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

Find Hotels with a Pool in Monterey, MA

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Check availability on Monterey Hotels with a Pool

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Oct 3 - Oct 4
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Oct 4 - Oct 5
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Monterey hotels with a pool

An indoor swimming pool with clear lane markings, a poolside area with lounge chairs, and large windows allowing natural light.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with seating areas, tables, and a reception desk.

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.
$95 nightly
$106 total
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

2. 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.
$129 nightly
$144 total
Oct 6 - Oct 7
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
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.
A hotel room with two beds, a desk, a television, and a dresser.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

3. 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.
$144 nightly
$160 total
Nov 2 - Nov 3
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A large house with a balcony and a grassy yard.
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.
A bathroom with a toilet, a shower with glass doors, and a towel rack with towels.

4. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
$115 nightly
$128 total
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
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.
$192 nightly
$215 total
Nov 2 - Nov 3
Total with taxes and fees
The Red Lion Inn
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A hotel room with two beds, a chair, and a bedside table with a phone.

6. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
$77 nightly
$86 total
Oct 6 - Oct 7
Total with taxes and fees
Sunset Inn
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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.
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.

7. 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.
$319 nightly
$350 total
Nov 1 - Nov 2
Total with taxes and fees
The Old Inn On The Green
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

8. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
$140 nightly
$161 total
Oct 28 - Oct 29
Total with taxes and fees
Blackberry River Inn
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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

9. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$106 nightly
$118 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A covered outdoor area with stone pillars and a view of a road and green hills.

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
View all properties

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 Yankee Inn

The Yankee Inn

10/10 Excellent
"I can’t say enough about the care we received at the Yankee Inn. We stayed one night on the second day of a two-week tour of the Northeast. The room was clean and well equipped, the beds and pillows were comfortable, and breakfast included eggs, sausage, and a waffle maker. But what truly stood out was the care and concern George at the front desk showed us. Just after we checked out, the check engine light and several other warning lights came on in our two-month-old Subaru. I hoped Subaru could provide a quick diagnosis, but the only help they offered was a tow to the nearest dealership. We had no idea what to do. If the dealership had to keep the car for diagnosis, we could be stranded for days. When we asked George whether a room would be available if we needed to stay another night, he said the hotel had only one left. Because we still didn’t know what would happen with the car, he offered to hold it until we knew whether we needed it. He also opened the lounge so we could store the luggage we had to remove before the car was towed. He made us feel welcome and went out of his way to help in every way he could. Fortunately, the dealership identified the problem, and we drove away that afternoon to continue our trip. The room and breakfast were great, but the Yankee Inn’s extraordinary kindness is what would bring us back!"
John 1-night trip
Posted 1 hour ago
The Yankee Inn

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.

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