A large stone church with a tall bell tower and arched windows.

Hotels with Swimming Pool in Great Barrington, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Great Barrington Hotels with Swimming Pool

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Great Barrington hotels with a pool

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 Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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.
P9,016
P10,071 total
includes taxes & fees
Nov 4 - Nov 5
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 modern hotel lobby with seating areas, tables, and a reception desk.
A modern bathroom with a large mirror, a sink, and a shower.
A breakfast area with a counter, coffee machine, and a display of pastries.

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.
P6,214
P6,941 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A poolside area with lounge chairs and a pool.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

3. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
P19,492
P23,876 total
includes taxes & fees
Nov 2 - Nov 3
Prospect Berkshires
A large house with a balcony and a grassy yard.
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.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

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.
P6,496
P7,256 total
includes taxes & fees
Nov 4 - Nov 5
The Little Lion
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 a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A white two-story house with a front door, windows, and a chimney.

5. 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.
P18,201
P21,963 total
includes taxes & fees
Nov 5 - Nov 6
The Old Inn On The Green
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 living room with a sofa, armchair, coffee table, and a patterned rug.
A building with a porch and multiple windows, surrounded by purple flowers.

6. 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.
P7,343
P9,430 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n' Spruce Resort in the 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.

7. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P6,654
P7,433 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.
A house with a stone patio and wooden stools.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.

8. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
P9,546
P10,692 total
includes taxes & fees
Nov 2 - Nov 3
Little Cat Lodge
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 modern restaurant with wooden flooring, bar area, and seating arrangements.

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 center.
P7,884
P8,806 total
includes taxes & fees
Nov 5 - Nov 6
Courtyard by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,886
P14,161 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
View all properties

Choose what matters most at hotels with a pool in Great Barrington

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Great Barrington 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 3 hours ago
The Yankee Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Clean room, very friendly and accommodating staff and free parking"
Alana 2-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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 1 day ago
The Red Lion Inn
Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Super clean and cozy and safe"
Andrea 1-night trip
Posted 2 days ago
Monument Mountain Motel
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
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

10/10 Excellent
"The owners and staff are very helpful. The rooms are comfortable and clean."
Mark 4-night trip
Posted 6 days ago
Travelodge by Wyndham Great Barrington Berkshires

Frequently asked questions

What are some accommodations with pools in Great Barrington?
Quality Inn Great Barrington: Offers a sauna, an outdoor pool, and spa services. Prospect Berkshires: Provides full, an indoor pool, and complimentary wired internet access. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Features buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Offers kitchens, a pool, and televisions. The Little Lion: Provides free self parking, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Great Barrington?
Make a point to visit attractions like Housatonic River Walk and Mahaiwe Performing Arts Center. During your stay, check out sights such as Housatonic River, Lake Mansfield Park, and Ski Butternut. Travelers love Great Barrington for its array of dining options.
When is the best time to book a hotel with a pool in Great Barrington?
Taking into account the local weather in Great Barrington 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 Great Barrington are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia