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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 3 - Oct 4
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Oct 4 - Oct 5
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Pittsfield hotels with a pool

Indoor pool
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.
A spacious living room with a fireplace, comfortable seating, and large windows.

1. 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.
$110 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$111 nightly
$124 total
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern cafe with a counter, seating area, and large windows.
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.
$99 nightly
$111 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A swimming pool with a diving board and a hot tub area.
Room
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

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.
$108 nightly
$121 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pool
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Exterior
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

5. 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.
$115 nightly
$129 total
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

6. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
  • Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
$151 nightly
$169 total
Nov 1 - Nov 2
Total with taxes and fees
Element by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
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.
A motel with a parking lot, a swimming pool, and outdoor seating.

7. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
$79 nightly
$88 total
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Inn
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.

8. 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.
$128 nightly
$143 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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.

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.
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
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.

10. 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
Oct 4 - Oct 5
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
Spa
4 stars
5 stars

Top Pittsfield Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"enjoyed our stay"
Mark 1-night trip
Posted 6 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."
Francesca 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel

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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