New Ashford Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for New Ashford holiday rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,373 reviews)
"Everything was great Room staff kitchen and pool . It was a quiet and peaceful stay"
United States
William
The price is HK$942
HK$1,139 total
includes taxes & fees
31 May - 1 Jun
Vacation Village in the Berkshires
Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (32 reviews)
"Cozy spot - everything was just right, exactly as described. Host was thoughtful and communicative and arrival/departure were very smooth. Would definitely stay here again! "
United States
Amy G.
The price is HK$529
HK$1,119 total
includes taxes & fees
28 May - 29 May
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is HK$705
HK$1,558 total
includes taxes & fees
28 May - 29 May
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,523
HK$3,618 total
includes taxes & fees
1 Jun - 2 Jun
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (2 reviews)
"It was an excellent place to stay. Super comfy and quiet, falling asleep to the sound of the creek. Well equipped with everything you need. Good fast wifi. Excellent value for the money. Great place if you want to really get away from it all."
United States
Seva L.
The price is HK$1,058
HK$1,851 total
includes taxes & fees
7 Jun - 8 Jun
Brookside cottage near the mountains and outdoor recreation
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is HK$776
HK$1,209 total
includes taxes & fees
28 May - 29 May
Taborton Harvest Boulder Pines Cabin in the woods
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is HK$2,272
HK$5,382 total
includes taxes & fees
31 May - 1 Jun
5BR Berkshire Home Mins To The Mountain
Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,536
HK$4,337 total
includes taxes & fees
28 May - 29 May
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$1,018
HK$2,265 total
includes taxes & fees
28 May - 29 May
Downtown | Waterfront | Walk to Shops
1 bedroom, free WiFi, bed sheets

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is HK$825
HK$1,264 total
includes taxes & fees
28 May - 29 May
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Smart TV

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is HK$910
HK$1,598 total
includes taxes & fees
31 May - 1 Jun
Cozy Home in Pownal VT
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is HK$940
HK$2,220 total
includes taxes & fees
31 May - 1 Jun
2-Bdr Apt In Town, By the Water
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is HK$1,851
HK$3,206 total
includes taxes & fees
28 May - 29 May
The Greylock Cabin
Exterior

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 reviews)
"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."
United States
Amanda H.
The price is HK$940
HK$2,418 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (12 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is HK$940
HK$2,114 total
includes taxes & fees
31 May - 1 Jun
New Studio In Town, By the Water
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$831
HK$1,856 total
includes taxes & fees
1 Jun - 2 Jun
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (105 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 HK$910
HK$2,410 total
includes taxes & fees
31 May - 1 Jun
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$762
HK$851 total
includes taxes & fees
8 Jun - 9 Jun
Huttopia Berkshires
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"Everything great!"
United States
Andrew P.
The price is HK$3,134
HK$4,682 total
includes taxes & fees
31 May - 1 Jun
Bear Creek Cabin
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is HK$1,192
HK$3,037 total
includes taxes & fees
28 May - 29 May
Near Tanglewood: Historic Summer Retreat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Ashford Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great place, nice amenities and convenient location, highly recommended."
Arthur 2-night trip
Posted 1 hour ago
The Cornell Inn, Lenox & The 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
  • Use the map to find apartments and other holiday homes in the New Ashford neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Ashford while they last

Look no further and take a look at our great range of rental properties in New Ashford!

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?

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views: This holiday home rental outside of New Ashford offers an outdoor pool, a fireplace and a BBQ 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. It offers a balcony, a garden and a selection of games 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 Zema's Nursery, 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.