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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 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

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 hotel lobby with a snow-covered entrance and a sign reading "Lobby".
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 Holiday Inn & Suites hotel with a modern design, featuring a prominent sign and a well-lit entrance.
A banquet hall with round tables set for a formal event, featuring white tablecloths, silverware, and floral centerpieces.

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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.

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 modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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 14 - Sep 15
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 hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.

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.
$90 nightly
$101 total
Aug 24 - Aug 25
Total with taxes and fees
Berkshire Inn
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

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 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 14 - Sep 15
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 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 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.
$79 nightly
$88 total
Aug 31 - Sep 1
Total with taxes and fees
Howard Johnson by Wyndham Lenox
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with a fireplace, comfortable seating, and 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 3 - Sep 4
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 serene riverside view with a stone bridge, reflecting trees and buildings.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.

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

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 7 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 18 hours ago
The Yankee Inn
Berkshire Inn

Berkshire Inn

8/10 Good
"Hotels in the Lenox area are dramatically over-priced this time of year (Tanglewood, I trust). Berkshire Inn was the one with a bit more reasonable price and a good rating. We were pleased to find that the rooms were just as pictured... clean, neat and must have had a recent (very attractive) renovation. Very comfortable overnight stay in a motel with almost no amenities, friendly gentleman in the office and, while still over-priced, not quite at the extreme level of all other area options."
Pamela 1-night trip
Posted 22 hours ago
Berkshire Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."
Linda 1-night trip
Posted 4 days 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: Offers 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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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 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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