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

Hotels with Swimming Pool in Great Barrington, Massachusetts

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Check availability on Great Barrington Hotels with Swimming Pool

Tonight
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Our top choices for Great Barrington hotels with a pool

An indoor swimming pool with clear water, surrounded by chairs and tables, large windows, and a tiled floor.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A Holiday Inn Express & Suites building with a stone facade, a covered entrance, and a parking lot.
A buffet with labeled containers for omelets and other dishes.

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.
P7,591
P8,479 total
includes taxes & fees
Sep 23 - Sep 24
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

2. 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.
P12,012
P13,418 total
includes taxes & fees
Aug 30 - Aug 31
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.

3. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
P6,943
P7,755 total
includes taxes & fees
Sep 1 - Sep 2
The Little Lion
A poolside area with lounge chairs and a pool.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

4. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
P20,273
P24,712 total
includes taxes & fees
Sep 17 - Sep 18
Prospect Berkshires
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 a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

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.
P19,675
P23,742 total
includes taxes & fees
Sep 1 - Sep 2
The Old Inn On The Green
A backyard with a swimming pool, a fenced area, and a view of the surrounding forest and hills.
A spacious living area with a brick fireplace, a dining table with chairs, and a view of the outdoors.
A spacious living area with a wooden ceiling, a brick fireplace, and a kitchen in the background.
A backyard with a hot tub, outdoor seating, and a patio area.

6. Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay
Great Barrington
P22,328
P55,797 total
includes taxes & fees
Sep 8 - Sep 9
Charming 6 Bdrm Countryside Stay
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

7. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P9,751
P10,891 total
includes taxes & fees
Sep 14 - Sep 15
The Yankee Inn
A large indoor swimming pool with clear water, surrounded by walls with informational posters and a reception area with a 'Welcome' sign.
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 hotel with balconies, a pond with rocks, and a clear sky.
A living room with a sofa, armchair, coffee table, and a patterned rug.

8. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
P7,220
P9,272 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Club Vacations Oak 'n Spruce Resort
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A wooden fire pit surrounded by six Adirondack chairs in 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.

9. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
P11,608
P13,001 total
includes taxes & fees
Aug 24 - Aug 25
Little Cat Lodge
A backyard with a swimming pool, lounge chairs, and a hot tub.
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.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P9,721
P13,924 total
includes taxes & fees
Sep 8 - Sep 9
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great location + well maintained property inside + outside"
Gerianne 5-night trip
Posted 3 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"A nice little hotel. Friendly staff. Well-maintained. And the nice thing is the location - it's in downtown Great Barrington, so you can walk to restaurants and other attractions without having to get into your car. No more than 30 minutes from Tanglewood, Shakespeare and Co., and Jacob's Pillow. Also a 20-minute walk from a small lake and beach."
Michael 11-night trip
Posted 5 hours ago
Quality Inn Great Barrington
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 5 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 1 day ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted 1 day ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"This is a comfortable, clean hotel with a charming proprietor. Reasonably priced too. I highly recommend!"
Maya 1-night trip
Posted 2 days ago
Monument Mountain Motel
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

8/10 Good
"We did not use the amenities. We were only there to sleep and for one night, but the staff was friendly and the room was cleanly enough."
Connie 1-night trip
Posted 7 days ago
Travelodge by Wyndham Great Barrington Berkshires

Frequently asked questions

What are some accommodations with pools in Great Barrington?
Quality Inn Great Barrington: Provides buffet, an indoor pool, and complimentary wired internet access. The Little Lion: Features a sauna, an outdoor pool, and spa services. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Offers full, an indoor pool, and complimentary wired internet access. Prospect Berkshires: Features a seasonal outdoor pool, an indoor pool, and buffet. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Offers 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.

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