Photo by Photo courtesy of Berkshire Visitors Bureau

Find Hotels with a Pool in The Berkshires, MA

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Our top choices for The Berkshires hotels with a pool

1. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$113 nightly
The price is $126
Nov 15 - Nov 16
Total with taxes and fees
The Yankee Inn

2. 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, (857 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
$83 nightly
The price is $93
Dec 10 - Dec 11
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,268 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$111 nightly
The price is $124
Dec 6 - Dec 7
Total with taxes and fees
Berkshire Mountain Lodge

4. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (690 reviews)
  • cleanliness
    Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
$126 nightly
The price is $140
Nov 29 - Nov 30
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires

5. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$135 nightly
The price is $150
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

6. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
$110 nightly
The price is $122
Nov 18 - Nov 19
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (718 reviews)
  • cleanliness
    Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

8. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,840 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
$108 nightly
The price is $121
Nov 17 - Nov 18
Total with taxes and fees
Vacation Village in the Berkshires

9. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,015 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$197 nightly
The price is $220
Nov 29 - Nov 30
Total with taxes and fees
The Red Lion Inn

10. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (822 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
$161 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington 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.

Choose what matters most at hotels with a pool in The Berkshires

Top The Berkshires Hotel Reviews

Find out more about The Berkshires

Discover top The Berkshires attractions

The Berkshires is a treasure trove of unique experiences that will captivate travelers seeking both adventure and culture. Begin your exploration at the stunning natural landscapes of the nearby mountains, where opportunities for engaging in outdoor activities abound, from picturesque hiking paths to tranquil picnicking spots that allow for family bonding amidst nature. Art enthusiasts will appreciate the rich cultural offerings, including a range of galleries showcasing regional artists and acclaimed exhibitions, allowing for a deep dive into the local artistic scene. If you're in the mood for a bit of history, the charming small towns are dotted with historic sites that tell the story of the region's past, perfect for leisurely strolls and family outings. For a memorable evening, consider attending an outdoor concert or performance under the stars, where you can enjoy world-class music in a beautiful setting. Lastly, don’t miss the opportunity to sample locally crafted foods and artisanal products at nearby markets, providing a taste of the Berkshires’ culinary delights. After a day of exploration, unwind in one of the area’s boutique accommodations, where attentive service and thoughtful amenities ensure a comfortable and pampered stay.

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