Ashley Falls Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

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

10.0 out of 10, Exceptional, (35 reviews)
"Julie was an excellent host. She responded quickly to my questions and provided us with a long list of local restaurants and activities.The house is lovely! It was very clean and had everything that we would need for our stay. We appreciated the big kitchen and the open living room- dining room space. "
United States
Kathleen E.
The price is NZ$1,212
includes taxes & fees
24 Mar - 25 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is NZ$1,476
includes taxes & fees
24 Mar - 25 Mar
Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (4 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 NZ$2,181
includes taxes & fees
24 Mar - 25 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is NZ$1,172
includes taxes & fees
24 Mar - 25 Mar
Guesthouse Cabin vacation rentals in Berkshire County
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is NZ$1,089
includes taxes & fees
24 Mar - 25 Mar
CT Gate House Goshen CT, Gate House Goshen CT
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is NZ$1,144
includes taxes & fees
30 Mar - 31 Mar
Spacious 5-bedroom house in charming Lee with WiFi
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is NZ$2,446
includes taxes & fees
31 Mar - 1 Apr
A Country Lodge Straight Out of the Pages of a Great Novel
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is NZ$661
includes taxes & fees
24 Mar - 25 Mar
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is NZ$526
includes taxes & fees
24 Mar - 25 Mar
Dugway Hideaway Walking Distance to Lime Rock Park
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$847
includes taxes & fees
29 Mar - 30 Mar
Cheerful 3-bedroom cottage with woodstove

Holiday Home in Great Barrington

Cozy Riverside Berkshires Retreat
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$530
includes taxes & fees
24 Mar - 25 Mar
Cozy Riverside Berkshires Retreat

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is NZ$505
includes taxes & fees
30 Mar - 31 Mar
Home in Great Barrington

Holiday Home in Monterey

Treetop Hideaway in Tyringham
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is NZ$939
includes taxes & fees
24 Mar - 25 Mar
Treetop Hideaway in Tyringham
The price is NZ$1,828
includes taxes & fees
1 Apr - 2 Apr
Secluded escape w/ hot tub + pizza oven+ fireplace
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is NZ$1,010
includes taxes & fees
24 Mar - 25 Mar
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
9.6 out of 10, Exceptional, (5 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is NZ$768
includes taxes & fees
24 Mar - 25 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Holiday Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1 review)
"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 NZ$988
includes taxes & fees
6 Apr - 7 Apr
Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$636
includes taxes & fees
1 Apr - 2 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is NZ$326
includes taxes & fees
24 Mar - 25 Mar
The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5 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 NZ$342
includes taxes & fees
24 Mar - 25 Mar
The Brooks Motel: Exceptional Suite
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashley Falls Hotel Reviews

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 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 NZ$505 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?

Peace and quiet on the lake: This holiday home rental outside of Ashley Falls is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Ashley Falls?

With 4 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.