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

Monterey Hotel Guide - Hotels with Pool in Monterey, Massachusetts

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Check availability on Monterey Hotels with Pool

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Monterey hotels with a pool

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.
A modern hotel lobby with seating areas, tables, and a reception desk.
A buffet with labeled containers for omelets and other dishes.
A hotel room with two beds, a desk, a TV, and a window with curtains.

1. 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.
€118
includes taxes & fees
23 Sept - 24 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A multi-story hotel with balconies, a pond with rocks, and a clear sky.

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
€129
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort
A large house with a balcony and a grassy yard.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A two-story building with a gabled roof and a chimney.

3. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
€108
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
A backyard with a swimming pool, lounge chairs, and a hot tub.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A covered porch with wicker furniture and hanging flower baskets.

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
€193
includes taxes & fees
8 Sept - 9 Sept
The Red Lion Inn
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
A hotel room with two beds, a desk, a television, and a dresser.

5. 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.
€186
includes taxes & fees
30 Aug - 31 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
€151
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

7. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
€93
includes taxes & fees
26 Aug - 27 Aug
Sunset Inn
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.
A spacious lobby with a fireplace, seating area, and a bar.

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
€110
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A white two-story house with a front door, windows, and a chimney.

9. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
  • Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
€329
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
€76
includes taxes & fees
31 Aug - 1 Sept
Howard Johnson by Wyndham Lenox
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Choose what matters most at hotels with a pool in Monterey

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Monterey Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"If you're looking for a nice basic hotel with breakfast and free parking, I highly recommend this Quality Inn in Great Barrington, MA. Our room was clean, comfortable, and well priced. Breakfast included a nice variety of hot and cold food items. The scrambled eggs and sausage links were very tasty, and so were the make-your-own waffles. The staff were very nice. I look forward to returning. Note: A freight rail line runs through Great Barrington once a day."
Roberta 1-night trip
Posted less than an hour ago
Quality Inn Great Barrington
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 2 days ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 3 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What are some accommodation options with pools in Monterey?
Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay: Offers a seasonal outdoor pool, an indoor pool and buffet. The Yankee Inn: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshires Untold: Offers 3 restaurants, an outdoor pool and spa services. FairBridge Inn Express: Features free self parking, an outdoor pool and flat-screen televisions.
What is there to see and do in Monterey?
Spend some time experiencing the great outdoors at Lake Garfield and Bidwell House Museum. Discover sights such as Mount Wilcox during your stay.
When is the best time to book a hotel with a pool in Monterey?
Taking the local weather in Monterey into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Monterey are January, March, February and November, with each month seeing an average of 18 cm of snowfall.