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Find Hotels with a Pool in Pittsfield, MA from CA $125

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Check availability on Pittsfield Hotels with a Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Pittsfield hotels with a pool

An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with a counter, seating area, and large windows.

1. 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.
CA $141
CA $157 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
CA $121
CA $167 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
A hot tub with a tiled floor and a metal ladder.
A bathroom with a large mirror, a sink, and a towel rack.
Room
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

3. 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.
CA $146
CA $164 total
includes taxes & fees
Nov 13 - Nov 14
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 modern reception area with a green textured wall, a reception desk, and a coffee machine.

4. 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.
CA $182
CA $203 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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 hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.
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.
CA $122
CA $137 total
includes taxes & fees
Oct 20 - Oct 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
CA $140
CA $156 total
includes taxes & fees
Oct 25 - Oct 26
The Yankee Inn
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern bathroom with a bathtub, shower, and handrails.

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.
CA $156
CA $174 total
includes taxes & fees
Nov 12 - Nov 13
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

8. 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 centre.
CA $179
CA $200 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
CA $112
CA $125 total
includes taxes & fees
Oct 20 - Oct 21
Howard Johnson by Wyndham Lenox
Indoor pool
A spacious living room with a fireplace, comfortable seating, and large windows.
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.

10. 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.
CA $114
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Wonderful"
Philippe 2-night trip
Posted 6 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"good location, friendly helpful staff"
Scott Patterson 6-night trip
Posted 1 day ago
Quality Inn Great Barrington
Berkshire Inn

Berkshire Inn

10/10 Excellent
"This is an old motel-type one story place to stay, which I enjoyed. Rooms are large, clean and quiet. Comfortable bed, updated bathroom. No complaints."
Linda 1-night trip
Posted 5 days ago
Berkshire Inn

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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