Orlofseignir í Sheffield

Bull Hill Bungalow

Relax with the whole family at this peaceful, cozy home. Set on five acres located in the lovely Berkshires. Walk, bike, and hike the trails, ski Butternut and Catamount, rent a pontoon boat at nearby Twin Lakes, and explore the many great restaurants in Great Barrington and Salisbury. Immerse yourself in the culture. Tanglewood, Jacobs Pillow and many theaters are nearby. When in season, you can pick fresh vegetables from the garden, fruit from the fruit trees, and berries from the bushes.

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Perfect Peaceful Berkshire Location !

We have two rentals. Only one rental is rented at a time. This rental has 2 bedrooms, a fully equipped kitchen and is super clean. (THE 1 BEDROOM LISTING is called “Great Berkshire Getaway”) Conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit

The Kellogg House in the Heart of The Berkshires

The Kellogg House is conveniently nested in the heart of the Berkshires. Located within a short car ride from Sheffield, Great Barrington, and South Egremont, the area offers a superb food scene, local shopping, and cultural experiences. Cross Kellogg Rd, and you will find yourself on the 2,200 mile long Appalachian Trail. From lakes to mountains, you can access all that the Berkshire has to offer within minutes. The house is ideal for singles, couples, and families with children.

Family friendly house with fenced yard & fire pit

Hillside Haus is a modern house close to Catamount Mountain & Ski Butternut and Hotchkiss School. Enjoy high ceilings, a cozy fire pit, fenced yard, family-friendly amenities (including crib and high-chair), and fully stocked kitchen. Sleeps 6 comfortably, and includes an office space. Perfect for year-round getaways—ski in winter, hike and picnic at nearby lakes and campgrounds in summer. Quick drive to charming and vibrant Great Barrington for shopping, art, and restaurants.

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.

Berkshire Getaway~ No Pet Fee! Walk to Distillery

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within steps of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to great hiking, skiing, antiquing & more Seasonal Hot Tub is not available until further notice, sorry for the inconvenience.

The Blue Elm - A Historic Country Cottage

Welcome to The Blue Elm! A cozy and historic getaway located in Ashley Falls, MA. Set on 3.5 tranquil acres, the cottage ties into an early 19th century barn and is nestled amongst old growth maple trees. Enjoy this peaceful and convenient Berkshire location - only 15 minute drive to Catamount Ski Area, 17 minutes drive to Ski Butternut, Great Barrington and points north, and 5 minutes drive to Canaan, CT and points south.

Cottage on Scenic Road

NOTE!: As of Sept 2026 the wood stove is temporarily out of service and requires replacement. Please do not plan to be able to use the wood stove; I'll remove this note when the replacement is complete. One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.

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.

The Hideaway: Berkshire Home - village of Egremont

**NEW KITCHEN APRIL 2025!!**. Welcome to our family's home in the village of Egremont (part of Great Barrington). Both the house and property are open and inviting! You'll feel relaxed the minute you arrive. The kitchen is equipped with everything you should need for your stay. Our house is perfect for just a couple or a group. Please reach out to me with any questions!