The Best Pittsfield Hotels with Pools from $98 - 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. FairBridge Inn Express : Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG : Features 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. Hotel On North : 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

Berkshire Mountain Lodge

Pittsfield

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

$155 nightly

Aug 19 - Aug 20

Total with taxes and fees

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

The Yankee Inn

Lenox

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

$169 nightly

Jul 22 - Jul 23

Total with taxes and fees

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

$130 nightly

Jul 23 - Jul 24

Total with taxes and fees

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.

$145 nightly

Jul 26 - Jul 27

Total with taxes and fees

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

Hampton Inn & Suites Berkshires-Lenox

Lenox

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

$188 nightly

Aug 19 - Aug 20

Total with taxes and fees

Element by Marriott Lenox Berkshires

Lenox

Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.

$229 nightly

Jul 27 - Jul 28

Total with taxes and fees

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

$196 nightly

Jul 22 - Jul 23

Total with taxes and fees

Howard Johnson by Wyndham Lenox

Lenox

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

$98 nightly

Jul 30 - Jul 31

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

Berkshire Inn

8/10 Good

"Totally adequate for 3 days. Comfortable bed."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very comfortable. The coffee was good. But,my one note would be there wasn't anything else offered for breakfast that my picky eater teenager would eat."

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. FairBridge Inn Express: Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Features 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. Hotel On North: 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 Housatonic River and Onota Lake. During your stay, check out sights such as Berkshire Museum, Colonial Theater, and Bousquet Ski Area. 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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