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New Ashford Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for New Ashford holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,575 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
The price is S$137
includes taxes & fees
31 Aug - 1 Sept
Vacation Village in the Berkshires
A wooden cabin with a covered deck, a fire pit, and string lights.

2. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is S$138
includes taxes & fees
8 Sept - 9 Sept
Huttopia Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,100 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is S$163
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

4. 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 S$704
includes taxes & fees
29 Aug - 30 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A red house with a porch, surrounded by a grassy yard and trees.

5. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is S$492
includes taxes & fees
1 Sept - 2 Sept
Two Brooks Lodge
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
Corinne 1-night trip
Posted 8 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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’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.