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Find Hotels with a Pool in Pittsfield, MA

Check availability on Pittsfield Hotels with a Pool

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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.
$108 nightly
$120 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 bathroom with a large mirror, a sink, and a towel rack.
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.
$115 nightly
$128 total
Oct 12 - Oct 13
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 spacious living room with a large sofa, a coffee table, and a fireplace.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

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.
$147 nightly
$164 total
Sep 20 - Sep 21
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

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.
$130 nightly
$145 total
Oct 13 - Oct 14
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 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.
$85 nightly
$95 total
Oct 13 - Oct 14
Total with taxes and fees
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.
$116 nightly
$130 total
Sep 22 - Sep 23
Total with taxes and fees
The Yankee Inn
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

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.
$134 nightly
$150 total
Sep 28 - Sep 29
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 bathroom with a white sink, mirror, and toilet.
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.

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
Sep 14 - Sep 15
Total with taxes and fees
Howard Johnson by Wyndham 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 14 - Sep 15
Total with taxes and fees
Vacation Village in the Berkshires
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

10. 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.
$178 nightly
$199 total
Sep 20 - Sep 21
Total with taxes and fees
Element by Marriott Lenox Berkshires
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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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My go-to place for visiting NW MA."
David 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

8/10 Good
"Beautiful views, friendly and responsive staff, property well kept. I would have given the highest praise except the indoor pool was closed for painting and maintenance. When I booked there was no notice in the website or Expedia. Since they had an outdoor pool and it was early fall, we swam theredes"
deb 2-night trip
Posted 7 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Outstanding customer service from Wylie, delicious food, coffee in lobby always available, superb housekeeping staff, quiet room, wide range of television channels including multiple HBO stations. We’re coming back!"
Ira 1-night trip
Posted 7 hours ago
Quality Inn Great Barrington
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Clean room, great location. Perfect base for a weekend in the Berkshires."
Alexandra 2-night trip
Posted 7 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Big rooms, nice shower pressure. Quiet at night. A great place to stay for enjoying the areas pleasures."
Jennifer 3-night trip
Posted 5 days ago
Hilton Garden Inn Lenox Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"Staff was helpful. Location close to Tanglewood. Bed and pillows were awesome. One elevator was not working so that was inconvenient"
April 1-night trip
Posted 8 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: Features a health club, an indoor pool, and free valet parking. Hotel On North: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. 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 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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