The Best Hotels with a Pool in Monterey, MA from NT$2,433 in 2026

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.

A lake surrounded by autumn-colored trees reflecting on the water.

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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.

NT$5,609 total

includes taxes & fees

Jul 27 - Jul 28

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.

NT$5,673 total

includes taxes & fees

Jul 30 - Jul 31

Little Cat Lodge

Copake Falls

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

NT$7,952 total

includes taxes & fees

Jul 21 - Jul 22

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.

NT$7,001 total

includes taxes & fees

Aug 13 - Aug 14

The Red Lion Inn

Stockbridge

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

NT$7,568 total

includes taxes & fees

Jul 22 - Jul 23

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

NT$7,578 total

includes taxes & fees

Jul 19 - Jul 20

M3 Romantic Suite | Living area | 43-inch LCD TV with digital channels, streaming services

Blackberry River Inn

Norfolk

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

NT$5,764 total

includes taxes & fees

Jul 19 - Jul 20

Berkshire Travel Lodge

Austerlitz

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

NT$2,433 total

includes taxes & fees

Jul 15 - Jul 16

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Choose what matters most at hotels with a pool in Monterey

Breakfast included

4 stars

Top Monterey Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Comfortable rooms within walking distance to Great Barrington."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem a little tired, but the room was very good value - especially as we overlooked the lake. The location is wonderful for Lee, Lenox, Stockbridge, all the cultural centers and the Mass Pike. A beach is adjacent for swimming. We plan to return next year."

Frequently asked questions

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.

What is there to see and do in Monterey?

Spend some time experiencing the great outdoors at Lake Garfield. 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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