TOP Hotels with Pool in Pittsfield, MA for 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Pool

Tonight

Tomorrow

Next weekend

In two weeks

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.

Rp2.972.440 total

includes taxes & fees

22 Jun - 23 Jun

Berkshire Mountain Lodge

Pittsfield

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

Rp2.825.564 total

includes taxes & fees

18 Jun - 19 Jun

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

Rp3.169.257 total

includes taxes & fees

22 Jun - 23 Jun

Berkshire Inn

Pittsfield

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

Rp1.715.466 total

includes taxes & fees

16 Jun - 17 Jun

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

Rp2.413.958 total

includes taxes & fees

22 Jun - 23 Jun

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

Rp2.090.692 total

includes taxes & fees

15 Jun - 16 Jun

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

Rp1.755.566 total

includes taxes & fees

15 Jun - 16 Jun

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

Rp1.314.139 total

includes taxes & fees

14 Jun - 15 Jun

View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Very clean. Accessible room was spacious. However, very little turning radius in bathroom, toilet not elevated and can’t fit under vanity."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"From my check-in, throughout my stay and my check-out, everything was great! The staff were helpful and friendly. It was nice to have hot water for my showers. The breakfast was fantastic! Dinner was excellent. I look forward to my visit next week."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"The view was great. It is in 10 to 30 minutes of places I wanted to visit. The staff went out of their way to accommodate me with the personal items I needed. I didn't need to use the Kayaks or pontoon that they rent to use on Lake Laural. The only drawback is no beach."

The Red Lion Inn

8/10 Good

"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We did enjoy getting a cocktail from the bar and sitting in rockers on the front porch, watching the traffic go by."

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

Explore a world of travel with Expedia

More ways to book

Book Hotels with Pool in Pittsfield on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Pittsfield Hotels with Pool

Our top choices for Pittsfield hotels with a pool