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Ashley Falls Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Ashley Falls holiday rentals

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (46 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,391
HK$3,211 total
includes taxes & fees
10 Nov - 11 Nov
Cheerful 3-bedroom cottage with woodstove
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$600
HK$837 total
includes taxes & fees
11 Nov - 12 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A living room with a grey sofa, a fireplace, a television, and a cabinet with glass doors.

3. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.4 out of 10, Exceptional, (55 reviews)
"It was a nice stay…worked well for the event we attended in town. The host was very nice to work with"
United States
Roberta S.
The price is HK$833
HK$1,602 total
includes taxes & fees
5 Nov - 6 Nov
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

4. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
Sharon Retreat w/ Private Yard
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

5. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,389
HK$1,679 total
includes taxes & fees
5 Nov - 6 Nov
The Brooks Motel: Exceptional Suite
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

6. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is HK$1,695
HK$2,533 total
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A sandy beach with a lake and forest in the background.

7. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is HK$1,640
HK$2,551 total
includes taxes & fees
9 Nov - 10 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A wooden cabin interior with a bench, a rug, and a hanging plant.

8. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is HK$812
HK$1,432 total
includes taxes & fees
8 Nov - 9 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A wooden cabin with a porch, a grill, and a flower planter.

9. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (80 reviews)
"We very much enjoyed our two week stay in July. The cabin suited our needs in every regard. Our lab was also able to fully relax, whether it was napping on the screen porch or sitting by the fire pit. For those looking to explore the region, the location could not be better situated. Hoping to return over Christmas."
United States
Richard M.
The price is HK$1,373
HK$2,698 total
includes taxes & fees
8 Nov - 9 Nov
Ideal location for summer and winter activities with plenty of outdoor space.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

10. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is HK$1,381
HK$2,393 total
includes taxes & fees
19 Nov - 20 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A recreational vehicle (RV) with a kitchenette area, a dining table with chairs, and a patio umbrella.

11. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is HK$1,130
HK$1,367 total
includes taxes & fees
5 Nov - 6 Nov
Cozy Camper tucked into the woods
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

12. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
A dining area with a wooden table, chairs, and a ceiling fan.

13. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is HK$1,589
HK$2,362 total
includes taxes & fees
8 Nov - 9 Nov
Leaf-Peeper Paradise in the Berkshires
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

14. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,389
HK$1,679 total
includes taxes & fees
5 Nov - 6 Nov
The Brooks Motel: Exceptional Suite
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

15. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is HK$416
HK$2,174 total
includes taxes & fees
9 Nov - 10 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

16. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,144
HK$2,803 total
includes taxes & fees
5 Nov - 6 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

17. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$2,704
HK$4,520 total
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A hot tub with a string of lights above it, set against a dark night sky.

18. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,257
HK$2,938 total
includes taxes & fees
5 Nov - 6 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

19. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$3,139
HK$5,233 total
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashley Falls Hotel Reviews

the Alander

the Alander

10/10 Excellent
"Room was fresh and super clean. Comfortable bed and the sheets and towels were soft and high quality. Staff was also super helpful getting us settled in. Cozy bar and dining room. However my rigatoni pasta bowl was puzzling. Raw uncooked plum canned tomatoes, raw zucchini cubes, and a handful of only slightly blanched broccoli raab sitting on top of it all! The freshly baked bread and home made butter service was wonderful though."
Bette 1-night trip
Posted 3 hours ago
the Alander

Find out more about Ashley Falls

Search for holiday rentals in Ashley Falls on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashley Falls using one of the methods below:

  • View our selection of featured holiday rentals in Ashley Falls
  • Use the map to find apartments and other holiday homes in the Ashley Falls neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashley Falls while they last

Look no further and take a look at our great range of rental properties in Ashley Falls!

Frequently asked questions

Are there holiday rentals in Ashley Falls?

Yes, there are holiday rentals close to the most popular sights in Ashley Falls, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ashley Falls has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Ashley Falls is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Ashley Falls?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Ashley Falls stay.

What can I see and do in Ashley Falls?

While exploring the area, visit family-friendly sights like Harney and Sons Tea Tasting Room, or get outside and enjoy nature at Housatonic River. Other places in town to visit include Ashley Falls Woods and Bartholomew's Cobble.

What are holiday rentals like in Ashley Falls?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashley Falls. Holiday rentals feature amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family gatherings.