Ashley Falls Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Ashley Falls vacation rentals

Exterior detail

Vacation Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
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 ￥16,792
￥101,691 total
includes taxes & fees
Jan 22 - Jan 23
CT Gate House Goshen CT, Gate House Goshen CT
Interior

Vacation Home in Sherwood Forest

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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.
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ￥25,331
￥60,970 total
includes taxes & fees
Jan 21 - Jan 22
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ￥23,054
￥39,529 total
includes taxes & fees
Jan 26 - Jan 27
Home in Great Barrington
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

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 ￥25,141
￥31,700 total
includes taxes & fees
Jan 20 - Jan 21
The Brooks Motel: Exceptional Suite
Exterior

Vacation Home in Goshen

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
2.0 star property
The price is ￥37,854
￥80,493 total
includes taxes & fees
Jan 21 - Jan 22
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Smart TV, books

Vacation Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is ￥28,462
￥72,767 total
includes taxes & fees
Jan 20 - Jan 21
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Interior

Vacation Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ￥21,346
￥42,389 total
includes taxes & fees
Feb 1 - Feb 2
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9 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 ￥62,141
￥109,681 total
includes taxes & fees
Jan 20 - Jan 21
Guesthouse Cabin vacation rentals in Berkshire County
Interior

Vacation Home in Goshen

Whispering Estate Guest House - A Romantic Countryside Getaway
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is ￥85,385
￥138,751 total
includes taxes & fees
Jan 20 - Jan 21
Whispering Estate Guest House - A Romantic Countryside Getaway
Interior

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥32,019
￥47,069 total
includes taxes & fees
Jan 20 - Jan 21
Family Ski Getaway in the Berkshires
TV, fireplace, printers

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3 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 ￥89,512
￥210,020 total
includes taxes & fees
Jan 20 - Jan 21
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

Vacation Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is ￥47,278
￥102,792 total
includes taxes & fees
Jan 20 - Jan 21
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV, DVD player, books, stereo

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (26 reviews)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ￥49,017
￥87,780 total
includes taxes & fees
Jan 25 - Jan 26
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Vacation Home in Lee

Spacious 5-bedroom house in charming Lee with WiFi
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 ￥75,107
￥136,175 total
includes taxes & fees
Feb 12 - Feb 13
Spacious 5-bedroom house in charming Lee with WiFi
3 bedrooms, iron/ironing board, WiFi, bed sheets

Vacation 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.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
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 ￥25,141
￥31,700 total
includes taxes & fees
Jan 20 - Jan 21
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"fine inn"
Mark 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Ashley Falls

Search for holiday rentals in Ashley Falls on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashley Falls using one of the methods below:

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Look no further and take a look at our great range of rental properties in Ashley Falls!

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?

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

How many vacation rentals will I find in Ashley Falls?

With 3 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.