🏊 Top 10 Pittsfield Hotels with Swimming Pool

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. FairBridge Inn Express : 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. 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 high-speed (wired) Internet access.

Check availability on Pittsfield Hotels with Swimming Pools

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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, pool loungers

The Yankee Inn

Lenox

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

RM773 total

includes taxes & fees

22 Jul - 23 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.

RM593 total

includes taxes & fees

28 Jul - 29 Jul

Berkshire Mountain Lodge

Pittsfield

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

RM702 total

includes taxes & fees

20 Aug - 21 Aug

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.

RM778 total

includes taxes & fees

26 Jul - 27 Jul

Howard Johnson by Wyndham Lenox

Lenox

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

RM453 total

includes taxes & fees

22 Jul - 23 Jul

Berkshire Inn

Pittsfield

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

RM411 total

includes taxes & fees

22 Jul - 23 Jul

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

Hampton Inn & Suites Berkshires-Lenox

Lenox

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

RM896 total

includes taxes & fees

26 Jul - 27 Jul

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

RM929 total

includes taxes & fees

26 Jul - 27 Jul

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Top Pittsfield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"As of late we have been traveling with our small dog. Most hotels that accept pets you end up in the most dinghy room and not kept well. Not here the room was clean well kept and no odor. "

The Yankee Inn

10/10 Excellent

"The room was neat and had access to outside to enjoy sitting. The fridge in the room was a convenient size for cold and frozen foods. The staff was responsive to issues, even when I told them they could wait to fix it until after we left (it was fixed quickly. The breakfast was excellent and offered a nice variety. Would happily stay here again."

The Red Lion Inn

8/10 Good

"Dinner in the main dining room was amazing! Food delicious and staff attentive. We stayed in the Stephen’s House and arrived in the dark. It was not well lighted and 184 was up a huge flight of stairs. We had to haul up too many bags! We would have done a sm. 1 night bag If we had known this was a second floor. Beds were very uncomfortable soft and towels with stains. The kitchen area was without a refrigerator turned on and no ice. The front desk attendant was very efficient and ran some ice over! We love Red Lion Inn and found some things a bit off this time."

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 accommodation options 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 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. 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 high-speed (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, visit sights such as Berkshire Museum, Colonial Theater and Bousquet Ski Area. 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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Check availability on Pittsfield Hotels with Swimming Pools

Our top choices for Pittsfield hotels with a pool

The Yankee Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Howard Johnson by Wyndham Lenox

Berkshire Inn

Hampton Inn & Suites Berkshires-Lenox

Hilton Garden Inn Lenox Pittsfield

Vacation Village in the Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Choose what matters most at hotels with a pool in Pittsfield

Top Pittsfield Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Vacation Village in the Berkshires

Berkshire Inn

Comfort Inn & Suites East Greenbush - Albany

The Yankee Inn

The Red Lion Inn

Hotel Downstreet, an Ascend Collection Hotel

Holiday Inn & Suites Pittsfield-Berkshires by IHG

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