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North: Provides a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: 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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