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Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

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

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 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.
A spacious living room with a large sofa, a coffee table, and a fireplace.

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.
NT$4,084
NT$4,562 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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 reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

2. 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.
NT$3,162
NT$3,532 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
NT$2,738
NT$3,772 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Mountain Lodge
A swimming pool with a diving board and a hot tub area.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
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.
NT$3,130
NT$3,496 total
includes taxes & fees
Nov 6 - Nov 7
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 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.
NT$2,742
NT$3,063 total
includes taxes & fees
Oct 12 - Oct 13
Berkshire Inn
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel room with a large bed, wooden nightstands, a lamp, and a telephone.
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A modern bathroom with a wooden vanity, a toilet, and two 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.
NT$3,638
NT$4,063 total
includes taxes & fees
Nov 7 - Nov 8
Hampton Inn & Suites Berkshires-Lenox
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
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.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

7. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
NT$3,386
NT$3,782 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
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 restaurant with wooden flooring, bar area, and seating arrangements.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

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 center.
NT$4,012
NT$4,481 total
includes taxes & fees
Nov 1 - Nov 2
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 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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
NT$2,519
NT$2,814 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

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.
NT$4,567
NT$5,102 total
includes taxes & fees
Nov 8 - Nov 9
Element by Marriott Lenox Berkshires
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"it was beautiful, centrally located, perfect getaway"
Tara 1-night trip
Posted 12 hours ago
Hotel Downstreet, an Ascend Collection Hotel
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 2 days ago
The Yankee Inn
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 3 days ago
The Red Lion 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 4 days ago
Quality Inn Great Barrington

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. FairBridge Inn Express: Provides buffet, an indoor pool, and complimentary 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 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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