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Pittsfield Hotels with Swimming Pool

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Check availability on Pittsfield Hotels with Swimming Pools

Tonight
4 Sept - 5 Sept
Tomorrow
5 Sept - 6 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Pittsfield hotels with a pool

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
RM322
RM450 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A pool area with a glass ceiling, multiple levels, and outdoor seating.
A multi-story hotel with a brick facade and a flat roof.
A lobby with three grey armchairs, a small round table with a plant, and a patterned rug.

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.
RM477
RM533 total
includes taxes & fees
7 Sept - 8 Sept
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 modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.
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.
RM477
RM533 total
includes taxes & fees
9 Sept - 10 Sept
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 bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
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.

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.
RM592
RM661 total
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn Lenox Pittsfield
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A motel with a parking lot, a swimming pool, and outdoor seating.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
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.
RM348
RM388 total
includes taxes & fees
1 Oct - 2 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 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.
RM421
RM470 total
includes taxes & fees
17 Sept - 18 Sept
The Yankee Inn
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

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.
RM487
RM544 total
includes taxes & fees
30 Sept - 1 Oct
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 hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
RM319
RM357 total
includes taxes & fees
7 Sept - 8 Sept
Howard Johnson by Wyndham Lenox
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
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.

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.
RM385
RM474 total
includes taxes & fees
15 Sept - 16 Sept
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 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.

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.
RM788
RM881 total
includes taxes & fees
15 Sept - 16 Sept
Element by Marriott Lenox 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
"The lounge was closed on Thursday. We went to a concert at Tanglewood and it would have been nice to have a nightcap. Might I suggest that you pole yiur guests and see if they are in town for a concert and if they would patronize the lounge if it was open."
Kenneth 1-night trip
Posted 9 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excellent customer service from front desk staff! Very nice decor everywhere. Fun little balcony! Quiet in the suite. All good!"
Leslieann H 1-night trip
Posted 10 hours ago
Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel was clean and stag was helpful and friendly."
Basil 2-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"this grand old hotel is warm and welcoming β€” a real hub of Bershires life and history"
James 2-night trip
Posted 2 days ago
The Red Lion Inn
Berkshire Inn

Berkshire Inn

8/10 Good
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
Ellen 1-night trip
Posted 2 days ago
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Clean comfortable; difficult to see sign locating property"
Doreen 1-night trip
Posted 13 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: Features a health club, an indoor pool and free valet parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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 high-speed (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, visit sights such as Berkshire Museum, Colonial Theater and Barrington Stage Company. 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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