🏊 Top 10 Pittsfield Hotels with Swimming Pool

Q: What are some accommodation options with pools in Pittsfield?

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

RM756 total

includes taxes & fees

12 Jul - 13 Jul

Berkshire Inn

Pittsfield

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

RM409 total

includes taxes & fees

14 Jul - 15 Jul

Berkshire Mountain Lodge

Pittsfield

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

RM701 total

includes taxes & fees

6 Aug - 7 Aug

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

RM1,003 total

includes taxes & fees

12 Jul - 13 Jul

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

RM691 total

includes taxes & fees

4 Aug - 5 Aug

Indoor pool, open 6:00 AM to 10 PM, pool loungers

Hotel Downstreet, an Ascend Collection Hotel

North Adams

Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.

RM785 total

includes taxes & fees

12 Jul - 13 Jul

The Porches Inn at Mass MoCA

North Adams

Float peacefully day or night at this 24-hour outdoor pool and hot tub sanctuary.

RM1,151 total

includes taxes & fees

28 Jul - 29 Jul

Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.

RM500 total

includes taxes & fees

22 Jul - 23 Jul

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Recommend for amenities"

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"This was a nice hotel. The rooms are nice and spacious. They are a little dated but clean. The breakfast was a nice full breakfast. The pool was a little cold but clean. There was some wear and tear where wall paper was peeling off the wall and they were muddying over the top but it was sloppily done and some cracks in the walls in the bathroom. But other than that it was a nice place. Our room on the 3rd floor was quiet but when I walked down the hallway on the 2nd floor to breakfast, 2 rooms had dogs that would bark like crazy when you walked by. That would have been annoying if I was next to them being woken up early in the morning. So make sure you’re in a room not next to animals. Overall it was a good experience. It was safe and convenient to the freeway and a gas station."

The Red Lion Inn

10/10 Excellent

"Staff was very helpful particularly Jerry in outside cafe. Grounds keeper did a beautiful job! Outdoor pool was amazing! Will be back to swim in in the winter. Loved the shops located in the main building. We stayed in Maple Glen which was lovely. I was disappointed my room was dark but now know to ask for a sunnier room when booking."

Hilton Garden Inn Lenox Pittsfield

10/10 Excellent

"Beds were extremely comfortable. Thai fusion restaurant, Jae’s, in lobby, was delicious. Bartenders were efficient and friendly. Location is 5 minute drive to downtown Lenox and Tanglewood and a 1 minute walk to Guidos, the best small specialty market (gifts, garden, fresh seafood, butcher, deli, liquors) we have ever experienced."

Frequently asked questions

What are some accommodation options with pools in Pittsfield?

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

What is there to see and do in Pittsfield?

Surround yourself with nature at Housatonic River and Canoe Meadows Wildlife Sanctuary. During your stay, visit sights such as Berkshire Museum, Colonial Theater and Barrington Stage Company. The sporting events and theatre 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 the local weather in Pittsfield into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 very many public transport options, so consider a car rental to maximise your time.

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Check availability on Pittsfield Hotels with Swimming Pools

Our top choices for Pittsfield hotels with a pool

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

Berkshire Inn

Berkshire Mountain Lodge

Hilton Garden Inn Lenox Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hotel Downstreet, an Ascend Collection Hotel

The Porches Inn at Mass MoCA

Sunset Inn

Devonfield Inn B&B

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Choose what matters most at hotels with a pool in Pittsfield

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Comfort Inn & Suites East Greenbush - Albany

Hotel Downstreet, an Ascend Collection Hotel

The Yankee Inn

Berkshire Inn

The Red Lion Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

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