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Hotels with Swimming Pool in Pittsfield, Massachusetts

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Check availability on Pittsfield Hotels with Swimming Pool

Next weekend
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19

Our top choices for Pittsfield hotels with a pool

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, (1,002 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is P7,814
P8,728 total
includes taxes & fees
Jul 6 - Jul 7
The Yankee Inn
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is P9,343
P10,464 total
includes taxes & fees
Jul 8 - Jul 9
Little Cat Lodge
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (783 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is P10,136
P11,322 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn Express Hotel & Suites Great Barrington 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, (687 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is P11,539
P12,889 total
includes taxes & fees
Jul 7 - Jul 8
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (120 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is P10,172
P11,363 total
includes taxes & fees
Jul 12 - Jul 13
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (871 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is P5,528
P6,175 total
includes taxes & fees
Jul 8 - Jul 9
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, (1,004 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is P9,337
P10,429 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is P8,209
P10,541 total
includes taxes & fees
Aug 4 - Aug 5
Berkshire Mountain Lodge
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,418 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is P8,450
P10,112 total
includes taxes & fees
Jul 12 - Jul 13
Vacation Village in the Berkshires
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
The price is P10,565
P11,801 total
includes taxes & fees
Jul 8 - Jul 9
Hotel Downstreet, an Ascend Collection Hotel
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Staff was very helpful particularly Jerry in outside cafe. Grounds keeper did a beautiful job! Outdoor pool was amazing! Will be back to swim in in the winter. Loved the shops located in the main building. We stayed in Maple Glen which was lovely. I was disappointed my room was dark but now know to ask for a sunnier room when booking."
Jayne 1-night trip
Posted 1 hour ago
The Red Lion Inn

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. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Offers buffet, an indoor pool, and complimentary wired internet access. Hotel On North: Features a health club, an indoor pool, and free valet parking. FairBridge Inn Express: Offers 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 wired internet access.
What is there to see and do in Pittsfield?
Surround yourself with nature at Housatonic River and Canoe Meadows Wildlife Sanctuary. During your stay, check out sights such as Berkshire Museum, Colonial Theater, and Barrington Stage Company. 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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