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Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Tonight
Sep 17 - Sep 18
Tomorrow
Sep 18 - Sep 19
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Pittsfield hotels with a pool

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A garden with wooden Adirondack chairs and a stone pathway.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩108,499
₩151,644 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
A hot tub area with a pool, lounge chairs, and a caution sign.
A bathroom with a large mirror, a sink, and a towel rack.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
₩158,355
₩176,882 total
includes taxes & fees
Oct 15 - Oct 16
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
  • Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
₩199,388
₩222,717 total
includes taxes & fees
Sep 20 - Sep 21
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

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

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.
₩173,109
₩193,364 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.
A bathroom with a bathtub, toilet, and shower.
A motel with a parking lot, a swimming pool, and outdoor seating.

5. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
₩117,210
₩130,924 total
includes taxes & fees
Sep 20 - Sep 21
Berkshire Inn
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩158,115
₩176,614 total
includes taxes & fees
Sep 22 - Sep 23
The Yankee Inn
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
₩178,697
₩199,603 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn & Suites Berkshires-Lenox
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A bathroom with a white sink, mirror, and toilet.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
₩107,682
₩120,281 total
includes taxes & fees
Sep 20 - Sep 21
Howard Johnson by Wyndham Lenox
A spacious living room with a fireplace, comfortable seating, and large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
₩129,686
₩159,814 total
includes taxes & fees
Sep 21 - Sep 22
Vacation Village in the Berkshires
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

10. Courtyard by Marriott Lenox Berkshires

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.
₩222,424
₩248,448 total
includes taxes & fees
Sep 22 - Sep 23
Courtyard by Marriott Lenox Berkshires
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Spacious condo in a beautiful setting with great views, and amenities (pools, fire pits , and hot-tub). Loved it !"
Corinne 1-night trip
Posted 12 hours ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
Dolores 3-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Judith 1-night trip
Posted 2 days ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Nice place, would stay again"
kaitlyn 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Hotel was very clean, spacious, and staff was very courteous. Bar and restaurant onsite are hood, Guidos market is right in front and is AMAZING!! Definitely a great value and comfortable!"
Kristen 2-night trip
Posted 2 days ago
Hilton Garden Inn Lenox Pittsfield

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 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 Pontoosuc Lake and Housatonic River. During your stay, check out sights such as Berkshire Museum, Bousquet Ski Area, and Hancock Shaker Village. 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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