A historic building with classical architecture, a traffic light, and a yellow taxi.

Find Hotels with a Pool in Pittsfield, MA

Check availability on Pittsfield Hotels with a Pool

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Pittsfield hotels with a pool

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, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$109 nightly
$121 total
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
A hot tub area with a pool, lounge chairs, and a caution sign.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

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.
$107 nightly
$120 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
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.
$114 nightly
$127 total
Oct 22 - Oct 23
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-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 spacious living room with a large sofa, a coffee table, and a fireplace.
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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.
$146 nightly
$163 total
Sep 27 - Sep 28
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
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.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.

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.
$79 nightly
$88 total
Oct 25 - Oct 26
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 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.
$109 nightly
$122 total
Oct 25 - Oct 26
Total with taxes and fees
The Yankee Inn
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.

7. 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
Sep 27 - Sep 28
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

8. 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.
$125 nightly
$139 total
Sep 30 - Oct 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
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.
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.
$122 nightly
$136 total
Sep 27 - Sep 28
Total with taxes and fees
Vacation Village in the Berkshires
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.

10. 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.
$149 nightly
$167 total
Sep 28 - Sep 29
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Everything, delicious free breakfast, hot showers, plenty of room, outdoor patio w Adirondack chairs, pleasant staff, very clean place. Fabulous price! I would not hesitate to return to this place."
Joyce 2-night trip
Posted 5 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location; walkable to restaurants. Spacious 7th floor room had a nice town and mountain view. All staff friendly and helpful. Bed was comfortable; room very clean. Breakfast was minimal and uninspiring."
Karl 1-night trip
Posted 9 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Graham 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"It was clean spacious and staff was very nice"
Mary 1-night trip
Posted 2 days ago
Comfort Inn & Suites East Greenbush - Albany
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Good"
Michael 1-night trip
Posted 3 days ago
Berkshire Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Nice place, would stay again"
kaitlyn 1-night trip
Posted 9 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. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Offers buffet, an indoor pool, and complimentary wired internet access. FairBridge Inn Express: 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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