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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
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Pittsfield hotels with a pool

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern reception area with a green textured wall, a reception desk, and a coffee machine.
A hotel patio with outdoor seating and a fire pit.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

1. 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.
₩170,215
₩190,128 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩115,453
₩158,768 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
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 hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

3. 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.
₩126,754
₩141,584 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
An indoor swimming pool with multiple lanes, seating areas, and safety railings.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
Room
A bathroom with a large mirror, a sink, and a towel rack.

4. 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.
₩137,098
₩153,137 total
includes taxes & fees
Nov 20 - Nov 21
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A bathroom with a bathtub, toilet, and shower.
A hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.
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.
₩114,457
₩127,848 total
includes taxes & fees
Oct 25 - Oct 26
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 glass-enclosed shower, a toilet, and a towel rack.
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.
₩141,091
₩157,600 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A modern bathroom with a white bathtub, a showerhead, and a towel rack.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.

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.
₩145,950
₩163,026 total
includes taxes & fees
Nov 3 - Nov 4
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.
₩105,153
₩117,456 total
includes taxes & fees
Nov 3 - Nov 4
Howard Johnson by Wyndham Lenox
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 large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

9. 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.
₩167,193
₩186,754 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Lenox Berkshires
Indoor pool
A spacious living room with large windows, a fireplace, and a variety of seating options.
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.

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.
₩106,939
₩134,052 total
includes taxes & fees
Nov 11 - Nov 12
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

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Lovely stay!"
Nora 1-night trip
Posted 9 hours ago
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Amazing experience, Great for families,nearby many trails and scenic driveway! Will be back certainly"
Chui shan 1-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Nice people, ok and clean room. Too much light from around the window shades and all the gizmos (thermostat, TV etc.) to the point of inhibiting sleep."
Graydon 2-night trip
Posted 1 day ago
Hilton Garden Inn Lenox Pittsfield
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Would stay here again for sure"
Jennifer 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
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 9 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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