Luxury Hotels & Resorts in New Ashford from AU$109

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on New Ashford Luxury Hotels

Our top choices for New Ashford luxury hotels

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (292 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AU$232
includes taxes & fees
27 Feb - 28 Feb
Lakehouse Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (573 reviews)
"Very pleasant and relaxing place to stay"
United States
steve
The price is AU$308
includes taxes & fees
11 Mar - 12 Mar
The Williams Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (281 reviews)
"This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again."
United States
Nancy
The Four Chimneys Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is AU$346
includes taxes & fees
18 Feb - 19 Feb
Hampton Terrace Inn

South Shire

South Shire
4.0 star property
Bennington
9.0 out of 10, Wonderful, (122 reviews)
"A+ service, room we stayed in was perfect size with king bed. had an issue with heater first night but Inn Keeper was great to deal with and provided alternative heat source on first evening plus they have working fireplace (bonus++). We stayed 3 nights and just enjoyed ourselves during our visit. would definitely stay here again."
Canada
TROY
The price is AU$283
includes taxes & fees
25 Feb - 26 Feb
South Shire

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AU$635
includes taxes & fees
25 Feb - 26 Feb
33 Main

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AU$172
includes taxes & fees
1 Mar - 2 Mar
The Central Downtown Inn & Suites
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Top New Ashford Hotel Reviews

Frequently asked questions

Are you searching for the perfect hotel for your luxury holiday in New Ashford?
Use Expedia and let us help you arrange a flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Albany, NY (ALB-Albany Intl.) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to get what you need to make your stay relaxing and comfortable. If you want an upscale hotel with fine dining, a spa or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that New Ashford has to offer. New Ashford has some interesting things to see and do including Mount Greylock State Reservation and Green River Wildlife Management Area, so you might want to take in the local sights during your visit.
When can I expect good weather in New Ashford?
Planning for the weather is an important factor for making your trip to New Ashford a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in New Ashford are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
What's there to see and do in New Ashford?
Experience New Ashford with a stop at Mount Greylock State Reservation, Brodie Mountain and Williamstown Theatre Festival. If you have some spare time during your trip, you might want to check out Waubeeka Golf Links and Mount Greylock State Reservation Visitor Center.

Explore a world of travel with Expedia