Hotels with Swimming Pools in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Swimming Pools

This weekend
Next weekend

Top Hotels with Swimming Pools in Pittsfield

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (60)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is S$139
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (970)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is S$130
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (765)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
The price is S$165
includes taxes & fees
9 Dec - 10 Dec
Berkshire Mountain Lodge

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is S$162
includes taxes & fees
14 Dec - 15 Dec
Hilton Garden Inn Lenox Pittsfield

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (839)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is S$119
includes taxes & fees
27 Nov - 28 Nov
Berkshire Inn

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is S$190
includes taxes & fees
14 Dec - 15 Dec
Element Lenox Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1007)
"Great stay!"
United States
Ann
The price is S$91
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (698)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is S$156
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2148)
"Great place!"
United States
Nicole
The price is S$122
includes taxes & fees
29 Nov - 30 Nov
Vacation Village in the Berkshires

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1009)
"Staff was very nice!"
United States
David
The price is S$156
includes taxes & fees
20 Dec - 21 Dec
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.

Black Friday Sale

Save up to 50% on select hotels

Top Pittsfield Hotel Reviews

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. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. Hotel On North: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Best Western Plus Berkshire Hills Inn & Suites: Features a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Provides free self parking, a seasonal outdoor pool and complimentary wireless 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, 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.