Hotels with Swimming Pool in Monterey, Massachusetts

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Check availability on Monterey Hotels with Swimming Pool

Our top choices for Monterey hotels with a pool

Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (180 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is P9,610
P11,052 total
includes taxes & fees
May 27 - May 28
Blackberry River Inn
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is P6,729
P7,516 total
includes taxes & fees
May 27 - May 28
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (940 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is P5,415
P7,428 total
includes taxes & fees
May 24 - May 25
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
8.8 out of 10, Excellent, (765 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is P7,963
P8,895 total
includes taxes & fees
Jun 1 - Jun 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (854 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is P4,876
P5,446 total
includes taxes & fees
May 28 - May 29
Howard Johnson by Wyndham Lenox
Indoor pool

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, (780 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is P10,442
P11,664 total
includes taxes & fees
May 25 - May 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is P8,049
P8,990 total
includes taxes & fees
May 26 - May 27
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is P4,937
P5,515 total
includes taxes & fees
May 28 - May 29
Berkshire Inn
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is P7,031
P7,854 total
includes taxes & fees
May 21 - May 22
Holiday Inn & Suites Pittsfield-Berkshires 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
9.2 out of 10, Wonderful, (897 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is P7,166
P9,211 total
includes taxes & fees
May 28 - May 29
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 Monterey

Breakfast included
4 stars

Top Monterey Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"We enjoyed our stay at the Black Swan and sitting on our balcony with a view of the lake. "
Susan 3-night trip
Posted 1 hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What are some accommodations with pools in Monterey?
Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Features 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Offers buffet, an indoor pool, and complimentary wired internet access. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Hotel located near Tanglewood Music Center. Offers a snack bar/deli, an indoor pool, and free self parking.
What is there to see and do in Monterey?
Make a point to visit attractions like Iroquis Waterfront and Mahaiwe Performing Arts Center. Discover sights such as Bidwell House Museum during your stay.
When is the best time to book a hotel with a pool in Monterey?
Taking into account the local weather in Monterey 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 28°F. The snowiest months in Monterey are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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