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Ashley Falls Vacation Rentals

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Our top choices for Ashley Falls vacation rentals

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
$366 nightly
The price is $409
Jul 29 - Jul 30
Total with taxes and fees
Home in Great Barrington

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (12 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
$628 nightly
The price is $701
Jul 20 - Jul 21
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
$281 nightly
The price is $313
Aug 10 - Aug 11
Total with taxes and fees
Cozy Riverside Berkshires Retreat

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
$377 nightly
The price is $421
Jul 21 - Jul 22
Total with taxes and fees
stylish Berkshires Retreat

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
$571 nightly
The price is $638
Aug 6 - Aug 7
Total with taxes and fees
Beachwood Cottage

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$178 nightly
The price is $202
Jul 26 - Jul 27
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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.
$311 nightly
The price is $347
Jul 20 - Jul 21
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$390 nightly
The price is $436
Jul 28 - Jul 29
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Lakefront Summer Stunner in New England Just 2 Hours From NYC

Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon
10.0 out of 10, Exceptional, (94 reviews)
"Great location, quiet and beautiful. Loved the trails, picturesque drives between small towns and cozy accommodations. "
United States
Chad J.
$525 nightly
The price is $595
Jul 25 - Jul 26
Total with taxes and fees
Lakefront Summer Stunner in New England Just 2 Hours From NYC

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$363 nightly
The price is $405
Jul 22 - Jul 23
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$392 nightly
The price is $438
Jul 28 - Jul 29
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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, (6 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
$1,191 nightly
The price is $1,330
Jul 23 - Jul 24
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
$981 nightly
The price is $1,096
Jul 20 - Jul 21
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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.
$653 nightly
The price is $690
Jul 22 - Jul 23
Total with taxes and fees
Treetop Hideaway in Tyringham

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (1 review)
"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.
$802 nightly
The price is $906
Jul 27 - Jul 28
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area

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
$171 nightly
The price is $192
Jul 20 - Jul 21
Total with taxes and fees
The Brooks Motel: Exceptional Suite

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
$594 nightly
The price is $665
Aug 9 - Aug 10
Total with taxes and fees
Gorgeous Mountain Views Retreat: Family & Nature

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (49 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
$2,160 nightly
The price is $2,413
Aug 2 - Aug 3
Total with taxes and fees
Great Barrington, Cabin Sleeps 14, Walk To Town

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$180 nightly
The price is $202
Jul 20 - Jul 21
Total with taxes and fees
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.
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Top Ashley Falls Hotel Reviews

Find out more about Ashley Falls

Everything you need to know about Ashley Falls vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashley Falls vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashley Falls vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ashley Falls in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $313 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashley Falls rentals

At Expedia, we put the best Ashley Falls vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Ashley Falls?

Yes, we have vacation rentals close to the most popular attractions in Ashley Falls, or you can choose a secluded option if you want a relaxing place to stay.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Ashley Falls is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Ashley Falls?

With 5 Expedia vacation rentals, you're sure 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 vacation rentals like in Ashley Falls?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Ashley Falls. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.