Top 10 Hotels with Pool & Accommodation in Pittsfield from AU$104

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 - 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 : Offers 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

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

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a spa pool to soothe tired muscles.

includes taxes & fees

14 June - 15 June

Berkshire Mountain Lodge

Pittsfield

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

includes taxes & fees

22 June - 23 June

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

9 June - 10 June

Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

includes taxes & fees

14 June - 15 June

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

22 June - 23 June

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

22 June - 23 June

The Little Lion

Great Barrington

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

includes taxes & fees

10 June - 11 June

Cozy Corner Motel

Williamstown

Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.

includes taxes & fees

17 June - 18 June

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Spa pool

Top Pittsfield Hotel Reviews

The Yankee Inn

10/10 Excellent

"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub for the many surrounding activities--it's slightly over an hour drive to Hartford, and I was happy to leave the hustle and bustle of the city and return to the beauty of the Berkshires. I was surrounded by nature, but a grocery store, pharmacy, laundromat, and stores were also a short distance down the road. An extensive daily breakfast selection surpassed any I've recently had, and I've done my fair share of traveling."

Holiday Inn & Suites Pittsfield-Berkshires by IHG

2/10 Terrible

"The hotel is under construction. This was not mentioned when reservations made. The only available parking was down the street at the bank. The television channels did not come in had to call for assistance. Then tv continued to have issues. On the ceiling and the wall there was dark colored “something” mold? dust? GROSS! Not worth the price."

The Red Lion Inn

10/10 Excellent

"Ideal location if one is looking to stay in Stockbridge. The guest house we stayed in was quiet and comfortable. But our room was looking a little worn and in need of some updates, such as the carpet. The property has an excellent restaurant. The property was undergoing a renovation during our stay, so the parking situation was at first confusing, but we got the hang of it 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. Hotel On North: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Express & Suites Pittsfield - 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: Offers 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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Our top choices for Pittsfield hotels with a pool