Ashley Falls Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for Ashley Falls hotels

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

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

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

Great Barrington

Bruce

฿4,821

฿5,385 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A framed painting of a white horse on a wooden dresser, a white fireplace with a black mantle, and two green vases with white flowers on the wall.

2. The White Hart

Salisbury

William

฿15,117

฿17,384 total

includes taxes & fees

7 Oct - 8 Oct

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

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

A cozy living room with floral wallpaper, a sofa, a coffee table, and two lamps.

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

3. Blackberry River Inn

Norfolk

Rachel

฿5,034

฿5,789 total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

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

Great Barrington

Maria Dulce

฿3,188

฿3,561 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 Quality Inn sign, a brick building, and a parking lot with cars.

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

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

5. Quality Inn Great Barrington

Great Barrington

Joan

฿2,523

฿2,818 total

includes taxes & fees

1 Nov - 2 Nov

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

A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

6. Wilder House Berkshires

Sheffield

Lynn

฿6,926

฿7,736 total

includes taxes & fees

29 Oct - 30 Oct

A hammock chair on a porch with a white railing and a grassy yard in the background.

A covered porch with white railings and rocking chairs.

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

A two-story building with a flat roof, solar panels, and a small patio area.

7. Locust Tree Bed and Breakfast LLC

East Canaan

Daniel

฿3,524

฿4,052 total

includes taxes & fees

5 Oct - 6 Oct

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

A tented area with lush greenery and a dining setup.

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

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

8. Interlaken Inn & Resort

Lakeville

Stacie

฿6,685

฿7,688 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

9. Gedney Farm

Great Barrington

Terri

฿6,769

฿7,425 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 motel with a parking lot and several cars parked.

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.

10. Monument Mountain Motel

Great Barrington

Victor

฿2,009

฿2,243 total

includes taxes & fees

1 Nov - 2 Nov

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.

11. The Old Inn On The Green

Great Barrington

Catherine

฿9,732

฿11,744 total

includes taxes & fees

1 Nov - 2 Nov

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

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 bar area with a green counter, two pendant lights, and shelves stocked with bottles.

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

12. the Alander

Copake

Thomas

฿4,849

฿5,431 total

includes taxes & fees

6 Oct - 7 Oct

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

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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

13. The Red Lion Inn

Stockbridge

Stephan

฿5,286

฿7,572 total

includes taxes & fees

3 Nov - 4 Nov

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

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.

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.

14. Manor House Inn

Norfolk

Kevin

฿11,712

฿13,000 total

includes taxes & fees

5 Oct - 6 Oct

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

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.

15. Quality Inn Lee - Lenox South

Lee

Christine

฿3,680

฿4,110 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A house with a stone patio and wooden stools.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

16. Little Cat Lodge

Copake Falls

Kees

฿5,104

฿5,717 total

includes taxes & fees

2 Nov - 3 Nov

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

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

17. East Rock Inn

Great Barrington

ERIK

฿4,484

฿5,009 total

includes taxes & fees

4 Nov - 5 Nov

A large house with a balcony and a grassy yard.

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

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 two-story building with a gabled roof and a chimney.

18. The Little Lion

Great Barrington

Lidia

฿3,473

฿3,880 total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

A living room with a patterned carpet, two sofas, a dining table, and chairs.

A motel with a two-story structure, multiple rooms with red doors, and a central staircase.

19. Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

Mark

฿2,651

฿2,961 total

includes taxes & fees

18 Oct - 19 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 dining area with large windows, wooden furniture, and a view of a lake.

A lakeside dock with kayaks and a covered boat ramp.

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

Lee

Bob

฿3,879

฿4,333 total

includes taxes & fees

1 Nov - 2 Nov

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Ashley Falls Woods

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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

฿2,523

฿2,818 total

1 Nov - 2 Nov

includes taxes & fees