Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Tonight
7 May - 8 May
Tomorrow
8 May - 9 May
This weekend
8 May - 10 May
Next weekend
15 May - 17 May

Our top choices for Pittsfield hotels with a pool

Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is AED 322
AED 442 total
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (92 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is AED 481
AED 537 total
includes taxes & fees
13 May - 14 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (677 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is AED 496
AED 555 total
includes taxes & fees
13 May - 14 May
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (854 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is AED 282
AED 315 total
includes taxes & fees
25 May - 26 May
Berkshire Inn
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is AED 433
AED 484 total
includes taxes & fees
17 May - 18 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is AED 364
AED 406 total
includes taxes & fees
11 May - 12 May
The Yankee Inn
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (601 reviews)
  • cleanliness
    Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.
The price is AED 400
AED 447 total
includes taxes & fees
14 May - 15 May
Maple Terrace Motel
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is AED 404
AED 451 total
includes taxes & fees
10 May - 11 May
The Little Lion
Outdoor spa tub

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,350 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is AED 317
AED 394 total
includes taxes & fees
10 May - 11 May
Vacation Village in the Berkshires
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is AED 290
AED 324 total
includes taxes & fees
10 May - 11 May
Howard Johnson by Wyndham Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub

Top Pittsfield Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Excellent room and stay"
Audrey 1-night trip
Posted 4 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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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. Hotel On North: Provides a health club, an indoor pool, and free valet parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Best Western Plus Berkshire Hills Inn & Suites: Provides a snack bar/deli, a pool, and complimentary wired internet access.
What is there to see and do in Pittsfield?
Make a point to visit attractions like Housatonic River and Berkshire Museum. During your stay, check out sights such as Colonial Theater, Barrington Stage Company, 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.