Pittsfield Hotels with Pool, Massachusetts: Pittsfield Hotel Guide

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 : Provides 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

Berkshire Inn

Pittsfield

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

includes taxes & fees

6 Jul - 7 Jul

Berkshire Mountain Lodge

Pittsfield

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

includes taxes & fees

9 Jul - 10 Jul

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.

includes taxes & fees

6 Jul - 7 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.

includes taxes & fees

29 Jun - 30 Jun

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

includes taxes & fees

29 Jun - 30 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.

includes taxes & fees

7 Jul - 8 Jul

The Little Lion

Great Barrington

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

includes taxes & fees

25 Jun - 26 Jun

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

includes taxes & fees

1 Jul - 2 Jul

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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

10/10 Excellent

"The room was very clean and comfortable. We stayed on the first floor, which was especially helpful since my husband is a senior. The staff was professional, kind, and welcoming throughout our stay. Breakfast was included and offered several options that worked for us as vegans. I always bring my own plant-based milk, which allows me to enjoy even more of the breakfast offerings. We especially loved the fresh fruit. The location is excellent, with a gas station conveniently located next door, pleasant areas for walking nearby, and a dog-friendly atmosphere. We were so pleased with our experience that we plan to bring our dog with us next time. We highly recommend this hotel and would gladly stay here again."

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."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Property is adequate, though rundown. The building is undergoing renovations, and hopefully, a better hotel will emerge. The suite was clean with nice views of the surrounding area, but the living room area was dated, and the kitchen was undersized. We did not utilize the pool or the restaurant. Overall, I would rank the hotel as good, but be aware that construction is ongoing. Location is very good, within walking distance to several restaurants and stores."

Quality Inn Great Barrington

8/10 Good

"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain time for a gathering."

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: Provides a snack bar/deli, a pool and complimentary high-speed (wired) Internet access.

What is there to see and do in Pittsfield?

Make a point to visit attractions such as Housatonic River and Berkshire Museum. During your stay, visit sights such as Berkshire Athenaeum, 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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