Pittsfield Hotels with Swimming Pool

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Check availability on Pittsfield Hotels with Swimming Pools

Our top choices for Pittsfield hotels with a pool

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, (1,005 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is RM398
RM444 total
includes taxes & fees
30 Jan - 31 Jan
Holiday Inn & 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, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is RM519
RM580 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (814 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is RM400
RM538 total
includes taxes & fees
1 Feb - 2 Feb
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
9.4 out of 10, Exceptional, (74 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is RM497
RM555 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841 reviews)
"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 RM349
RM390 total
includes taxes & fees
20 Jan - 21 Jan
Berkshire Inn
Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is RM564
RM630 total
includes taxes & fees
25 Jan - 26 Jan
Element Lenox Berkshires
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, (722 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is RM349
RM390 total
includes taxes & fees
21 Jan - 22 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, seasonal outdoor pool, pool loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is RM376
RM420 total
includes taxes & fees
26 Jan - 27 Jan
The Yankee, Trademark Collection by Wyndham
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (822 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is RM457
RM589 total
includes taxes & fees
21 Jan - 22 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (829 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is RM321
RM358 total
includes taxes & fees
20 Jan - 21 Jan
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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Top Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"As usual at the Yankee, check-in was friendly and quick. Room was clean and had everything in order. Rate was very reasonable.,"
Nathaniel 1-night trip
Posted 4 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. Best Western Plus Berkshire Hills Inn & Suites: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Hotel On North: Features a snack bar/deli, a pool and complimentary high-speed (wired) Internet access. Holiday Inn Express & Suites Pittsfield - Berkshires by IHG: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool and free self parking.
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.

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