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Find Hotels with a Pool in The Berkshires, MA

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Check availability on The Berkshires Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for The Berkshires hotels with a pool

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$101 nightly
$112 total
Nov 1 - Nov 2
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
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
$90 nightly
$101 total
Nov 12 - Nov 13
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$110 nightly
$123 total
Nov 23 - Nov 24
Total with taxes and fees
Berkshire Mountain Lodge

4. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
$110 nightly
$122 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$135 nightly
$150 total
Oct 26 - Oct 27
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

6. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires

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

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
$144 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

8. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
  • Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
$119 nightly
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

9. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$191 nightly
$214 total
Nov 8 - Nov 9
Total with taxes and fees
The Red Lion Inn

10. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
$117 nightly
$131 total
Nov 23 - Nov 24
Total with taxes and fees
Vacation Village in the Berkshires
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Choose what matters most at hotels with a pool in The Berkshires

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in The Berkshires

The Yankee Inn

The Yankee Inn
Lenox
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
$144 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
$135 nightly
$150 total
Oct 26 - Oct 27
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
$119 nightly
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
$90 nightly
$101 total
Nov 12 - Nov 13
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
$110 nightly
$122 total
Oct 30 - Oct 31
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
$135 nightly
$151 total
Nov 8 - Nov 9
Total with taxes and fees
Element by Marriott Lenox Berkshires

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
$79 nightly
$88 total
Oct 25 - Oct 26
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
$119 nightly
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
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4-star hotels with pools in The Berkshires

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
$393 nightly
$439 total
Nov 7 - Nov 8
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
$383 nightly
$428 total
Nov 12 - Nov 13
Total with taxes and fees
The Inn at Stockbridge

Devonfield Inn B&B

Devonfield Inn B&B
Lee
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B

Hampton Terrace Inn

Hampton Terrace Inn
Lenox
$219 nightly
$245 total
Nov 18 - Nov 19
Total with taxes and fees
Hampton Terrace Inn

The Old Inn On The Green

The Old Inn On The Green
Great Barrington
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
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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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.

Top The Berkshires Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."
Marcia 1-night trip
Posted 6 hours ago
Hampton Inn & Suites Berkshires-Lenox
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Very easy check in. Clean and safe."
James Kevin 3-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."
Joan 2-night trip
Posted 11 hours ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Forgot the woman’s name who checked us in but she was so helpful and friendly with awesome dinner suggestions. Locations was great to walk around town"
Monica 2-night trip
Posted 11 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."
Denise 1-night trip
Posted 12 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"
carole 1-night trip
Posted 16 hours ago
The Red Lion Inn

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