Ashley Falls Holiday Rentals, Massachusetts: Private House Rentals

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

Go beyond your typical stay in Ashley Falls

Pet friendly

Apartment

Pool

Condo

Spa

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Ashley Falls hotels

A cozy living room with a fireplace, leather armchairs, a coffee table with fruit, and a bookshelf.

A grand hallway with a chandelier, a staircase, and a table with flowers.

A room with a fireplace, two striped armchairs, and a floral drape.

A dining area with multiple tables set for service, wooden floors, and large windows offering a view of the outdoors.

1. Blackberry River Inn

Norfolk

Rachel

Rp2.682.300

Rp3.084.645 total

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a large bed, a chair, and a window with curtains.

A dining area with yellow chairs and tables, a kitchen in the background, and a clock on the wall.

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

A covered porch with a dining area, a sofa, and decorative wall art.

2. The White Hart

Salisbury

William

Rp8.054.947

Rp9.263.234 total

includes taxes & fees

7 Oct - 8 Oct

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

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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.

3. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Bruce

Rp2.568.749

Rp2.869.292 total

includes taxes & fees

2 Nov - 3 Nov

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

4. Quality Inn Great Barrington

Great Barrington

Joan

Rp1.344.369

Rp1.501.660 total

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a large bed, a dresser, a chair, and a mirror.

A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.

5. Wilder House Berkshires

Sheffield

Mark

Rp3.690.666

Rp4.122.337 total

includes taxes & fees

29 Oct - 30 Oct

A sign for 'The Logust Tree Bed & Breakfast' with a contact number.

A covered porch with white railings and rocking chairs.

A dining room with a wooden table, chairs, a vase with flowers, and red curtains.

A bedroom with a wooden bed, two bedside tables, a window with curtains, and a radiator.

6. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

Rp1.877.610

Rp2.159.252 total

includes taxes & fees

5 Oct - 6 Oct

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

Rp1.698.790

Rp1.897.548 total

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with a swing chair and a bench overlooking a lake.

A lakeside deck with Adirondack chairs, a canoe, and a wooden railing.

A modern bar area with a counter, bar stools, and a variety of bottles.

A modern hotel room with a bed, sofa, leather chair, and a small table.

8. Interlaken Inn & Resort

Lakeville

Stacie

Rp3.562.094

Rp4.096.409 total

includes taxes & fees

26 Oct - 27 Oct

A dining area with round tables set for two, a fireplace, and a mural on the wall.

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.

A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

9. The Old Inn On The Green

Great Barrington

Catherine

Rp5.185.780

Rp6.257.627 total

includes taxes & fees

1 Nov - 2 Nov

A rustic wooden building labeled 'GEDNEY FARM' with a signboard indicating 'SERVING DINNER WED-FRI 5:00-9:00pm'.

A spacious living room with a fireplace, patterned armchairs, and a staircase leading to an upper level.

An outdoor patio with wooden tables and chairs, surrounded by greenery.

A wooden sign with "GEDNEY FARM" written on it, surrounded by lush greenery and purple flowers.

10. Gedney Farm

Great Barrington

Terri

Rp3.606.620

Rp3.956.462 total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

A motel with a parking lot and several cars parked.

11. Monument Mountain Motel

Great Barrington

Victor

Rp1.070.238

Rp1.195.412 total

includes taxes & fees

1 Nov - 2 Nov

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

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.

A wooden wall with a white pendant light fixture.

12. Prospect Berkshires

Egremont

Conor

Rp5.552.361

Rp6.801.240 total

includes taxes & fees

2 Nov - 3 Nov

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

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 covered porch with wicker furniture and hanging flower baskets.

13. The Red Lion Inn

Stockbridge

Stephan

Rp2.816.772

Rp4.034.711 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

14. Quality Inn Lee - Lenox South

Lee

Christine

Rp1.960.761

Rp2.190.170 total

includes taxes & fees

25 Oct - 26 Oct

A modern building with a dark exterior, outdoor seating area with wooden chairs, and string lights.

A dog standing at a door entrance with a wooden floor and a mat with paw prints.

A modern living room with a sofa, armchair, and coffee table. There is a bed with a headboard and pillows, a lamp, and a shelf with items.

A dining table set with plates of food, wine glasses, and bottles, with a chandelier above and shelves above holding glasses and bottles.

15. the Alander

Copake

Thomas

Rp2.583.949

Rp2.894.023 total

includes taxes & fees

6 Oct - 7 Oct

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 room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

16. The Little Lion

Great Barrington

Lidia

Rp1.850.787

Rp2.067.329 total

includes taxes & fees

18 Oct - 19 Oct

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

17. East Rock Inn

Great Barrington

ERIK

Rp2.389.447

Rp2.669.013 total

includes taxes & fees

4 Nov - 5 Nov

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

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 poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.

18. Little Cat Lodge

Copake Falls

Kees

Rp2.719.852

Rp3.046.234 total

includes taxes & fees

2 Nov - 3 Nov

A patio with a round metal table, a glass of white wine, and a red umbrella.

A cozy room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A large, two-story house with a steeply pitched roof, stone foundation, and a well-maintained garden with various shrubs and a fountain.

A dining table with a plate of food and two wine glasses, set in a room with leather furniture and a fireplace in the background.

19. Manor House Inn

Norfolk

Kevin

Rp6.240.818

Rp6.927.308 total

includes taxes & fees

5 Oct - 6 Oct

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A dining area with large windows, wooden furniture, and a view of a lake.

20. The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Bob

Rp2.067.159

Rp2.309.017 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Ashley Falls attractions

Ashley Falls Woods

You can take time to visit Ashley Falls Woods during your travels to Ashley Falls.

See properties

Top Ashley Falls Hotel Reviews

Blackberry River Inn

10/10 Excellent

"Lucas was them best innkeeper and made us feel at home. Breakfast was amazing."

Quality Inn Lee - Lenox South

10/10 Excellent

"Room was clean, bed was comfortable, breakfast was good, centrally located for our days events!"

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Steven was very helpful and so nice. He went above and beyond to help me find a lost item."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

The Millerton Inn

10/10 Excellent

"charming cozy stay, staff was awesome!"

Troutbeck

10/10 Excellent

"Absolutely stunning escape. Just go"

Little Cat Lodge

10/10 Excellent

"Quiet, clean and very good place to relax"

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."

More cheap stays in Ashley Falls

Quality Inn Great Barrington

372 Main Street Great Barrington MA

Rp1.344.369

Rp1.501.660 total

1 Nov - 2 Nov

includes taxes & fees