Family-friendly holiday rentals in Egremont

4.99 out of 5 average rating, 343 reviews

Loft in Great Barrington

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Apartment in Copake Falls

4.91 out of 5 average rating, 347 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

4.98 out of 5 average rating, 123 reviews

Loft in Great Barrington

Studio in Bucolic Berkshire Setting

The 600 Sq. Ft Studio with skylights has a sitting area with sofa-bed, flat screen TV/DVD, sleep area with queen-size bed, dining area, fully equipped kitchen and full bath with shower. Views overlook a 30 acre farm (south) and mountains (east). The studio is in a separate building with a private entrance. The 4 acre property includes perennial and vegetable gardens, an orchard and walking paths. The studio is easily accessible to biking, hiking, swimming, and numerous cultural attractions.

4.96 out of 5 average rating, 121 reviews

“On the Hill” Berkshires Colonial Retreat , 7ppl

Welcome to our serene Great Barrington retreat, only 5 min walk to Lake Mansfield. This 4-bedroom, 2.5-bathroom home features two lounge areas, nestled in a tranquil hillside setting. Fireplace, sunroom off the eat-in kitchen, and sliding glass doors opening onto two decks. Alfresco & formal dining options. 2 master bedrooms—one with an en-suite, others sharing a bath. Secluded with lush landscaping. 10 minutes to Catamount, 25 to Tanglewood and Jacob’s Pillow—pure Berkshires charm.

4.99 out of 5 average rating, 109 reviews

Bungalow in Egremont

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

4.99 out of 5 average rating, 114 reviews

Home in Sheffield

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

4.99 out of 5 average rating, 222 reviews

Apartment in Hillsdale

Serene Suite by Gt. Barrington, Hudson, Tanglewood

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

4.97 out of 5 average rating, 352 reviews

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

4.91 out of 5 average rating, 129 reviews

Beautiful Period Home in the Berkshires

Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house combines the charm of the antique with all the modern conveniences including two screened-in porches. Conveniently located five minutes from Gt. Barrington, MA and 25 minutes from Stockbridge, Tanglewood, and Hudson, NY. The property also sits adjacent to the Appalachian Trail with plenty of local options for hiking and skiing.

4.94 out of 5 average rating, 286 reviews

Modern Farm House 5 minutes from Great Barrington

Completely renovated with absolute style, this shingled farmhouse boasts clean modern decor with the architectural charm of a country home. Spacious & sunny kitchen that connects to the large outdoor patio with fireplace. Cozy living room with large flat screen television for streaming Netflix & Amazon. First floor bedroom with bathroom & laundry. The second floor master suite has cathedral ceilings & a jet powered glass shower.

4.93 out of 5 average rating, 160 reviews

Apartment in Sheffield

Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.