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Pittsfield Hotels with Swimming Pool

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Check availability on Pittsfield Hotels with Swimming Pools

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

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 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 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.
RM522
RM583 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
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.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
RM353
RM486 total
includes taxes & fees
12 Nov - 13 Nov
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 cafe with a counter, seating area, and large windows.
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.
RM388
RM433 total
includes taxes & fees
19 Nov - 20 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 motel with a parking lot, a swimming pool, and outdoor seating.
A bathroom with a bathtub, toilet, and shower.

4. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
RM351
RM392 total
includes taxes & fees
25 Oct - 26 Oct
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 freestanding bathtub, a fireplace, and two framed posters on the wall.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

5. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
RM433
RM483 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

6. 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.
RM448
RM500 total
includes taxes & fees
1 Nov - 2 Nov
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 modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
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.

7. 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.
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
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 bathroom with a white sink, mirror, and toilet.
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.
RM323
RM360 total
includes taxes & fees
25 Oct - 26 Oct
Howard Johnson by Wyndham 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 reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

9. 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.
RM551
RM616 total
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
Indoor pool
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.

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.
RM328
RM411 total
includes taxes & fees
1 Nov - 2 Nov
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 Yankee Inn

The Yankee Inn

8/10 Good
"Efficient & comfortable. Very good value."
brian 1-night trip
Posted 1 hour ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is hands down my favorite hotel, and I have stayed here before and will keep coming back again and again! Everything about this place makes it feel special. The rooms are always spotless, incredibly spacious, and equipped with everything you need to feel right at home. Having a coffee maker, a full-size refrigerator, an oven, and a stove makes such a difference, especially for longer stays. The excellent jacuzzi is another big plus and makes it easy to relax and unwind. The property also has so many great amenities, and the surrounding nature is absolutely beautiful. There are plenty of amazing places to explore nearby, making it a perfect destination for a relaxing getaway while still having lots of things to do. What I love most is that the rooms feel more like a fully equipped apartment than a typical hotel room. It’s the kind of place where you can truly settle in, feel comfortable, and wish you could stay longer. I absolutely love this hotel, and it will always be one of my favorite places to stay. I will definitely be back again and again!"
Diana 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Great stay"
barbara 1-night trip
Posted 6 hours ago
Comfort Inn & Suites East Greenbush - Albany
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Very clean room and apparently the room had been upgraded recently by real craftsmen. Well done. You don't expect this quality from an older motel, but the owners obviously take pride in the property."
Jeff 1-night trip
Posted 23 hours ago
Berkshire Inn
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 3 days ago
Hilton Garden Inn Lenox Pittsfield

Frequently asked questions

What are some accommodation options 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 high-speed (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 high-speed (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, visit sights such as Berkshire Museum, Colonial Theater and Bousquet Ski Area. The sporting events and theatre 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 the local weather in Pittsfield into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19Β°C, while the coldest months are January and February, with an average of -3Β°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 very many public transport options, so consider a car rental to maximise your time.

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