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Find Hotels with a Pool in Monterey, MA

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Check availability on Monterey Hotels with a Pool

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Monterey hotels with a pool

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

1. 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.
AED 528
AED 589 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
A modern hotel lobby with seating areas, tables, and a reception desk.

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.
AED 331
AED 369 total
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A multi-story building with a symmetrical facade, multiple balconies, and a central tower.
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

3. 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.
AED 430
AED 552 total
includes taxes & fees
28 Oct - 29 Oct
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A white two-story house with a front door, windows, and a chimney.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

4. 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.
AED 1,065
AED 1,285 total
includes taxes & fees
1 Nov - 2 Nov
The Old Inn On The Green
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
AED 579
AED 829 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

6. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
AED 380
AED 425 total
includes taxes & fees
28 Oct - 29 Oct
The Little Lion
A backyard with a swimming pool, surrounded by grass and trees.
Exterior
A stone fountain surrounded by trees in a park setting.
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

7. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
AED 1,340
AED 1,571 total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A large, two-story house with a well-maintained lawn and a fence.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

8. Devonfield Inn B&B

Devonfield Inn B&B
Lee
  • Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.
AED 1,355
AED 1,514 total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A hotel room with two beds, a chair, and a bedside table with a phone.

9. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
AED 298
AED 332 total
includes taxes & fees
1 Nov - 2 Nov
Sunset Inn
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A grand hallway with a chandelier, a staircase, and a table with flowers.
A room with a fireplace, two striped armchairs, and a floral drape.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

10. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
AED 656
AED 754 total
includes taxes & fees
27 Oct - 28 Oct
Blackberry River Inn
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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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Room was very clean and updated. We enjoyed the deck, although it needs some updating due to broken boards. I was told the restaurant was a fine place to dine. Desk staff was helpful."
Barbara 2-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"We love staying at this hotel every fall. It is in an easy access location with plenty of parking and very clean. The staff are very friendly and the breakfast is fantastic. We’ll be back!!"
Patricia 2-night trip
Posted 17 hours ago
Quality Inn Great Barrington

Frequently asked questions

What are some accommodations with pools in Monterey?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Quality Inn Great Barrington: Provides a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Offers buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in Monterey?
Spend some time experiencing the great outdoors at Lake Garfield and Mount Wilcox. 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.