Holiday Rentals in Ashley Falls

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Holiday Rentals in Ashley Falls

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is €153
includes taxes & fees
27 Feb - 28 Feb
The Ponds at Foxhollow

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (209)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (23)
"Property was clean. Check in was easy. Good location. Pet friendly. Good communication"
The price is €367
includes taxes & fees
8 Mar - 9 Mar
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (43)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (44)
"There is a game room that provided lots of fun. The linens were luxurious, the kitchen had every utensil. The yard is fenced in, the hot tub was great, we loved it!"
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.6 out of 10, Exceptional, (7)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.8 out of 10, Exceptional, (27)
"We are two families that travel together every year for a long weekend. This getaway did not disappoint. It was a beautiful home with amazing views! We enjoyed watching the 6 inches of snow falling from the hot tub! The house was big enough for all of us. Four adults and 3 teenagers. The teenagers had a great time playing video games and we all enjoyed the shuffleboard table! We could watch different movies on different floors! We made dinners and there was plenty of room for all of us around...
The Meadows House @ Otis Ridge w/ 7-person hot tub

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

10.0 out of 10, Exceptional, (139)
"We had a wonderful trip, the kitchen is fully stocked with tons of kitchen tools, 2 slow cookers, etc! Cooking basics were available, soaps, dishwasher pods etc! The rooms were great! The playroom was amazing for all the kids! We had a wonderful time and will be back! "
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

Lakeside Retreat Just You, The Lake & The View!

9.8 out of 10, Exceptional, (69)
"We had a lovely stay. Views are amazing. Property owner was very responsive and helpful. Would love to go back in the fall."
Lakeside Retreat Just You, The Lake & The View!

Sanctuary of the Sacred Dream-Entire Property. Close to CATAMOUNT

Sanctuary of the Sacred Dream-Entire Property. Close to CATAMOUNT

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is €846
includes taxes & fees
10 Mar - 11 Mar
Guesthouse Cabin vacation rentals in Berkshire County

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (14)
"The cabin was cozy and accommodating. We had a great family trip. There is a perfect little hill in the front that the children used for sledding. Many great memories were made."
Romantic and Secluded Berkshire's Gem
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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Other types of properties in Ashley Falls you may be interested in

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (600)
"Great stay again. My family has been going here 3 years in a row, and its always a great experience "
The price is €140
includes taxes & fees
2 Mar - 3 Mar
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Love the history and ambiance. Service excellent. Restaurant dinner just fair. Clean rooms. Guests should not have to pay for music in the bar. Parking good. Very quiet. "
The price is €201
includes taxes & fees
12 Mar - 13 Mar
The Red Lion Inn

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (999)
"Two adults and a baby to enjoy winter wonderland: it worked very well! Very close to everything! "
The price is €107
includes taxes & fees
5 Mar - 6 Mar
The Black Swan Lee - Lenox, Ascend Hotel Collection
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.

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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.