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

Hotels with Swimming Pool in Monterey, Massachusetts

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Check availability on Monterey Hotels with Swimming Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Monterey hotels with a pool

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.

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.
P8,986
P10,037 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 breakfast area with a counter, coffee machine, and a display of pastries.
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.
P5,942
P6,638 total
includes taxes & fees
Nov 2 - Nov 3
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 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.

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.
P6,981
P9,021 total
includes taxes & fees
Oct 8 - Oct 9
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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.

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.
P18,140
P21,889 total
includes taxes & fees
Nov 1 - Nov 2
The Old Inn On The Green
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.
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.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,853
P14,114 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
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.

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.
P6,474
P7,232 total
includes taxes & fees
Oct 18 - Oct 19
The Little Lion
A swimming pool with lounge chairs, surrounded by trees and a small building.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A large, two-story house with a well-maintained lawn and a fence.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

7. 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.
P23,082
P25,782 total
includes taxes & fees
Nov 2 - Nov 3
Devonfield Inn B&B
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
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.

8. 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.
P7,857
P8,776 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott 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 modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

9. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P6,631
P7,406 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
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.

10. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
P5,264
P5,880 total
includes taxes & fees
Oct 6 - Oct 7
Sunset Inn
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 2 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The cleaning staff were friendly and helpful!"
Mayra 2-night trip
Posted 17 hours ago
Quality Inn Great Barrington
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"I was only there to sleep for a few hours"
Thomas 1-night trip
Posted 6 days ago
Courtyard by Marriott Lenox Berkshires

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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