Hotels with Swimming Pool in Pittsfield, Massachusetts

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Swimming Pool

Top Pittsfield Hotels with Swimming Pool

Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (950)
Swimmers splash in the pristine indoor pool from 7 AM to 9 PM, complemented by an on-site health club for complete wellness. Hiking trails and skiing opportunities nearby make this centrally located hotel an ideal family-friendly retreat.
The price is P5,200
P5,808 total
includes taxes & fees
Nov 14 - Nov 15
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.4 out of 10, Exceptional, (57)
Plunge into the indoor pool open from 8:00 AM to 10:00 PM after exploring nearby Tanglewood Music Center. Soothing hot tub sessions complement winter activities like cross-country skiing, while attentive staff ensure a refreshingly clean, well-maintained aquatic retreat.
The price is P6,966
P7,781 total
includes taxes & fees
Dec 2 - Dec 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (752)
Plunge into the pristine indoor pool after exploring hiking trails or nearby Tanglewood Music Center. Sun loungers invite relaxation while the hot tub soothes tired muscles. Beyond aquatic pleasures, this lodge offers fitness facilities and an arcade room.
Berkshire Mountain Lodge
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
  • Indoor pool
9.2 out of 10, Wonderful, (656)
Sparkling waters await in the pristine indoor swimming pool, complemented by a modern fitness center for complete rejuvenation. Nearby Tanglewood Music Center offers cultural enrichment, while Jae's Asian Fusion restaurant provides delicious dining options.
The price is P6,556
P7,323 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
7.8 out of 10, Good, (837)
Seasonal outdoor pool beckons sun-seekers from June through August at this spotless, centrally located motel. After a day of skiing or downtown exploration, guests appreciate comfortable beds, updated rooms with refrigerators, and friendly service.
The price is P4,716
P5,268 total
includes taxes & fees
Nov 23 - Nov 24
Berkshire Inn
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.6 out of 10, Exceptional, (10)
Swimming enthusiasts appreciate the serene indoor pool that provides year-round aquatic enjoyment regardless of weather. After energizing laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is P7,959
P8,890 total
includes taxes & fees
Nov 20 - Nov 21
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
  • Indoor pool
8.8 out of 10, Excellent, (692)
Splash into the warm, pristine indoor pool after exploring nearby hiking trails or skiing at Butternut. Modern rooms with premium bedding await, while a complimentary breakfast buffet energizes adventures in Great Barrington's vibrant surroundings.
The price is P6,308
P7,046 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1002)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendor. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is P5,963
P6,661 total
includes taxes & fees
Nov 19 - Nov 20
The Yankee, Trademark Collection by Wyndham
Exterior
Cozy Corner Motel

Cozy Corner Motel

2.0 star property
Williamstown
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Business services
9.2 out of 10, Wonderful, (881)
Families splash in the lazy river while adventure seekers prepare for nearby hiking trails and cross-country skiing. This family-run motel balances aquatic fun with mountain recreation, creating perfect days that end with sunset barbecues in the garden.
The price is P4,404
P5,199 total
includes taxes & fees
Nov 13 - Nov 14
Cozy Corner Motel
Seasonal outdoor pool
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
  • Pool
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Microwave
9.2 out of 10, Wonderful, (85)
Surrounded by mountain views, the seasonal outdoor pool offers summer relaxation with comfortable lounge chairs and hangout spots. Guests love the well-appointed rooms, friendly staff, and outdoor entertainment areas featuring firepits and charcoal grills.
The price is P6,409
P7,030 total
includes taxes & fees
Nov 13 - Nov 14
The Springs Motel
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

Top Pittsfield Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Everything was great"
Theresa 2-night trip
Posted 3 days ago
Comfort Inn & Suites East Greenbush - Albany

Explore a world of travel with Expedia

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 & Suites Pittsfield-Berkshires by IHG: Offers a health club, an indoor pool, and complimentary wired internet access. Hotel On North: Features buffet, an indoor pool, and complimentary wired internet access. FairBridge Inn Express: Offers a snack bar/deli, a pool, and complimentary wired internet access. Best Western Plus Berkshire Hills Inn & Suites: Provides 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 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.