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Ashley Falls Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Ashley Falls vacation 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
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$139 nightly
The price is $155
Aug 31 - Sep 1
Total with taxes and fees
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, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$465 nightly
The price is $519
Sep 22 - Sep 23
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

3. 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
Sep 9 - Sep 10
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$366 nightly
The price is $409
Aug 24 - Aug 25
Total with taxes and fees
Home in Great Barrington
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, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$213 nightly
The price is $241
Aug 31 - Sep 1
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A sandy beach with a lake and forest in the background.

6. 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, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$299 nightly
The price is $334
Sep 13 - Sep 14
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

7. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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.
$269 nightly
The price is $301
Sep 1 - Sep 2
Total with taxes and fees
Cozy Riverside Berkshires Retreat
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
$261 nightly
The price is $292
Sep 13 - Sep 14
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$198 nightly
The price is $224
Aug 30 - Aug 31
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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.
$285 nightly
The price is $318
Sep 1 - Sep 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
A hot tub with a string of lights above it, set against a dark night sky.

11. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$355 nightly
The price is $397
Aug 24 - Aug 25
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 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.
$499 nightly
The price is $557
Sep 1 - Sep 2
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

13. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.6 out of 10, Excellent, (7 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$181 nightly
The price is $203
Aug 24 - Aug 25
Total with taxes and fees
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.

14. 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, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$359 nightly
The price is $401
Sep 9 - Sep 10
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

15. 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.
$551 nightly
The price is $582
Sep 21 - Sep 22
Total with taxes and fees
Treetop Hideaway in Tyringham
A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

16. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.2 out of 10, Wonderful, (5 reviews)
$338 nightly
The price is $377
Sep 14 - Sep 15
Total with taxes and fees
stylish Berkshires Retreat
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
$605 nightly
The price is $677
Aug 24 - Aug 25
Total with taxes and fees
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

18. 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, (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.
$681 nightly
The price is $770
Sep 22 - Sep 23
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
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.

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, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
$1,188 nightly
The price is $1,327
Aug 24 - Aug 25
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A two-story house with a covered porch, a front door, and a driveway.

20. Family home by Polo fields with great yard & game rm. EV charger, pet friendly!

Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Pine Plains
10.0 out of 10, Exceptional, (7 reviews)
"It felt clean, comfortable, accomodating, and most important, safe. Our family had an amazing time here and we will definitely visit again. Thank you!"
United States
Jon W.
$718 nightly
The price is $812
Aug 26 - Aug 27
Total with taxes and fees
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Lovely setting. Comfortable and well equipped townhouse. We are not much for the pool or mini golf type “activities” but we like the location near biking, hiking, theater and dance venues. And the ability to have meals in instead of using restaurants every meal. Looks like a great place for family vacations."
barbara 2-night trip
Posted 10 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

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 $301 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 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 4 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 6 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.