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New Ashford Holiday Rentals

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Holiday Rentals in New Ashford

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2006)
"All around loved everything about the place! "
The price is NZ$181
includes taxes & fees
21 Sept - 22 Sept
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (974)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is NZ$298
includes taxes & fees
16 Sept - 17 Sept
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is NZ$184
includes taxes & fees
16 Sept - 17 Sept
Huttopia Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (129)
"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"
The Ponds at Foxhollow
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is NZ$309
includes taxes & fees
16 Sept - 17 Sept
Taborton Harvest Boulder Pines Cabin in the woods
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is NZ$797
includes taxes & fees
16 Sept - 17 Sept
Comfortable Berkshires retreat on mtn resort, SISO
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

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."
The Kemble- Built by a US Secretary of State in Lenox
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is NZ$1,866
includes taxes & fees
17 Sept - 18 Sept
Hancock Village Inn at Jiminy Peak
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (39)
"We enjoyed our stay!!"
The price is NZ$989
includes taxes & fees
16 Sept - 17 Sept
Bear Creek Cabin
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (147)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (64)
"Great value, so much better than all the touristy motels in the area!"
The price is NZ$349
includes taxes & fees
16 Sept - 17 Sept
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

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."
The price is NZ$308
includes taxes & fees
16 Sept - 17 Sept
Taborton Harvest Timber Trails Unique cabin experience
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (19)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (82)
"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! "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is NZ$553
includes taxes & fees
30 Sept - 1 Oct
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Fireplace, books

3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest

9.6 out of 10, Exceptional, (37)
"My friends and I had the most beautiful rainy weekend here to celebrate my 40th birthday. The spot was perfect for the 5 of us and the river was such a wonderful bonus to our peaceful trip!"
3BR Riverfront Log Home with Steam Sauna, Soaring Glass Wall & Private Forest
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (7)
"We had a wonderful four night stay at this home in Williamstown. Kathy, the owner, was great and easy to reach. The home was thoughtfully and thoroughly appointed, comfortably accommodating our extended family of ten. The grounds were beautifully maintained and the views of the Berkshires were breathtaking. We wouldn’t hesitate to stay again and we would highly recommend this lovely property. "
Contemporary Berkshire Home with Views of Taconic Golf Course
Charming Apt in 18th c Berkshire Farmhouse
1 bedroom, WiFi, bed sheets

Charming Apt in 18th c Berkshire Farmhouse

9.4 out of 10, Exceptional, (36)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
The price is NZ$349
includes taxes & fees
16 Sept - 17 Sept
Charming Apt in 18th c Berkshire Farmhouse
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Interior

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

9.6 out of 10, Exceptional, (71)
"We love this comfortable cottage and quiet location, perfect for a relaxing vacation spent bird watching, biking the nearby rail trail, and hiking with our dog. This was our fourth time staying here-- impressed with the beautiful updates to the master bedroom, now a suite with its own bathroom! We'll be coming back again!"
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Lovely clean hotel with great breakfast. "
Linda 1-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about New Ashford

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$181 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This holiday home rental outside of New Ashford is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 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’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.