Ashley Falls Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Ashley Falls

Exterior
The Blue Elm - A Historic Berkshire Cottage

Cottage in Sheffield

10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is ￥19,003
￥21,226 total
includes taxes & fees
Dec 5 - Dec 6
The Ponds at Foxhollow
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is ￥31,626
￥46,491 total
includes taxes & fees
Dec 2 - Dec 3
Pet Friendly Riverfront Home in Great Barrington
Interior
Peace and quiet on the lake

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Fridge, microwave, oven, stovetop
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Apartment in Great Barrington

9.6 out of 10, Exceptional, (38)
"Great location, spacious and well equipped "
United Kingdom
Alison F.
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is ￥66,377
￥124,560 total
includes taxes & fees
Dec 8 - Dec 9
Spacious 5-bedroom house in charming Lee with WiFi
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥22,771
￥58,756 total
includes taxes & fees
Dec 2 - Dec 3
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Vacation Home in Cornwall

9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Apartment in Lee

9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior
Antique Farmhouse Totally Restored

Vacation Home in Sheffield

9.8 out of 10, Exceptional, (93)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Cabin in Sherwood Forest

9.6 out of 10, Exceptional, (231)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods "
United States
Roberta F.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Vacation Home in Egremont

9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Smart TV, fireplace
Little Longbow Lakefront Chalet

Chalet in Becket

9.6 out of 10, Exceptional, (20)
"Beautiful property, very clean.. excellent place!"
United States
jason g.
Little Longbow Lakefront Chalet
Property grounds
Remodeled Lakefront retreat!!! Don't forget to book for ski season!

Vacation Home in Copake

9.8 out of 10, Exceptional, (14)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
United States
Melissa D.
Remodeled Lakefront retreat!!! Don't forget to book for ski season!
Fridge, microwave, oven, stovetop
A Grand property in Historic Stockbridge

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (104)
"Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand."
United States
David H.
A Grand property in Historic Stockbridge
Terrace/patio
Quintessential 6-BR Berkshires Lodge

Vacation Home in Becket

9.8 out of 10, Exceptional, (17)
"Great weekend away. Thank you!"
United States
Karen P.
Quintessential 6-BR Berkshires Lodge
Outdoor dining
The Goshen Glass Chalet

Vacation Home in Goshen

9.6 out of 10, Exceptional, (41)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet
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

Prospect Berkshires

Prospect Berkshires

10/10 Excellent
"Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession. "
Kate 2-night trip
Posted 3 days ago
Prospect Berkshires

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:

  • View our selection of featured holiday rentals in Ashley Falls
  • Use the map to find apartments and other holiday homes in the Ashley Falls neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashley Falls while they last

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?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental near Ashley Falls is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.