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Hotels with Swimming Pools in Pittsfield

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Check availability on Pittsfield Hotels with Swimming Pools

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
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.

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.
S$182
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.
S$155
includes taxes & fees
8 Nov - 9 Nov
Berkshire Mountain Lodge
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
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.

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.
S$147
includes taxes & fees
5 Nov - 6 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A swimming pool with a diving board and a hot tub area.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A bathroom with a large mirror, a sink, and a towel rack.
Room

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.
S$140
includes taxes & fees
7 Nov - 8 Nov
Holiday Inn & Suites Pittsfield-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 bathroom with a bathtub, toilet, and shower.

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.
S$116
includes taxes & fees
8 Nov - 9 Nov
Berkshire Inn
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
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.
S$151
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 hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
A modern bathroom with a white bathtub, a showerhead, and a towel rack.
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.
S$163
includes taxes & fees
7 Nov - 8 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 covered outdoor area with stone pillars and a view of a road and green hills.
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.

8. 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.
S$179
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox 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 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.
S$204
includes taxes & fees
8 Nov - 9 Nov
Element 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 hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
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.
S$113
includes taxes & fees
18 Oct - 19 Oct
Howard Johnson by Wyndham Lenox
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

10/10 Excellent
"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."
Mark 1-night trip
Posted 16 hours ago
The Yankee Inn
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Clean room. Plenty of parking. Convenient breakfast"
Mateo 1-night trip
Posted 1 day ago
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"
Rohit 1-night trip
Posted 2 days ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great stay, very clean, super comfortable beds. Will def stay again when in the area."
Julia 2-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 2 days ago
The Red Lion Inn
Berkshire Inn

Berkshire Inn

10/10 Excellent
"We stayed one night after a concert at Tanglewood, and the hotel was perfectly fine for our purpose: clean and comfortable."
Mare 1-night trip
Posted 3 days ago
Berkshire Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 3 days ago
Quality Inn Great Barrington

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 19°C, while the coldest months are January and February, with an average of -3°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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