Sheffield, MA, USA apartments for rent

Enjoy total privacy at this cozy mountain home on 40 acres, just minutes from ski resorts and charming shops. With floor-to-ceiling windows showcasing stunning views and radiant heating for warmth, this pet-free retreat is perfect for families seekin...

Welcome to The Blue Elm - a cozy and historic Berkshire 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 conv...

I JUST purchased my dream house! I have been searching for a lake house in the Berkshires for years & when this came on the market I just had to say YES! It is a cozy newly renovated home situated on a 2 acre private peninsula surrounded on 3 sides b...

Beautiful, comfortable artist's house, that is tastefully furnished. Located on a very quiet 5 acre property abutting Mt Everett State Reservation with Race Brook runs past the house. A 2.5hour drive from New York City and Boston. You can just relax,...

Bring friends or the whole family to this cozy accessible Berkshire County Country getaway. Only 5 minutes to Great Barrington! Close to Butternut and Catamount ski areas, Twin Lakes for boating, fishing, skiing, boarding etc., state parks, Tanglewoo...

Game Room | 2,734 Sq Ft | ~6 Mi to Campbell Falls State ParkWhether you’re chasing waterfalls in the summer, leaf-peeping in the fall, or skiing in the winter, this all-season home is ideal for enjoying the beauty of the Berkshires. Situated on a...

2,262 Sq Ft | Ping-Pong Table | Nestled on Mill Pond | Take a break from the city and book this Sheffield vacation rental in the Berkshires! The 3-bed, 2-bath house boasts a retro interior, a full kitchen, an enclosed porch, and stellar pond and fall...

Historic fully updated brick house originally built in 1812 in the Berkshires in Western Massachusetts on one of the prettiest roads in the area. Minutes from Great Barrington and close to borders of Connecticut and New York, the spacious house sits ...

Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mountain views, it comfortably accommodates up to 12 guests. Beyond the 6th guest, there's a $135 per person fee. Couples enjoy speci...

Beautiful country home with 3 bedrooms plus a kids loft, 6 minutes to Great Barrington with lots to discover. 12 minutes to Butternut Skiing, 15 minutes to Catamount Skiing. Electric car charger, hot tub, fire place, game room with pool table and pac...

Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. The rarest o...

Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete privacy, yet 10 minutes to downtown Great Barrington. Close to skiing at both Catamount and Butternut. There is room for everyone, w...

Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. Recently updated, the farmhouse seamlessly blends rich history with modern comforts, offering an exceptional retreat. Just 7 minute...

Our home is a beautiful mountain-style home (exposed beams, wood floors, all new appliances) on a quiet rural road with commanding views of the Housatonic valley and Mt. Everett. Six miles to Great Barrington in the heart of the Berkshires. The house...

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 literal steps of Sunset Me...

One of the very few waterfront homes available for rent. What other houses offer you 150 feet private lakefront where you can awake to birdsong? absolute best house in the best little town for the full Berkshire experience. If you want your own total...

Our secluded property is a great place to relax and enjoy the company of your friends and family. The house has all the amenities: well-equipped kitchen, fireplace, sauna, Foosball and Ping-Pong tables, patio and an outdoor fire pit. Sheffield is a p...

Fresh, cozy & serene, the Little House is set back from the road with several acres of woods behind & a wildlife preserve just across the road. Sheffield is the oldest town in the Berkshires, home to beautiful houses from the 1700's that overlook gor...

Family or couples getaway! 3 bedrooms plus library, Sleeps6-8 Abeautiful 3050 Sq. Ft., 2-Story Colonial and attached 2 car garage. Large, upscale chefs kitchen where everything is first class. Marble counters. Professional Blue Star (6 burner) gas ra...

This rambling farmhouse has a balanced mix of meticulous restoration with an eccentric flair. Undermountain Farm is a home carefully designed with warmth and spirit. It also has a unique collection of fascinating antiques and collectibles.Enjoy c...

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-...

Settle in among the beauty of the Berkshires at Whitney, a private retreat overflowing with comfort and charm. Enjoy the fresh mountain air and the surrounding foliage from a screened patio, complete with a foosball table and seating. Whitney feature...