Hotels with Pool & Resorts in Pittsfield from NZ$129

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Pool

Tonight
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

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, (850 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NZ$250
includes taxes & fees
23 Feb - 24 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
9.2 out of 10, Wonderful, (83 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is NZ$247
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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)
"Staff was very courteous and rooms clean."
United States
Steven
The price is NZ$193
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (844 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 NZ$155
includes taxes & fees
2 Mar - 3 Mar
Berkshire Inn
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (667 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is NZ$256
includes taxes & fees
27 Feb - 28 Feb
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NZ$260
includes taxes & fees
2 Mar - 3 Mar
Element Lenox Berkshires
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is NZ$129
includes taxes & fees
23 Feb - 24 Feb
Howard Johnson by Wyndham Lenox
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (596 reviews)
"Cute place"
United States
Lisa
The price is NZ$185
includes taxes & fees
22 Feb - 23 Feb
Maple Terrace Motel
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, (1,009 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NZ$173
includes taxes & fees
2 Mar - 3 Mar
The Yankee, Trademark Collection by Wyndham
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, (736 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is NZ$193
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Spa pool

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"The room was fresh, recent renovation was done with attention to detail. Breakfast was great. The only thing I can say bad is the coffee was awful"
Anthony 1-night trip
Posted 3 days ago
Comfort Inn & Suites East Greenbush - Albany

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: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Pittsfield?
Make a point to visit attractions such as Housatonic River and Berkshire Museum. During your stay, visit sights such as Colonial Theater, Bousquet Ski Area and Hancock Shaker Village. 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.