Great Barrington MA Real Estate & Homes for Rent

This classic picture-perfect contemporary home features an open floor plan, cathedral ceilings, updated everything, and an in-ground heated pool. In addition, this outstanding Alford property is located on 5.46 acres, and it is less than a 10 minute drive to the center of Great Barrington with all of that town's fabulous restaurants, shops and food stores. The screened porch overlooks a recently constructed stone patio and deck with a built-in top-of-the-line gas grill and an easy access to the fabulous in-ground heated pool. If you are looking to escape to the ideal vacation home, this listing should be Option #1. The famous real estate saying about location, location, location could have this property as its photography definition. Rental rates beyond the July and August period are significantly lower. Landlord fills propane tank prior to move-in, and tenant fills propane tank at time of move-out.

The perfect Berkshire country retreat for large gatherings awaits you. Bring your friends to enjoy this stunning home and property on 18+ acres perched atop the Berkshire hills with panoramic views. This generous and tasteful home offers endless spaces to relax and entertain. Lounge on the expansive deck with gorgeous views all around. Take a swim in your own pond overlooking the valley below. Enjoy lunch in the screened porch, or catch up on your reading in the sun room. Warm up near the fire place in the extraordinary great room. Prepare feasts of your choice in the enormous well stocked kitchen. And when it's time to retire for the evening, everyone will have a place to stay as this gracious home sleeps 12 comfortably. When you feel like venturing beyond this wonderfully private oasis, Great Barrington is just minutes away along with all of the best of the Berkshires. Available June and July 2024

Modern and Stylish in Sheffield - Open floor plan, stylish and modern family rental in convenient Sheffield. Lovely sunny lawn, trampoline, and detached garage. Quiet country roads, excellent for biking and walking, convenient to Route 7 and Route 41. Cement floors, high ceilings, big bright windows, renovated bathrooms. The primary bedroom has southern exposure and an en suite bath with a walk-in shower with Kohler fixtures, a 16-inch rain head, and custom tile work. A separate family wing, with vaulted ceilings and polished concrete radiant floors, includes 2 bedrooms, an extensive family room, guest bathroom with thermostatic Kohler fixtures. Six-foot soaking tub with custom concrete surround.

Just completed, charming, lig two-bedroom carriage house. Set on the grounds of a quietly elegant house in bucolic New Marlborough. Relax and enjoy the myriad attractions of the Berkshire hills, quiet walks, fantastic hiking, biking, skiing, charming towns and villages replete with a multitude of restaurants and farmers markets and of course, renown cultural attractions. 15 minutes to Great Barrington.You'll find a cozy living room and delightful kitchen with doors leading to the terrace, a primary suite with a private bath, a guest bedroom and second bathroom, and a second-floor aerie with a sitting room and study area; all beautifully appointed. Lofty and light. Both the living room and primary bedroom access the terrace and gardens offering gorgeous views of the pond and meadows beyond.Available beginning December 2023 by the month. $3,200. per month. July and August $7,000. July and August include weekly housekeeping. Available for the Christmas through

PRISTINE COUNTRY OASIS!Experience this wonderful Berkshire country setting nestled in the middle of hundreds of gloriously private, open acres in a bright, airy comfortable home! Recently renovated from top to bottom this 4 bedroom, 3 bath home offers plenty of room for guests in pristine surroundings and easy living. True privacy and convenience come together with this property located on the border of Stockbridge and Lee. Available fall 2024 and beyond.

Welcome to your story book Hudson Valley rental. The 1830's original home is brimming with functional updates and unique modern design. Stone lined gardens run along the property, highlighting amenities such as a swimming pond, sauna, outdoor shower, patio fire pit, tree-house, private trails, and a free standing artist/writers studio. The 4 bed, 3 bath home maintains its charm with original beams, hardwood floors, and stone masonry. Improvements throughout; renovated bathrooms, top of the line appliances, slate countertops, wine cellar, playroom with loft, and mudroom. Additions include a 900 sqft family room- floor to ceiling windows, sliding glass doors, radiant heat, hand made tiles, pizza oven and fireplace, and custom sound system. Trails from the home lead into the Rheinstrom Audubon nature preserve with 100's of acres of land for enjoyment. The Hamlet of Hillsdale is a 20 minute bike ride on the Rail Trail, also accessed from the property. Available May 25.

TYRINGHAM VALLEY ESTATE. Sitting high above the valley, a magical home where family and friends can unwind and enjoy the slower pace of summer. This gracious home offers large gathering spaces indoors and out. From the generous double living room to the delightful screened cottage and numerous spots in between, there is plenty of room to enjoy quiet moments and time together. Gracious gardens and the heated swimming pool offer mesmerizing views, south across the valley. Three well-appointed guest rooms are located on the first floor; one offering a private suite. A primary bedroom suite on the second floor. 10 minutes to Stockbridge, 18 minutes to the gates of Tanglewood, 15 minutes to Jacobs Pillow. Enjoy slow food, great restaurants, hiking, cycling, museums & more. Magic happens in the Berkshires. Available August 2024. Max Occupancy 8. Pets will be considered. Includes weekly housekeeping, trash removal, and all utilities.

Available Immediately! Second floor apartment. Three bedroom with a full bathroom and a half bathroom. In unit washer and dryer. The house is equipped with generator so you never have to worry about power outages again. Pets negotiable. First, last, security and 1 month broker fee. Employment verification, background check, credit check and references required.

Enjoy a unique retreat at the Lodge! This fully furnished rental boasts a large open floor plan that includes kitchen/dining area, seating area in front of large stone fireplace, sleigh bed, tv area and a beautiful custom bar. One full bath and one half bath. Plenty of space for a gathering or just a few. Vacation at the Lodge and enjoy the beauty of the Northwest Corner of Connecticut. Surrounded by hiking trails, nature preserve and nearby Twin Lakes. Close to the Berkshires and many ski areas. This rental is available by the month. Square footage and room size are approximate.

***Available 5/24/2024 through 9/8/2024 $35,000/term or $12,000/month, 3 months minimum*** Taconic Waterfront Carriage House. Step through the Living Room French doors to the terrace and gardens overlooking the Channel from Twin Lakes, or enjoy serene, landscaped rock vistas from any room in this turn-of-the-century Carriage House. Master Bedroom suite, plus two Bedrooms with Bath on the first floor; fourth Bedroom and Bath on the second floor. The elegant lofted-ceiling Living Room includes a fireplace, Steinway piano, built-in bookshelves, and a dining area. Also, enjoy the Gourmet kitchen; study or office; extensive walks and gardens; screened-in gazebo, and canoe for outdoor enjoyment. Paddle into the larger lake, or drive to nearby Lakeville Lake for supervised swimming. Minutes from Salisbury CT, Great Barrington MA, Millerton NY, and only 2hrs to NYC.

Charming Twin Lakes Lakefront Retreat Nestled along the serene shores of Washining Lake, this beautiful 4 bedroom, 3 bath home offers a tranquil retreat for those seeking relaxation and natural beauty. With its spacious interior and breathtaking views, this rental property promises an unforgettable experience. This lake home is the perfect place to create lasting memories. Whether you seek a peaceful retreat or an adventurous getaway, this lake home offers the best of both worlds. Soak in the breathtaking views and listen to the soothing sounds of nature on the brick landing overlooking the lake. This home offers a harmonious blend of tranquility and convenience. The surrounding area is renowned for its natural beauty with nearby amenities to ensure that all your daily needs are within easy reach. Please note that a one-time cleaning fee of $300 will be in addition to the monthly rent. No Pets and No Smoking. The property includes a shared brick landing with the owners, providing convenient access to the lake. However, the large dock is off-limits to renters. You can still enjoy the lake from the shared dock, which is a perfect spot for fishing, relaxing, or launching smaller watercraft. There is also an EV Charger available. *Unavailable for month of July & August 2024*

Welcome to the summer Lake House of your dreams! Available from Memorial Day to Labor Day, entire term $65K. July $25K, August $25K or 4 weeks for $25K. Overlooking the picturesque Washining Lake, affectionately known as the larger of the two Twin Lakes. This home boasts 4 bedrooms, 3.5 baths and a one-of-a-kind view. Entering the home, you will step into an open concept kitchen and dining area, attached to a cozy sunroom. On the other side of a large, stone fireplace, are large leather couches backed up against a jaw-dropping view of the lake. Down a short hallway off the kitchen is a laundry room, and small den area. Also on the main living area is a master suite with access to the large deck and a full master bath. Up the stunning, live edge staircase to the second floor are 3 more bedrooms, one of which is a second primary with ensuite bath. Outside, a wraparound deck provides the perfect place to soak up the summer and enjoy the breeze off the lake. A large yard surrounding the home dips down to the water with ample lake access. Enjoy your private dock with water toys. Take in the serenity of the lake from the new deck and new deck furniture. Looking for more summer fun? Rent a boat for a day on the lake at O'Hara's Landing Marina located less than 1 mile away. Enjoy a summer concert on the lawn at Tanglewood, go shopping in Great Barrington, grab a bite to eat at one of the many restaurants in Salisbury.

The Kemble Berkshires is a registered Great Estate built in the 1880s for a U.S. Secretary of State and New Jersey State Senator - now newly renovated by Shared Estates with bright minimalist finishes and world-class amenities. The property has manicured landscaping with massive rolling views of the Stockbridge Bowl. Whether you want to relax in the library room with its array of books from the early 1900s, jam out in the music room, snuggle up in front of one of the home's seven fireplaces or enjoy a drink with a friend at the private bar, you will find beautiful spaces to enjoy in groups or in solitude. 100% carbon neutral. Events up to 175.The property offers a dining room (including custom farmhouse dining table), a professional kitchen, herb and vegetable garden, fire pit and expansive multi-level stone patios and decks. Events up to 175 are permitted and a tent is provided for rain contingency (first weekend in May to third weekend in October)

MAGICAL Available from June 1 - October 31, 2024, this fabulous Cottage is absolutely enchanting! Large Living Room/Dining Room with stone wood-burning fireplace, Kitchen with propane-fired woodstove, large Primary Bedroom with Bath, Home Office overlooking the backyard, Hall Bath, second floor Bedroom, a Front Porch, an enormous vegetable Garden which you may pick from, and Blackberry River frontage to cool your toes. The wonderful Owner lives in the additional house on the property and directs her landscaping business out of her home. This is the happy place to live a fairytale summer and fall. June $3000. July $3000. August $3500. Sept $3000. October $3000. Utilities included.

Spend your summer in this amazingly elegant home perched in natures wonderland minutes from the center of picturesque Salisbury. No expense was spared in this carefully curated home of design enthusiasts dreams. This homes light and airy nature is welcoming and comfortable. The large floor to ceiling windows provide amazing light and give you the sense that you are residing in a tree house. Plenty of rooms for guests: three bedrooms with King beds (one of them can be converted to two twins), as well as a portable crib. The house features 3 full bathrooms, one on each floor. The chefs kitchen featuring a gas range will make entertaining a breeze. Host your guests at the large dining table, outside on the wrap around deck or on the expansive lawn. Roast marshmallows in the evenings at the firepit. The lower level provides an additional entertaining space that could be used as a playroom, media room or additional guest quarters (with a pull out bed). As a summer resident of Salisbury, you have access to Lakeville Lake including swimming, basketball, playground. Spend your days exploring nearby Great Barrington, Sharon, Salisbury, and Millerton. Head to Tanglewood on the weekends for unbelievable live performances or to nearby Sharon Playhouse for local theatre. All utilities included. Tenant is responsible only for liability insurance, lake pass & credit check. Available: 6/28-9/3 ($15k per 4 weeks)

Recently renovated bright and open 3 bedroom, 2 full bath home. New Appliances with washer and dryer with plenty of space for a home office, den or study. This rental home is within close proximity to Falls Village and North Canaan. Surrounding towns Salisbury, Cornwall and Sharon are within minutes along with the Massachusetts and New York boarders. NO PETS and NO SMOKING Rental Application must be approved by Management company prior to any viewings.

The Winthrop Estate is a registered Great Estate built in 1875 for Henri Braem, US Ambassador to Denmark and Partner in Cunard Steamship Lines, famous for the ultra-luxurious Queen Mary ship line among others. Braem sold the property to the Winthrop family, descendants of John Winthrop, the founding governor of Massachusetts, from which the property took its current name. The manor is now freshly renovated with modern touches thoughtful of its origins and includes world-class amenities.

Set amongst the bucolic Berkshire foothills surrounding Lake Copake, this newly built and beautifully appointed 6 bedroom, 5.5 bathroom modern farmhouse style home offers exceptional indoor and outdoor living with an expansive covered porch, pergola, grill kitchen, and hot tub overlooking the links of the Copake Country Club and the lake beyond. Full of amenities and activities, kayak and stand up paddle on the lake from the nearby dock or visit the adjacent Copake Country Club for 18 holes of golf or a meal at the club house restaurant - The Greens. Would make a perfect seasonal winter rental as Catamount Ski Area is only 15 mins away. Clad in vertical cedar siding and a black standing seam metal roof, the handsome exterior facade is accented with stacked stone finishes. The home centers on an open concept floor plan with a gourmet kitchen with island seating, dining area bathed in natural light, and a living room with a gas fireplace. The spacious sitting room with games area has French doors out to the pergola with Adirondack chairs and a bench, well positioned for sunsets across the links. The main level has a generous guest suite with a full bath. A powder bath, pantry, mud room, and attached garage complete the main level. Upstairs, there are dual primary bedroom suites and two guest bedrooms. The main primary bedroom has custom built-ins and a luxurious bath with a freestanding tub and spacious steam shower. The finished lower level offers a custom built bunk bedroom, full bath, professional training gym, and media and recreation area with gas fireplace and banquette. About 95 miles north of New York City, this newly built and exceptionally stylish country house showcases the beauty and charms of the Copake Lake lifestyle in any season. Pls note summer rate is $28k/month

Luxurious Salisbury Summer Retreat - $75,000/term: May 25, 2024 - Sept 3, 2024, or $30,000/month: June, July & August 2024 - Escape to the epitome of luxury and tranquility in the heart of Salisbury, Connecticut. This architecturally designed 9,000 sq. ft. home with pool, set high on a hill of rolling lawn, offers breathtaking views of the Housatonic River Valley and Taconic Mountain Range - the perfect backdrop for stunning sunrises and sunsets. Spread over four floors, this magnificent retreat boasts 7 bedrooms and 9 baths, providing ample space for family and friends. The well-appointed kitchen with generous eat-in space is ideal for preparing and savoring meals, while the adjoining covered porch invites you to dine al fresco amidst nature's splendor. The first floor features sun-drenched common areas with soaring ceilings, including a grand dining room, expansive living room with two fireplaces, a serene sunroom, and a cozy den/TV room - offering an abundance of space for relaxation and entertainment. The second-floor landing boasts an inviting common seating area with oversized windows, a sublime spot to unwind and appreciate the surrounding beauty. The luxurious Primary Bedroom Suite serves as a private oasis, complete with a sitting room, office, and two fireplaces. Additional bedrooms on the second and third floors ensure comfort and privacy for all guests.

Cozy and chic on a quiet, country road in Copake! This charming, 2 bed/2 bath cottage rental is nestled under a soaring pine tree and tucked behind a thick hedge of flowering forsythia. Lovingly updated, the home boasts: open kitchen with a sunny, bay window looking out at nature...living room with a modern wood stove and beamed ceiling...renovated, modern baths - one with a two-person, glass-enclosed tiled shower & the other with a soaking tub...wide-plank floors...second-story office nook...washer/dryer...landscaped and fenced rear yard with a deck and potting shed...and a spacious, covered front porch. Pets are allowed with owner's approval and an additional deposit. Easy access to the Taconic State Parkway. And ideally situated right between the two bustling, town centers of Hudson and Great Barrington with all their restaurants, cafes, shops and galleries - +/-25 minutes to each.

Nestled in the picturesque landscape of Ancram, New York, Herondale Farm offers a serene getaway with its charming 3-bedroom, 2-bath farmhouse. This 1800 square foot home is fully furnished, featuring light-filled rooms, polished wood floors, and a cozy AGA stove-equipped kitchen. The main floor bedroom and propane woodstove add to the home's rustic appeal, while the large covered front porch invites peaceful afternoons overlooking the pastoral surroundings. Accommodating guests is effortless with the beautifully designed 1-bedroom apartment above the 3-car garage, boasting 1500 square feet of space, wood floors, cathedral ceilings, and a kitchen. The apartment's bathroom and expansive views encapsulate the tranquil essence of country living. Herondale Farm, known for its natural healing products and services, becomes a hub of activity from Memorial Day to Labor Day, making it an ideal time for a rental. Whether seeking a summer retreat or a unique living experience, this property promises a blend of comfort and elegance amidst nature's beauty.

This meticulously maintained Salisbury charmer is what you've been waiting for in a rental home. Move right in for the academic year. Available September- June. When you can chose to work from anywhere, why not work from this private country location, yet moments from the center of town. With highspeed internet, and a private office space you can easily work from home, and step out on your lunch to enjoy all of the hiking trails just minutes away. Fully furnished 4 Bedroom 2.5 bathroom, plenty of room for family and friends. Tastefully renovated with high-end everything including, internet, cable, appliances, full house Sonos speakers. All bedrooms have their own television for ultimate privacy and downtime away from it all. Ensuite primary bedroom is secluded on it's own floor. Three additional bedrooms share a large bathroom on the second floor. Close to: hiking, lakes, arts & cultural events, Berkshire School, Salisbury School, IMS, Hotchkiss

SUMMER RENTAL AVAILABLE JULY 1st-August 31st . Are dreaming of a rental in the country with a pool? This meticulously maintained Salisbury charmer is what you've been waiting for. Bring nothing but your friends, family and laptop. Work from this private country location, yet moments from the center of town. With highspeed internet, and a private office space you can easily work from home, and step out on your lunch to enjoy all of the hiking trails just minutes away. Spend the summer swimming in spectacular Twin Lakes, and family friendly, Lakeville Lake. Fully furnished 4 Bedroom 2.5 bathroom, plenty of room for family and friends. Tastefully renovated with high-end everything including, internet, cable, appliances, full house Sonos speakers. All bedrooms have their own television for ultimate privacy and downtime away from it all. Ensuite primary bedroom is secluded on it's own floor. Three additional bedrooms share a large bathroom on the second floor. Come work and play this summer from the seclusion and serenity of the country setting. Available July 1st-Aug 31st . Close to: hiking, lakes, arts & cultural events.

Idyllic 3-Story Guest House with Views - This perfect contemporary cottage with gorgeous mountain views on a quiet and beautiful country road is now available to rent from August 2024 for $6000 and September 2024 for $5000. Enter the first floor to a sitting room that opens up to an en-suite bedroom with a washer and dryer and a screened porch. Enjoy the second-floor views with dramatic double-height ceilings in the living space that's open to a well-appointed kitchen. The second floor is completed by a full bath and porch that is perfect for sitting in the sun or dining outside. The 3rd-floor bedroom has a king-sized bed.

A Tranquil Retreat Surrounded by Nature. Rhoda Pond: Fully furnished. 4 BR 32 BTH. A three-season, 16 x 21 screened porch. Private community, w/ access to a common area with a dock and beach. The rental includes a skiff equipped with an electric motor, community Tennis Court, and more. Great things about this home and location: 1. Beautiful clear swimming lake 2. Great fishing. 3. Great for quiet strolls around the community. 4. Your own boat with an electric motor, canoeing and kayaking 5. Right outside your door, the best biking in the East plus 25-mile HVRT 6. Excellent equestrian facility nearby 7. 2 tennis courts 8. Softball field 9. Minutes from skiing 10. Active pickleball community 11. Great aerial Park and longest zip line in America 12. Bash Bish Falls 13. More and varied restaurants than one can count 14. Access to a famous working dairy farm. 15. Many local farmers markets 16. Short trip to Hudson, Great Barrington MA Tanglewood, Sharon CT. 17. Many local music venues 18. Orvis shooting school 19. Room for vegetable garden