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Ashley Falls Hotels with Swimming Pool

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Check availability on Ashley Falls Hotels with Swimming Pools

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Ashley Falls 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 modern hotel lobby with a seating area, a sofa, and a large window with curtains.
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.
RM793
RM886 total
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An outdoor patio with wicker furniture and a small table, surrounded by a garden and trees.
A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.
A bathroom with a toilet, sink, bathtub, and a glass-enclosed shower.
A grand hallway with a chandelier, a staircase, and a table with flowers.

2. Blackberry River Inn

Blackberry River Inn
Norfolk
  • Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
RM611
RM703 total
includes taxes & fees
30 Sept - 1 Oct
Blackberry River Inn
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.

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.
RM486
RM543 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A rectangular swimming pool with a metal ladder, surrounded by a black metal fence.
A modern hotel room with a bed, sofa, leather chair, and a small table.
A tented area with lush greenery and a dining setup.
A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

4. Interlaken Inn & Resort

Interlaken Inn & Resort
Lakeville
  • Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
RM813
RM935 total
includes taxes & fees
26 Oct - 27 Oct
Interlaken Inn & Resort
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 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.
RM1,344
RM1,622 total
includes taxes & fees
1 Oct - 2 Oct
The Old Inn On The Green
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.

6. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
RM730
RM817 total
includes taxes & fees
30 Sept - 1 Oct
Little Cat Lodge
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.

7. 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.
RM477
RM612 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Club Vacations Oak 'n Spruce Resort
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
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.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
RM726
RM1,013 total
includes taxes & fees
19 Oct - 20 Oct
The Red Lion Inn
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 cabin with a bed, a chair, and a table by a large window overlooking a lake.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

9. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
RM1,338
RM1,631 total
includes taxes & fees
30 Sept - 1 Oct
Prospect 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 bathroom with a toilet, a shower with glass doors, and a towel rack with towels.
A two-story building with a gabled roof and a chimney.

10. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
RM422
RM471 total
includes taxes & fees
20 Oct - 21 Oct
The Little Lion
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Choose what matters most at hotels with a pool in Ashley Falls

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Ashley Falls Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."
Anthony 2-night trip
Posted 17 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"Fresh towels and trash removal every day without asking which is rare today. Owner was very nice and helpful. Will definitely stay again."
Dordy 4-night trip
Posted 17 hours ago
Monument Mountain Motel
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 23 hours ago
The Red Lion Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Just stayed one night to break up our trip. Everything was so clean and staff was great!"
Mark 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

8/10 Good
"More than anything, everything was clean. Everything was in working order, and the host was pleasant and seen tidying up around the property. There were many accommodations right around me. I had the best fish and chips ever at the big Y across the street."
Ray 1-night trip
Posted 3 weeks ago
Americas Best Value Inn Torrington CT

Frequently asked questions

What are some hotels with pools in Ashley Falls?
Quality Inn Great Barrington: Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Holiday Inn Club Vacations Oak 'n Spruce Resort: Offers a sauna, an outdoor pool and spa services. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Features a sauna, a seasonal outdoor pool and daily. Prospect Berkshires: Provides a full-service spa, a seasonal outdoor pool and 3 outdoor tennis courts.
What is there to see and do in Ashley Falls?
The picturesque setting of Housatonic River showcases the area's natural beauty. Discover sights such as Ashley Falls Woods and Bartholomew's Cobble during your stay.

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