House holiday rentals in Sheffield

Stylish colonial, 4 acres, 9 min Gt Barrington

Enjoy a beautiful, modern-furnished colonial house situated on 4 private acres, built in 1800 & updated for maximum comfort. Easy driving to Tanglewood, Jacob's Pillow, Ski Butternut, Kripalu and many fantastic dining options. Open kitchen/living room with cathedral ceilings, 4 bedrooms with views of spacious property and surrounding farmland. Full kitchen, dishwasher, woodburning stove, 2 bathrooms, laundry, wifi. Minimally and stylishly furnished, with space for couples, families & friends.

Family · Location · TV

Best of the Berkshires + Hot Tub by Evergreen Home

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

Family · Location · Cleanliness

Under Mountain House

Our home is designed to be your home away from home! It has been newly renovated with comfort in mind so you can enjoy your stay in the Berkshires. Whether you are here to hike parts of the Appalachian Trail, stroll into town for a leisurely meal, enjoy Lime Rock Race Track or explore the many surrounding New England towns you can be assured you will always have a comfortable home to come back to!! My home is located just a 3 minute walk to the center of town and the historic White Hart.

Family · Location · Kitchen

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

Location · Value · Hospitality

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Location · Value · Getting around

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.

Location · Family · Check-in

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Value · Family · Hospitality

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Location · Family · Parking

Bright/Spacious Getaway at foot of the Berkshires

Centrally located in the Hudson Valley at the foot of the Berkshire mountains, this is a beautiful duplex. After raising our family in the larger side, we moved to the attached, yet fully separate apartment . We're looking to rent the larger 2,900 sq. ft., 4 bedroom/3 bathroom side, which sits on 1.5 acres with a fenced in backyard and parking area. 60" satellite Tv in big room and two other smaller tvs in master bedrooms.

Value · Location · Getting around

The House in a Beautiful Small Upstate Town

This is a house to enjoy with the family with a lot of space and many activities, in a small town but with a lot of tourism. You can visit the town which it has a small cinema, and Rail trail for walking or biking, and it has many restaurants nearby. This house includes a living room, kitchen, 4 bedrooms, 3 full bathrooms, deck, and a big backyard. You can also do BBQ s outside.

Value · Family · View

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!

Location · Family · Kitchen

Prime location for the best of the Berkshires

Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.

Location · Value · Hiking