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New Ashford Holiday Rentals

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Holiday Rentals in New Ashford

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2114)
"Great place!"
United States
Nicole
The price is NZ$197
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (984)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is NZ$288
includes taxes & fees
31 Oct - 1 Nov
Jiminy Peak Mountain Resort
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The Ponds at Foxhollow
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is NZ$317
includes taxes & fees
5 Nov - 6 Nov
Taborton Harvest Boulder Pines Cabin in the woods
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
United States
Stephanie R.
The Kemble- Built by a US Secretary of State in Lenox
Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is NZ$1,929
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak
Bear Creek Cabin
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,036
includes taxes & fees
5 Nov - 6 Nov
Bear Creek Cabin
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (32)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"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 NZ$555
includes taxes & fees
31 Oct - 1 Nov
Charming 3-bedroom Cabin for nature lovers
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is NZ$837
includes taxes & fees
31 Oct - 1 Nov
Comfortable Berkshires retreat on mtn resort, SISO
Taborton Harvest Timber Trails Unique cabin experience
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is NZ$318
includes taxes & fees
31 Oct - 1 Nov
Taborton Harvest Timber Trails Unique cabin experience
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
9.4 out of 10, Exceptional, (84)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
United States
Elizabeth R.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.8 out of 10, Exceptional, (46)
"Home is lovely, fun bedroom themes."
United States
Kate H.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
9.8 out of 10, Exceptional, (70)
"Beautiful location, very spacious, comfortable and clean."
United States
Aubrey G.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Cozy cabin in tranquil Canaan NY with WiFi, AC
Cozy cabin in tranquil Canaan NY with WiFi, AC
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
2.0 star property
10.0 out of 10, Exceptional, (12)
"Very comfortable and clean! The owner was responsive and helpful. The home was stocked with all the essentials. The location was convenient and quiet. Beautiful area to wander in and from. We are considering coming back in the fall for leaves changing. Loved it and would come back again!"
United States
Kim N.
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Contemporary Berkshire Home with Views of Taconic Golf Course
10.0 out of 10, Exceptional, (10)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
United States
MARK S.
Contemporary Berkshire Home with Views of Taconic Golf Course
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

Find out more about New Ashford

Everything you need to know about New Ashford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the New Ashford holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 New Ashford holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

New Ashford holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Ashford. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A New Ashford holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of New Ashford holiday rentals we have selected for you start as low as NZ$197 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on New Ashford rentals

At Expedia, we put the best New Ashford holiday 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 New Ashford 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 New Ashford holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Ashford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in New Ashford?

Yes, there are holiday rentals close to the most popular sights in New Ashford, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that New Ashford has to offer?

Amore Estate - beautiful room with many places to explore and relax in.: This holiday home rental outside of New Ashford offers an outdoor pool, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 wider area, you’ll find Green River Wildlife Management Area and Brodie Mountain.

What’s a holiday rental in New Ashford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in New Ashford. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family getaway.