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

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

1. 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)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AU$167
includes taxes & fees
5 Dec - 6 Dec
Cozy 1-bedroom studio in serene Great Barrington with AC
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

2. 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 AU$576
includes taxes & fees
19 Nov - 20 Nov
Cheerful 3-bedroom cottage with woodstove
A sandy beach with a lake and forest in the background.

3. 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 AU$407
includes taxes & fees
8 Nov - 9 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.

4. 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 AU$271
includes taxes & fees
16 Nov - 17 Nov
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

5. 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 AU$316
includes taxes & fees
6 Dec - 7 Dec
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$454
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A wooden fence, a potted plant, a wooden bench, and a small garden area with a stone pathway.

7. 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 AU$251
includes taxes & fees
8 Nov - 9 Nov
Cozy Camper tucked into the woods
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

8. 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 AU$388
includes taxes & fees
9 Nov - 10 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

9. 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 AU$299
includes taxes & fees
16 Nov - 17 Nov
The Brooks Motel: Exceptional Suite
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

10. 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 AU$473
includes taxes & fees
15 Nov - 16 Nov
Ideal location for summer and winter activities with plenty of outdoor space.
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

11. 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.
The price is AU$665
includes taxes & fees
9 Nov - 10 Nov
Sharon Retreat w/ Private Yard
A dining area with a wooden table, chairs, and a ceiling fan.

12. 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 AU$430
includes taxes & fees
13 Nov - 14 Nov
Leaf-Peeper Paradise in the Berkshires
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

13. 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 AU$940
includes taxes & fees
15 Nov - 16 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

14. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is AU$905
includes taxes & fees
21 Nov - 22 Nov
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

15. 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 AU$415
includes taxes & fees
8 Nov - 9 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

16. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$1,738
includes taxes & fees
8 Nov - 9 Nov
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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 AU$829
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

18. 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 AU$307
includes taxes & fees
8 Nov - 9 Nov
The Brooks Motel: Exceptional Suite
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.

19. 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)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is AU$501
includes taxes & fees
8 Nov - 9 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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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Find out more about Ashley Falls

Everything you need to know about Ashley Falls holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashley Falls holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashley Falls holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Ashley Falls holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashley Falls. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashley Falls holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashley Falls holiday rentals we have selected for you start as low as AU$166 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ashley Falls rentals

At Expedia, we put the best Ashley Falls holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashley Falls rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashley Falls holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashley Falls. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.