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Check availability on Pittsfield Hotels with a Pool

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16

Our top choices for Pittsfield hotels with a pool

Indoor pool

1. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,006 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is ￥18,731
￥20,922 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool

2. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (698 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is ￥30,265
￥33,806 total
includes taxes & fees
Aug 23 - Aug 24
Hilton Garden Inn Lenox Pittsfield
Indoor pool

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,037 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is ￥17,482
￥23,043 total
includes taxes & fees
Sep 2 - Sep 3
Berkshire Mountain Lodge
Indoor pool

4. 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, (148 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is ￥23,138
￥25,845 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Seasonal outdoor pool

5. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (901 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is ￥12,896
￥14,405 total
includes taxes & fees
Aug 11 - Aug 12
Berkshire Inn
View from room

6. 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 ￥25,924
￥28,958 total
includes taxes & fees
Aug 3 - Aug 4
The Yankee Inn
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

7. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is ￥25,685
￥28,690 total
includes taxes & fees
Aug 26 - Aug 27
Hampton Inn & Suites Berkshires-Lenox
Indoor pool

8. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (643 reviews)
  • cleanliness
    Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
The price is ￥34,652
￥38,707 total
includes taxes & fees
Aug 13 - Aug 14
Courtyard by Marriott Lenox Berkshires
Indoor pool, outdoor pool, pool umbrellas

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,490 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is ￥17,174
￥20,911 total
includes taxes & fees
Aug 12 - Aug 13
Vacation Village in the Berkshires
Indoor pool

10. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (31 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is ￥36,045
￥40,263 total
includes taxes & fees
Aug 13 - Aug 14
Element by Marriott Lenox Berkshires
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
"Be aware it’s an old inn; that being said it’s charming."
Jonathan 4-night trip
Posted 11 hours 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. FairBridge Inn Express: Offers a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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 Pontoosuc Lake and Housatonic River. 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.