Hotels with Swimming Pool, Monterey Massachusetts

Q: What are some accommodations with pools in Monterey?

The Yankee Inn : Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge : Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold : Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn : Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG : Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.

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Our top choices for Monterey hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

P8,728 total

includes taxes & fees

Jul 7 - Jul 8

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

P4,643 total

includes taxes & fees

Jul 6 - Jul 7

Blackberry River Inn

Norfolk

Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.

P10,999 total

includes taxes & fees

Jul 5 - Jul 6

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.

P14,522 total

includes taxes & fees

Jul 16 - Jul 17

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.

P11,322 total

includes taxes & fees

Jul 27 - Jul 28

The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

P14,876 total

includes taxes & fees

Jul 22 - Jul 23

Desk, laptop workspace, iron/ironing board, free cribs/infant beds

The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

P7,685 total

includes taxes & fees

Jul 6 - Jul 7

Little Cat Lodge

Copake Falls

Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.

P10,487 total

includes taxes & fees

Jul 5 - Jul 6

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Choose what matters most at hotels with a pool in Monterey

Breakfast included

4 stars

Top Monterey Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Breakfast was great! We were caught off guard by the parking lot renovation but the free valet parking made up for it. Staff was very friendly! "

Quality Inn Great Barrington

10/10 Excellent

"I booked the stay at Quality Inn without knowing what to expect. Getting to the hotel was easy. The location was perfect with mountains all around. Comfortable bed and just right amenities made the stay enjoyable. The breakfast sitting area was separate from the hotel and had a cottage feel, enjoyed having breakfast. Exploring the town of Great Barrington was easy as everything was walking distance. Quality Inn is right next to Town Hall. Had a perfect view of the Strawberry moon sitting on the bench outside of the town hall. It was fun to see through the window of the Great Barrington fm radio station and chatting with the DJ hen he stepped out. A must to stop at SoCo ice-cream shop delicious cold treats. People are very friendly. The Pizza at The Great Barrington Pizza house was delicious. Walking around we could feel the history that has transpired, small town vibe, the architecture. Do not miss going to Great Barrington Farmers market, it is a co-op market and Guido's family owned super market."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved this place. It was a bit dated aesthetically, but the charm outweighed that. Beds are comfortable. The setting on the lake is beautiful and its size of the hotel is lovely. Staff and guests were delightful. In retrospect, I wish I’d paid more for a lakefront room — it would’ve been worth it. Hotel is centrally located and it’s easy to get everywhere. Only negative was that there was no recycling."