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
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 modern hotel lobby with seating areas, tables, and a reception desk.
A breakfast area with a counter, coffee machine, and a display of pastries.
A modern bathroom with a large mirror, a sink, and a shower.

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.
€93
includes taxes & fees
9 Nov - 10 Nov
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 hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A building with a porch and multiple windows, surrounded by purple flowers.
A living room with a sofa, armchair, coffee table, and a patterned rug.

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.
€134
includes taxes & fees
13 Oct - 14 Oct
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 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.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

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.
€143
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 two-story building with a gabled roof and a chimney.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

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.
€103
includes taxes & fees
1 Nov - 2 Nov
The Little Lion
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 large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
€201
includes taxes & fees
3 Nov - 4 Nov
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 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.

6. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
€89
includes taxes & fees
28 Oct - 29 Oct
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 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 room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

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.
€312
includes taxes & fees
5 Nov - 6 Nov
The Old Inn On The Green
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
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.

8. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
€106
includes taxes & fees
1 Nov - 2 Nov
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 outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
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.

9. 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 centre.
€125
includes taxes & fees
8 Nov - 9 Nov
Courtyard by Marriott Lenox Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A hotel room with a large bed, wooden nightstands, a lamp, and a telephone.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
€113
includes taxes & fees
7 Nov - 8 Nov
Hampton Inn & Suites Berkshires-Lenox
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
"Not enough bath clothes towels not enough outlets around the bed for people who have cpap or breathing problems."
Mark 1-night trip
Posted 1 day ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 2 days ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 3 days 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 9 days ago
Courtyard by Marriott Lenox Berkshires

Frequently asked questions

What are some accommodation options 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 swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Red Lion Inn: Offers buffet, an indoor pool and complimentary high-speed (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 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.