New Ashford Vacation Rentals

Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for New Ashford vacation rentals

Exterior

Cabin in Sand Lake

Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (14 reviews)
"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"
United States
Abby L.
The price is ￥19,770
￥28,967 total
includes taxes & fees
Mar 12 - Mar 13
Taborton Harvest Boulder Pines Cabin in the woods
TV

Vacation Home in Florida

Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ￥29,062
￥53,948 total
includes taxes & fees
Mar 12 - Mar 13
Florida Mountain Log Cabin
Dining

Vacation Home in Charlemont

Charlemont Chalet - A 15 Acre Private Retreat
The price is ￥53,870
￥103,542 total
includes taxes & fees
Mar 16 - Mar 17
Charlemont Chalet - A 15 Acre Private Retreat
Fridge, microwave, oven, stovetop

Vacation Home in Hoosick Falls

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
9.8 out of 10, Exceptional, (103 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is ￥18,328
￥48,028 total
includes taxes & fees
Mar 22 - Mar 23
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is ￥47,358
￥74,589 total
includes taxes & fees
Mar 15 - Mar 16
Bear Creek Cabin
Exterior

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ￥26,619
￥29,733 total
includes taxes & fees
Mar 15 - Mar 16
Huttopia Berkshires
Exterior detail

Vacation Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is ￥30,604
￥50,262 total
includes taxes & fees
Mar 23 - Mar 24
3-bedroom house in beautiful Berkshires, close to amenities!
Exterior

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay "
United States
Lydia T.
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Outdoor dining

Apartment in Williamstown

Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is ￥20,561
￥45,723 total
includes taxes & fees
Mar 12 - Mar 13
Downtown | Waterfront | Walk to Shops
Outdoor dining

Apartment in Williamstown

2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (12 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is ￥18,979
￥44,826 total
includes taxes & fees
Mar 13 - Mar 14
2-Bdr Apt In Town, By the Water
Exterior

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,295 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is ￥16,413
￥20,065 total
includes taxes & fees
Mar 15 - Mar 16
Vacation Village in the Berkshires
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥39,856
￥84,623 total
includes taxes & fees
Apr 1 - Apr 2
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Outdoor dining

Vacation Home in Pittsfield

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ￥42,480
￥78,133 total
includes taxes & fees
Mar 12 - Mar 13
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is ￥18,347
￥38,867 total
includes taxes & fees
Mar 16 - Mar 17
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior

Vacation Home in Williamstown

North Getaway Cottage
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is ￥32,027
￥70,930 total
includes taxes & fees
Mar 12 - Mar 13
North Getaway Cottage
Outdoor dining

Apartment in Hancock

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
9.8 out of 10, Exceptional, (7 reviews)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
The price is ￥18,347
￥38,867 total
includes taxes & fees
Mar 16 - Mar 17
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Gift shop

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is ￥17,398
￥37,983 total
includes taxes & fees
Mar 17 - Mar 18
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Indoor pool

Apartment in Hancock

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
9.8 out of 10, Exceptional, (22 reviews)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is ￥18,347
￥38,867 total
includes taxes & fees
Mar 16 - Mar 17
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Gift shop

Apartment in Hancock

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is ￥18,347
￥38,867 total
includes taxes & fees
Mar 16 - Mar 17
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Interior

Cabin in Stephentown

Charming 3-bedroom Cabin for nature lovers
6.8 out of 10, (3 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is ￥20,798
￥46,215 total
includes taxes & fees
Mar 12 - Mar 13
Charming 3-bedroom Cabin for nature lovers
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 New Ashford Hotel Reviews

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Clean, good service "
Heather 1-night trip
Posted 2 hours ago
Courtyard by Marriott Lenox Berkshires

Find out more about New Ashford

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

  • View our selection of featured holiday rentals in New Ashford
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Look no further and take a look at our great range of rental properties in New Ashford!

Frequently asked questions

Are there vacation rentals in New Ashford?

Yes, there are vacation rentals close to the most popular local attractions in New Ashford, or you can choose a more remote option if you'd like a relaxing place to stay. New Ashford is known for its ski areas and mountain views. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that New Ashford has to offer?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental outside of New Ashford offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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 selection of games and a hot tub.

What’s there to see and do in New Ashford?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Mount Greylock State Reservation. In the larger area, you’ll find Green River Wildlife Management Area and Brodie Mountain.

What’s a vacation rental in New Ashford like?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in New Ashford. Vacation rentals provide amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.