Photo by The Curious Zephyr

New Ashford holiday homes

We found 270 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in New Ashford to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – New Ashford

Showing deals for:11 Dec - 18 Dec

Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
Workstation with a view!
View of the lower deck from the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,339
for 7 nights, 1 home
NZ$1,191 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Walk to Spring Street and brand new Williams Bookstore
Beautiful period woodwork and Victorian details
Build a cozy fire in our wood fireplace, watch the game or play pool!
Gourmet kitchen has everything you need to prepare delicious meals
Exceptional
(155 reviews)

Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!

Williamstown

7% off
NZ$10,186
for 7 nights, 1 home
NZ$1,455 per night
includes taxes & fees
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Dining
Terrace/patio
Private kitchen
Room
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
NZ$5,044
for 7 nights, 1 cottage
NZ$721 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Room
Interior
Exterior
Interior
Exceptional
(41 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
NZ$2,886
for 7 nights, 1 home
NZ$412 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Interior
Outdoor dining
Dining
Renovated kitchen
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
NZ$6,636
for 7 nights, 1 home
NZ$948 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Large Smart HDTV with electric fireplace in living room, showing dining room
View from 2nd floor balcony (after leaves have fallen)
Views from the back of the 16 acres on the property
Entrance into house with wood burning stove to right and staircase
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$3,990
for 7 nights, 1 home
NZ$570 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Interior
Spring at Jiminy Peak 2019
Night skiing view from living room
Country Inn heated pool & outdoor hot tub is open all year.  Towels are provided
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
NZ$9,565
for 7 nights, 1 home
NZ$1,366 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Private kitchen
Private kitchen
Room
Interior
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$4,032
for 7 nights, 1 home
NZ$576 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Heidi visiting Jane's 18th Century Studio
Interior
Interior
Backside of barn
Exceptional
(99 reviews)

19th c. Barn in the Berkshires

Cheshire

8% off
NZ$4,920
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
19th c. Barn in the Berkshires
another view of kitchen
new backyard table
kitchen and laundry room area
another view of same bedroom as well as makeup table
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,182
for 7 nights, 1 apartment
NZ$883 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Interior
Living area
King size bed in 2nd story primary bedroom
Living area
Very good
(5 reviews)

Walk to campus; open concept kitchen/living;nature trail at end of this quiet st

Williamstown

14% off
NZ$3,505
for 7 nights, 1 home
NZ$501 per night
includes taxes & fees
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Property grounds
Interior
Interior
Room
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
NZ$4,732
for 7 nights, 1 home
NZ$676 per night
includes taxes & fees
Historic Stone Church in The Berkshires
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The charming city of New Ashford awaits you

Enjoy the festivals and other features of New Ashford. This romantic and scenic city entices travellers with its skiing and mountain views. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around New Ashford

Are you hoping to discover attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that New Ashford has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Waubeeka Golf Links (3.6 mi / 5.8 km)
  • Jiminy Peak Mountain Resort (4.3 mi / 7 km)
  • Bousquet Ski Area (13.3 mi / 21.4 km)
  • Kennedy Park (15.7 mi / 25.2 km)
  • Berkshire East Ski Resort (18.6 mi / 30 km)
  • Zema's Nursery (9.1 mi / 14.7 km)

Exploring the natural landscape of New Ashford

Whether you're an active traveller or just want to spend some time taking in the scenery, New Ashford is a great place to get out in nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Brodie Mountain (2.1 mi / 3.4 km)
  • Mount Greylock State Reservation Visitor Center (3.8 mi / 6.1 km)
  • Mount Greylock State Reservation (3.9 mi / 6.2 km)
  • Mount Greylock (4.3 mi / 7 km)
  • Pontoosuc Lake (7.5 mi / 12.1 km)
  • Windsor Lake Park (9.1 mi / 14.6 km)

How to get to and around New Ashford

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 12.7 mi (20.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Albany, NY (ALB-Albany Intl.), which is 30.5 mi (49.2 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in New Ashford?
According to our data, houses are the most in-demand type of holiday home in New Ashford. But as you'd expect, everyone's idea of an epic trip will differ. Bookabach has holiday homes of all shapes and sizes, so you're sure to find your perfect match.
How much does it cost to rent a holiday home in New Ashford?
Season, length of stay and property type are among the factors that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From cosy cabins to expansive luxury villas, all Bookabach holiday homes offer unbeatable value.
How much does it cost to rent a beach house in New Ashford?
The average price for a holiday home by the beach in New Ashford depends on when you're travelling and the type and size of property you want. Find prices quickly and easily on Bookabach by entering your preferred travel dates and destination. Then use the filter tool to pick the number of bedrooms and amenities that you need, like air conditioning, a pool and WiFi.
What are popular home amenities in New Ashford?
A fireplace, a nearby river and a garden head the list of most popular home amenities in New Ashford. Whether you're heading away as a party of one, with your spouse or as a family, Bookabach can help you find a holiday home that matches your style with all the conveniences you're looking for.
What are the top attractions for families in New Ashford?
Keep the kids amused at these fun family-friendly attractions in New Ashford:
  • Williamstown Historical Museum
  • Hopkins Observatory
  • Massachusetts Museum of Contemporary Art
How old do you have to be to rent a holiday home in New Ashford?
The minimum required age is normally 16, 18 or 21. It can change between properties on Bookabach, so check the rules of your preferred New Ashford holiday home before booking your trip.
How long can I rent a holiday home in New Ashford for?
How long you can rent a holiday home in New Ashford depends on the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With a range of creature comforts such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get someplace just right to call your home away from home in New Ashford.