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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
Aug 22 - Aug 23
Tomorrow
Aug 23 - Aug 24
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for Pittsfield hotels with a pool

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A spacious lobby with a fireplace, seating area, and a bar.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$125 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
An indoor swimming pool with clear water, surrounded by white lounge chairs and a tiled deck.
A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.
A Holiday Inn & Suites hotel with a modern design, featuring a prominent sign and a well-lit entrance.

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.
$119 nightly
$133 total
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A hotel patio with outdoor seating and a fire pit.
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
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.
$146 nightly
$163 total
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.
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.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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.
$127 nightly
$142 total
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A motel with a parking lot, a swimming pool, and outdoor seating.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A bathroom with a bathtub, toilet, and shower.

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.
$88 nightly
$98 total
Sep 3 - Sep 4
Total with taxes and fees
Berkshire Inn
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$158 nightly
$176 total
Sep 14 - Sep 15
Total with taxes and fees
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.
$129 nightly
$144 total
Sep 9 - Sep 10
Total with taxes and fees
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 bathroom with a white sink, mirror, and toilet.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$78 nightly
$87 total
Sep 3 - Sep 4
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A spacious living room with a fireplace, comfortable seating, and large windows.
A spacious living room with large windows, a fireplace, and a variety of seating options.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

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.
$106 nightly
$118 total
Sep 2 - Sep 3
Total with taxes and fees
Vacation Village in the Berkshires
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
A multi-story hotel with balconies, a pond with rocks, and a clear sky.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

10. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$135 nightly
$150 total
Aug 31 - Sep 1
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
Spa
4 stars
5 stars

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Price - quality =awesome"
Anastasia 3-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted 2 hours ago
The Red Lion Inn
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Clean comfortable; difficult to see sign locating property"
Doreen 1-night trip
Posted 3 hours ago
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 20 hours ago
Howard Johnson by Wyndham Lenox
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Excellent room super clean!"
Adriana 1-night trip
Posted 23 hours ago
Berkshire Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything was clean and well maintained. Very good included breakfast, close to Tanglewood, the Manor, the Norman Rockwell Museum, Lenox and Stockbridge."
Andrew 2-night trip
Posted 1 day ago
The Yankee Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
Frank 2-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. 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, Colonial Theater, and Barrington Stage Company. 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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