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. FairBridge Inn Express : Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North : Provides a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites : 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

1. Vacation Village in the Berkshires

Williamstown

Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.

$108 nightly

Nov 16 - Nov 17

Total with taxes and fees

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

2. Berkshire Mountain Lodge

Pittsfield

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

$107 nightly

Dec 15 - Dec 16

Total with taxes and fees

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

3. The Yankee Inn

Lenox

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

$126 nightly

Dec 12 - Dec 13

Total with taxes and fees

An indoor swimming pool with clear water, tiled floors, and a blue wall.

4. 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.

$103 nightly

Dec 13 - Dec 14

Total with taxes and fees

A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

5. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

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

$105 nightly

Dec 11 - Dec 12

Total with taxes and fees

An indoor swimming pool with lounge chairs, a diving board, and a window with a view of trees.

6. Hampton Inn & Suites Berkshires-Lenox

Lenox

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

$108 nightly

Dec 15 - Dec 16

Total with taxes and fees

A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.

7. Element by Marriott Lenox Berkshires

Lenox

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

$135 nightly

Nov 29 - Nov 30

Total with taxes and fees

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

8. Hilton Garden Inn Lenox Pittsfield

Pittsfield

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

$119 nightly

Nov 22 - Nov 23

Total with taxes and fees

An indoor swimming pool with clear blue water, surrounded by windows with a view of trees.

9. Courtyard by Marriott Lenox Berkshires

Lenox

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

$114 nightly

Dec 13 - Dec 14

Total with taxes and fees

A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.

10. Howard Johnson by Wyndham Lenox

Lenox

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

$79 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included

Hot tub

Find out more about Pittsfield

Discover top Pittsfield attractions

Pittsfield, a hidden gem in the Berkshires, offers a delightful mix of cultural attractions and outdoor adventures perfect for travelers seeking quality experiences. Begin your exploration at the vibrant downtown area, where charming boutiques and artisanal shops invite leisurely strolls. Just a short drive away, you can immerse yourself in the rich history of the area with a visit to a historic estate, where guided tours reveal fascinating stories of the past. For art enthusiasts, the local galleries showcase impressive works from both emerging and established artists, providing a perfect opportunity to discover unique pieces. If you're looking for outdoor fun, the nearby scenic trails promise breathtaking views and refreshing hikes suitable for families. After a day of adventure, unwind at one of the area’s upscale accommodations, known for their attentive service and luxurious amenities, ensuring that your stay is as memorable as your experiences. With so much to see and do, Pittsfield promises an enjoyable and well-rounded getaway.

Top Pittsfield Hotel Reviews

The Yankee Inn

8/10 Good

"Everything about this place was wonderful! The location, the staff, the cleanliness. The only downsize was we booked this property because of the pool and it was under maintenance during my stay. A notice would have been nice :( Other than that, beautiful inn."

Vacation Village in the Berkshires

8/10 Good

"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."

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: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North: Provides a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: 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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