Your Guide to a Winter Weekend Getaway

Massachusetts in the wintertime can truly be a delightful place to stay. Though the weather outside may indeed be frightful, the fire inside is oh so delightful. However, to those souls willing to brave the cold and venture out, we have put together a three day itinerary just for you, so you can enjoy all the best of what the area has to offer and make the most of your winter vacation. Read on for our exclusive guide to a weekend winter getaway in Lenox, Massachusetts.

Find your favorite room for your romantic getaway in the BerkshiresDAY 1:

  • Arrive at Hampton Terrace mid-afternoon, where Stan or Amanda will welcome you, give you a tour of the public spaces and personally show you how things work in your room.
  • Visit Nejaimes Wine Shop, for spirits and gourmet food, around the corner to stock up for the weekend. We have full-size guest refrigerators in each building and personal fridges in each king suite.
  • Bring one of your Nejaimes purchases to our 1930s BYOB bar, stocked with glasses, plates & openers. Enjoy a glass of wine before dinner.
  • On your first evening, enjoy dinner within walking distance. We recommend Nudel, Alta or Bistro Zinc (be sure to make a reservation).
  • Come back to the Inn and enjoy complimentary top-shelf cognac or liqueurs in front of the main Inn fireplace. 
the Inn bar

Co-owner Susan enjoying a cocktail at our bar made by Brian Van Flandern, former bartender at Per Se in NYC and Food Network’s “America’s Top Mixologist.” Brian was at Hampton Terrace celebrating his honeymoon with wife, Kelly, and has returned multiple times.

  • Retire to your luxurious room with a cozy fireplace and Jacuzzi tub.

DAY 2:

  • Wake up to the smell of fresh coffee brewing. Complimentary Keurig coffee is available around the clock and Inn coffee is available at 7:30. Enjoy the all-you-can-eat hot breakfast buffet from 8:30 to 10:00. On Saturday we often serve a French toast sampler or several flavors of pancakes and sausage.
Fruit, tea, and baked goods for breakfast at our Lenox, MA inn

History and Culture Day:

  • Walk across the street to tour Ventfort Hall, the Gilded Age summer home of the JP Morgan family and now the “Museum of the Gilded Age.” See a spectacular restoration and learn why Lenox is the “Inland Newport.”
  • Take the beautiful drive north (45 minutes) to Williamstown and tour the Clark Art Institute, including one of the world’s largest collections of Impressionism. Then head 5 minutes east to North Adams and marvel at the Massachusetts Museum of Contemporary Art – 250,000 square feet of restored industrial spaces and equally impressive and creative art. Buy a combination ticket with the Clark and save money.
two people looking at art in an exhibit

Taking it all in, courtesy of MASS MoCA Facebook Page

Or….Winter Wonderland Active Day:

  • Skiing: For an inexpensive ski option choose Bousquet, one of the country’s oldest ski resorts, located 10 minutes from the Inn. Lift tickets are $47 (or $25 midweek) and $35 for ski equipment rental. For a more comprehensive ski experience choose Jiminy Peak, Catamount or Butternut – all between 30 and 45 minutes away.
  • Cross country or snow-shoeing: Located a mile from us is the Arcadian Shop, which rents cross-country skis and snow shoes. Out their back door is Kennedy Park, which has 15 miles of trails for hiking or skiing.

A couple skiing on winter getaway in Massachusetts

  • Return to the Inn late in the afternoon to enjoy our BYOB bar and thaw out in front of the Main Inn, or Carriage House fireplace


  • Since you ate within walking distance on Friday night, why not try one of the great restaurants in a surrounding town: The Old Mill in S. Egremont, Chez Nous in Lee, and Cafe ADAM in Great Barrington. Or dress up and enjoy a destination meal at Wheatleigh or Blantyre.

DAY 3:

  • Once again, coffee. Sunday breakfast buffet is usually savory, featuring a creative egg dish, grilled ham and seasoned grits, polenta or potatoes.
  • After checking out of the Inn, visit the Norman Rockwell Museum in Stockbridge to see many of his original paintings which capture “authentic New England.” Rockwell features the people and architecture of Stockbridge, so before heading home, we recommend lunch at the Red Lion Inn on Stockbridge’s Main Street (immortalized in one of Rockwell’s iconic paintings).
Complimentary cognac and liquer at Hampton Terrace Inn


Winters here at Hampton Terrace Inn are truly beautiful with warm amenities and a cozy atmosphere. Enjoy a glass of cognac by a roaring fire, take in the comfort of a hot dinner, or relax and unwind in a Jacuzzi tub in one of our luxurious rooms. Though the summer may have bid adieu as winter takes up residence, Hampton Terrace Inn continues to provide the best hospitality and comfort in the area. Come and see what all the fuss is about and, if you need to get away this winter season, look no further than our humble doorstep. We look forward to hosting you during your next escape to the Berkshires!

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