A river flanked by autumn-colored trees and residential areas.

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Check availability on Housatonic Hotels with a Pool

Tonight
Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Housatonic hotels with a pool

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 bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
₩215,028
₩307,626 total
includes taxes & fees
Nov 1 - Nov 2
The Red Lion Inn
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 hotel room with two beds, a desk, a television, and a dresser.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

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.
₩218,082
₩243,598 total
includes taxes & fees
Nov 1 - Nov 2
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 bathroom with a large mirror, a sink, and a shower.
A breakfast area with a counter, coffee machine, and a display of pastries.
A hotel room with two beds, a desk, a TV, and a window with curtains.

3. 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.
₩137,108
₩153,149 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A large house with a balcony and a grassy yard.
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.
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.
₩140,138
₩156,534 total
includes taxes & fees
Oct 28 - Oct 29
The Little Lion
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A two-story house with a brick entrance and a white facade.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

5. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
  • Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
₩518,461
₩627,190 total
includes taxes & fees
Nov 1 - Nov 2
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A building with a porch and multiple windows, surrounded by purple flowers.
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.

6. 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.
₩158,417
₩203,424 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Club Vacations Oak 'n Spruce Resort
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.

7. 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.
₩170,516
₩190,466 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A poolside area with lounge chairs and a pool.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
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.

8. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
₩507,026
₩611,839 total
includes taxes & fees
Nov 1 - Nov 2
Prospect Berkshires
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 modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

9. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩143,895
₩160,731 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A backyard with a swimming pool, surrounded by grass and trees.
A stone fountain surrounded by trees in a park setting.
A modern bathroom with a black marble shower, gold fixtures, and a tiled floor.
Front of property

10. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
₩495,189
₩580,779 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Stockbridge
View all properties

Choose what matters most at hotels with a pool in Housatonic

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Housatonic Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"So glad we stayed here! Our room was decorated like a 1940s Norman Rockwell painting, but had every modern comfort. We were in Stevens House, a half-block from the main inn - the shared living areas were like a home and our en-suite room was super nice. We had one dinner in the inn that was fancy, but we usually ate at other good restaurants & the patisserie within 1 block. Many fun shops, and a good laundromat also within 1 block."
Ruth 3-night trip
Posted 4 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Clean, big rooms!"
Mark 1-night trip
Posted 16 hours ago
Howard Johnson by Wyndham Lenox
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Breakfast was great"
Thomas 1-night trip
Posted 4 days ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some hotels with pools in Housatonic?
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 Housatonic?
Surround yourself with nature at Housatonic River. During your stay, check out sights such as Norman Rockwell Museum, Berkshire Botanical Garden, and Naumkeag Museum.
When is the best time to book a hotel with a pool in Housatonic?
Taking into account the local weather in Housatonic 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 27°F. The snowiest months in Housatonic are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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