TOP Hotels with Swimming 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. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG : Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. FairBridge Inn Express : Offers 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. Holiday Inn & Suites Pittsfield-Berkshires by IHG : 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

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

₹12,673 total

includes taxes & fees

3 Sept - 4 Sept

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

2. The Yankee Inn

Lenox

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

₹18,645 total

includes taxes & fees

10 Aug - 11 Aug

3. Berkshire Inn

Pittsfield

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

₹9,583 total

includes taxes & fees

12 Aug - 13 Aug

4. Berkshire Mountain Lodge

Pittsfield

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

₹15,472 total

includes taxes & fees

30 Aug - 31 Aug

5. Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

₹20,486 total

includes taxes & fees

23 Aug - 24 Aug

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

6. Hampton Inn & Suites Berkshires-Lenox

Lenox

Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.

₹16,527 total

includes taxes & fees

23 Aug - 24 Aug

7. 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.

₹16,194 total

includes taxes & fees

1 Sept - 2 Sept

8. Courtyard by Marriott Lenox Berkshires

Lenox

Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness centre.

₹22,550 total

includes taxes & fees

19 Aug - 20 Aug

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"

Quality Inn Great Barrington

10/10 Excellent

"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"Conveniently located near the highway and a gas station. Breakfast included daily. Coffee is from an automatic dispenser, so not great, but it is plentiful. Good water pressure and soft towels. Beds were clean and comfortable. Had an issue with the ac/heat in my room and was switched to a new room without too much trouble, even though it was the middle of the night. Grateful for their help with making that happen so quickly."

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. FairBridge Inn Express: Offers 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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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 Pontoosuc Lake and Housatonic River. 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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Our top choices for Pittsfield hotels with a pool