Photo by Photo courtesy of Berkshire Visitors Bureau

Find Hotels with a Pool in The Berkshires, MA

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Check availability on The Berkshires Hotels with a Pool

Top The Berkshires Hotels with a Pool

Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
  • Outdoor pool
  • Indoor pool
  • Pool umbrellas
8.8 out of 10, Excellent, (2133)
Mountain-view relaxation awaits at the indoor and outdoor pools after exploring Berkshire trails. Families appreciate the children's pool, playground, and game room, while skiers love the direct access to Jiminy Peak slopes.
The price is ￥15,266
￥18,743 total
includes taxes & fees
Nov 16 - Nov 17
Vacation Village in the Berkshires
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 ￥15,391
￥17,190 total
includes taxes & fees
Dec 7 - Dec 8
The Yankee, Trademark Collection by Wyndham
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, (952)
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 ￥13,588
￥15,177 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn & 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, (753)
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
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 ￥15,714
￥17,552 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2 indoor pools, 2 outdoor pools, pool umbrellas, sun 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
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (781)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is ￥20,833
￥25,423 total
includes taxes & fees
Nov 13 - Nov 14
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (586)
Sparkling waters welcome swimmers at the inviting indoor pool, complementing days spent exploring nearby Tanglewood Music Center and Kennedy Park. Staff members earn consistent praise for their attentive service at this comfortable Lenox retreat.
The price is ￥19,566
￥21,856 total
includes taxes & fees
Nov 23 - Nov 24
Courtyard by Marriott Lenox Berkshires
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (1002)
Sparkling waters invite refreshment at the outdoor pool, complemented by a rejuvenating hot tub that remains open year-round. Beyond aquatic pleasures, this historic hotel enchants with excellent dining, tasteful accommodations, and friendly service.
The price is ￥23,383
￥33,006 total
includes taxes & fees
Dec 9 - Dec 10
The Red Lion Inn
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 ￥17,131
￥19,135 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Lenox Pittsfield
Indoor pool, open 6:00 AM to 10 PM, sun loungers
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
  • Indoor pool
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (1002)
Refreshing waters await in the pristine indoor pool, complemented by a surprisingly warm hot tub for post-exploration relaxation. Stylish rooms with mountain views, a 24-hour fitness center, and peaceful ambiance create a rejuvenating retreat.
The price is ￥23,149
￥25,857 total
includes taxes & fees
Dec 8 - Dec 9
Hotel Downstreet, an Ascend Collection Hotel
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 The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Good "
Joy 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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