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Ashley Falls Holiday Rentals

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Our top choices for Ashley Falls holiday rentals

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$778
includes taxes & fees
12 Oct - 13 Oct
Cheerful 3-bedroom cottage with woodstove

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.6 out of 10, Exceptional, (5 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 NZ$247
includes taxes & fees
11 Oct - 12 Oct
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

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$570
includes taxes & fees
1 Oct - 2 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

4. 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, (52 reviews)
"Quaint very nice loved the space very cozy the hot tub was a nice touch I did use that a few times helped my sore back LOL everything went as expected I would stay here again"
United States
paul
The price is NZ$418
includes taxes & fees
28 Sept - 29 Sept
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is NZ$590
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington

6. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 NZ$557
includes taxes & fees
29 Sept - 30 Sept
Riverside Retreat in the Berkshires

7. 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, (79 reviews)
"Excellent host!"
United States
Kenny
The price is NZ$670
includes taxes & fees
28 Sept - 29 Sept
Ideal location for summer and winter activities with plenty of outdoor space.

8. 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 NZ$355
includes taxes & fees
28 Sept - 29 Sept
Cozy Camper tucked into the woods

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 NZ$336
includes taxes & fees
28 Sept - 29 Sept
The Brooks Motel: Exceptional Suite

10. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"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!! "
United States
Samantha G.
The price is NZ$985
includes taxes & fees
28 Oct - 29 Oct
Treetop Hideaway in Tyringham

11. 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, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is NZ$391
includes taxes & fees
4 Oct - 5 Oct
Peaceful and cozy 1 bed 1 bath in quaint Winchester

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is NZ$1,225
includes taxes & fees
28 Sept - 29 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.

13. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$647
includes taxes & fees
28 Sept - 29 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is NZ$691
includes taxes & fees
29 Sept - 30 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

15. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (52 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
The price is NZ$961
includes taxes & fees
23 Oct - 24 Oct
Cozy Cottage-Sunset On The Lake

16. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is NZ$607
includes taxes & fees
11 Oct - 12 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.

17. 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 NZ$352
includes taxes & fees
28 Sept - 29 Sept
The Brooks Motel: Exceptional Suite

18. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is NZ$1,186
includes taxes & fees
28 Sept - 29 Sept
Chic Barn Style * Fireplace * Near Stissing House

19. 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, (8 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$2,101
includes taxes & fees
28 Oct - 29 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

20. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is NZ$1,479
includes taxes & fees
28 Sept - 29 Sept
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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

Find out more about Ashley Falls

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ashley Falls holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ashley Falls. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ashley Falls. Seeing all the best attractions is bound to make you fall in love with Ashley Falls. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ashley Falls short-term rentals, that won’t be hard to do.

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.