Ashley Falls Holiday Rentals from €151: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Sheffield

Kelly R.

includes taxes & fees

2 Nov - 3 Nov

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

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

Great Barrington

Deborah S.

includes taxes & fees

30 Oct - 31 Oct

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

Great Barrington

Marc R.

includes taxes & fees

12 Oct - 13 Oct

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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

winsted

traci

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Great Barrington

Janet G.

includes taxes & fees

13 Oct - 14 Oct

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

6. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

12 Oct - 13 Oct

A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Winchester

Thomas C.

includes taxes & fees

1 Nov - 2 Nov

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

8. Cozy Cottage-Sunset On The Lake

Otis

Michael S.

includes taxes & fees

23 Oct - 24 Oct

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.

Hillsdale

Kenny

includes taxes & fees

12 Oct - 13 Oct

A staircase with a wooden handrail and a white wall with a light switch.

10. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

26 Oct - 27 Oct

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Housatonic

Peter S.

includes taxes & fees

13 Oct - 14 Oct

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

12. Cozy Camper tucked into the woods

Sandisfield

"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...

hannah w.

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.

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

Sherwood Forest

Sharon K.

includes taxes & fees

14 Oct - 15 Oct

14. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Great Barrington

Mark M.

includes taxes & fees

19 Oct - 20 Oct

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

A two-story house with a front porch, surrounded by lush greenery and trees.

17. Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

Annetta D.

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

Sherwood Forest

Frank M.

includes taxes & fees

12 Oct - 13 Oct

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

19. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

9 Nov - 10 Nov

A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

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

Cornwall

Candice S.

includes taxes & fees

10 Nov - 11 Nov

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

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

Sign in

Sign up, it's free

Top Ashley Falls Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

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, apart-hotels, 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 favorite 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 depends 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 €151 per night. Entering your travel dates in the search wizard you might find 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashley Falls holiday rentals

1. Cheerful 3-bedroom cottage with woodstove

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

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