The Best Pittsfield Hotels with Pools from $88 - Hotels with indoor pools in Pittsfield, MA

Q: What are some accommodations 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 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 wired internet access.

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Our top choices for Pittsfield hotels with a pool

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

1. The Yankee Inn

Lenox

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

$175 nightly

Aug 10 - Aug 11

Total with taxes and fees

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

$119 nightly

Sep 3 - Sep 4

Total with taxes and fees

3. Berkshire Mountain Lodge

Pittsfield

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

$138 nightly

Aug 30 - Aug 31

Total with taxes and fees

4. Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

$79 nightly

Aug 30 - Aug 31

Total with taxes and fees

5. Berkshire Inn

Pittsfield

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

$88 nightly

Sep 2 - Sep 3

Total with taxes and fees

6. 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.

$144 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

7. Hampton Inn & Suites Berkshires-Lenox

Lenox

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

$139 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

$192 nightly

Aug 23 - Aug 24

Total with taxes and fees

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

The Yankee Inn

10/10 Excellent

"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. The breakfast is as good as any other hotel brand that offers breakfast. The shopping center is right next door within walking distance, with a few places to eat. It’s a great location also to get to anywhere in the area."

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."

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. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Offers buffet, an indoor pool, and complimentary 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 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, check out sights such as Berkshire Museum, Colonial Theater, and Barrington Stage Company. 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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