luxury real estate for rent Great Barrington, United States

Escape the city heat and spend August in an unbeatable, walk-to-town Stockbridge location. This striking, artist-loft-style residence perfectly blends vibrant, colorful design with modern country comfort. Situated just a short stroll from historic Main Street, it offers a sophisticated, high-design summer sanctuary. Enjoy radiant heated, polished concrete floors, expansive ceiling height, and open loft style living. Featuring 1BR, en-suite with soaking tub and walk-in shower. There is even another full bath for guests, and garaged parking. The kitchen is fully equipped to enjoy cooking up the Berkshires summer bounty. This rental is available from August 1 - September 1 for $10,000 - all inclusive! You won't find a more unique, stylish, or beautifully curated space to spend your Summer!

This private, light-filled mountainside retreat is a gem. Tucked off of Webster Road, with partial views to magical Tyringham Cobble, it's barely 10 minutes to Lee and Stockbridge. Large windows bring in the serene surroundings. Double height living/dining room features propane fireplace and wall of built-ins. Renovated kitchen opens to sunroom with French doors to mahogany deck and gardens. Beyond that, wooden steps lead to a deck overlooking a beautiful stream. Mudroom, half bath, and plenty of storage complete the first floor. Upstairs, find two lovely bedrooms, renovated bathroom with laundry, and unique balcony overlooking the living area. While there's no reason to leave this idyllic property, the best of the Berkshires is moments away.

Perfectly located within 10 minutes to Tanglewood, this all one floor ranch home is fully furnished and nicely appointed. The Galway Court neighborhood experiences limited traffic situations while making the trip to the center of Lenox and its shops and restaurants an easy bike ride for anyone so inclined. Like to golf? The Miraval Country Club is just five minutes away. The house features a very nice screened porch and the property encompasses a landscaped three-quarter acre lot. This is a must see rental to be fully appreciated.

Experience the ultimate August in Lenox! This lovely cottage is available to rent from August 1 - September 2, offering a prime location just minutes from downtown and Tanglewood. Inside, enjoy a light-filled spaces and cozy proportions. This 2-bed, 1-bath retreat features a first-floor bedroom, bathroom, and washer/dryer. The second bedroom is a loft. Relax on deck and enjoy the sounds of nature. Key Features: All-Inclusive: $12,000 per 32 day period covers all utilities. Garaged parking for 1 car. Turn-Key: fully furnished-just bring a suitcase! Please note: there is no shared driveway to access the property.

Wow! You must see to fully appreciate how special this home truly is. The construction quality is not only exceptional, but it is also new this year. The open floor plan log home features impactful vaulted ceilings, a spacious eat-in kitchen and pantry, a bright dining area, and an eye-catching Great Room with an effective wood burning stove. Four attractive bedrooms, 3 1/2 bathrooms, an office area, and a lower level game room all add to the enjoyment of this outstanding property. Like to ski? Fairly close to several ski areas. The rental period availability runs from December 15, 2025 to March 15, 2026.

Nicely renovated and beautifully furnished Colonial rental located in the heart of Otis. The updated eat-in kitchen is enhanced by attractive wood floors that exist throughout the home. The bathrooms, the propane furnace, and the windows have also been updated. The town has provided high speed broadband service throughout the community so if you need to work from home, the required technology is at your fingertips. Otis Ridge ski area is very close by. A post office and a bank are also nearby. Tanglewood, Jacob's Pillow, and numerous other Berkshire attractions are all located within a half hour of this rental. Schedule a showing now. The rent during July and August is at $3,000 per month. The rent during the other months of the year is at $2,750 per month.

Opportunities are right outside your door. Cool off in the community swimming pond after playing a few games of tennis on the two clay courts or after taking a hike within the community. Come back to the tastefully-designed main home, perfect for friends, with an open plan kitchen/living space with 3 bedrooms. The stunning attached conditioned barn with grand vaulted ceiling and rustic wood is the perfect gathering space with a sleeping loft and bathroom above. Surrounding the house are impeccably maintained grounds with a stone patio and walkways along with luscious perennial gardens and lawn. Perfectly located in a country setting, but convenient to all that the Berkshires has to offer. Minutes to Lee, Great Barrington, Stockbridge, and shopping.

Fantastic, adorable 2/3 bedroom cottage in the heart of Lakeville with direct access to the lake via the backyard. Mowed path leads to the town grove where there is swimming, lifeguard, snack bar, boat rentals, and paddle tennis. Large windows on the back of the house take advantage of year-round views. Small back porch to relax on when you come back from a day swimming or kayaking. Barbeque in the backyard or take an easy stroll to Lakeville's many restaurants, coffee shops, pizza parlors, bookstore, or just amble around town after dinner. A finished basement with double bunk beds and French doors leading to the yard allows for overflow guests. Available July and/or August 2026, as stated in the listing

Spend your summer on the shores of Greenwater Pond in this peaceful Berkshire waterfront retreat. Offering beautifully designed living spaces, serene water views, and a private dock, this is the perfect setting for long summer days spent kayaking, boating, entertaining, or simply unwinding by the water. The property also offers convenient access to the public boat launch on Greenwater Pond, making it easy to enjoy everything the lake has to offer. Thoughtfully designed for comfort and relaxation, this home provides an ideal escape while remaining within reach of the Berkshires' renowned dining, culture, and outdoor recreation. Available June, July, August, and September 2026. June: $6,000/month July: $9,000/month August: $9,000/month September: $5,500/month No pets.

A Sweet and Sunny antique available for the Spring (mid-May thru July 1) and/or Academic Term - Set on 1.4 acres along a desirable road in Lakeville, this 1700s home perfectly blends modern comforts with historic character. Step inside to find three bedrooms and two bathrooms across two floors. The living room, anchored by a massive hearth, is the center of the home. The galley kitchen, with an adjoining mudroom, offers plenty of storage and opens to the outdoor deck- perfect for dining and entertaining. A cozy den and the option for a first-floor primary suite with an en-suite bathroom complete the main level. Upstairs are 2 light-filled bedrooms and a spacious full bathroom. The original details and hardwood floors throughout the home add warm and rustic charm to this bright and airy home. Conveniently located minutes from local private schools and easy access to Salisbury, 30 Indian Mountain Road is the epitome of effortless country living.

A Sweet and Sunny antique available for the Academic Term - Set on 1.4 acres along a desirable road in Lakeville, this 1700s home perfectly blends modern comforts with historic character. Step inside to find three bedrooms and two bathrooms across two floors. The living room, anchored by a massive hearth, is the center of the home. The galley kitchen, with an adjoining mudroom, offers plenty of storage and opens to the outdoor deck- perfect for dining and entertaining. A cozy den and the option for a first-floor bedroom with an en-suite bathroom complete the main level. Upstairs are 2 light-filled bedrooms and a spacious full bathroom. The original details and hardwood floors throughout the home add warm, rustic charm to this bright, airy home. Conveniently located minutes from local private schools, the center of Salisbury, and all that Litchfield County has to offer.

Enjoy lake living on beautiful Lake Wononscopomuc. This beautifully maintained 3-bedroom, 2-bath home is set on 2.9 lush acres in coveted Lakeville, offering 150 feet of private lake frontage. An ideal academic-year retreat, the property combines privacy, comfort, and convenience with the area's esteemed private schools. The main level features a cozy, well-appointed living room with an electric stove, a fully equipped kitchen with an eat-in island, and an adjoining dining room. A light-filled, 3-season sunroom with a vaulted ceiling overlooks the lake and is the perfect space to dine or relax with a view. The main floor is complete with a spacious bedroom with a queen-size bed and a full bathroom. A second full bath and two additional bedrooms make up the second floor; one with two twin beds and the other with a queen bed. Outdoors, the property offers exceptional space to unwind and enjoy the natural surroundings by the lake. The porch is outfitted with outdoor dining furniture and comfortable seating. A stone patio creates a quiet retreat, while 150 feet of waterfront and perfectly placed Adirondack chairs offer a serene lakeside setting throughout the seasons. Centrally located amidst local private schools and just minutes from the center of Salisbury, the home provides easy access to local shops, dining, and year-round outdoor recreation, including boating, hiking, skiing, and golf. Also available for the Summer Season, MLS #24157054

Rustic Chic Barn, renovated as an energy efficient home, consisting of 2 large open floors w/ a Queen Bed on 1st floor, and 2 more Queen Beds on the 2nd Floor. A group, or two couples should be comfortable sharing this unique space. Fully equipped kitchen w/gas stove, washer & dryer. There is a separate toilet with sink, and a single shower with sink. Radiant floor heating throughout. Full music set up w/instruments & PA on 2nd floor. 1GB Wifi, smart thermostat, smart lighting, AC window units on each floor, 2x 42' TV w/firestick & cable. There is also a full house Auto-Backup Generator. Ambient light moves through the building during the day & no artificial lighting is needed. Excellent star gazing, with spectacular views of the Milky Way on a clear night. Circular driveway lined with Apple Trees leads to a large stone patio w/BBQ as well as an above ground fire pit. Summer guests have access to a canoe, blueberry, peach and apple groves, as well as a Lakeville lake facility and parking pass. The Hotchkiss 9 hole golf course is 1 mile away. Winter guests have 3 local ski resorts 30-45 minutes away plus a ski jump in Salisbury. Hotchkiss, Indian Mountain, Salisbury private schools, Lime Rock Park Racetrack & cultural activities & shopping in Millerton, NY are all within a 5 mile radius. Privacy, amazing marsh views w/abundant bird watching, wildlife, country living, comfort & convenience awaits you. Field Card states 1 Bedroom, there is a Bed on the first floor & 2 Beds on the 2nd floor - open floor plan

SEASONAL RENTAL - LAKEVILLE ESTATE - September 15th - April 1st Experience the timeless elegance of this 1827 antique home on a spectacular 22-acre private estate. This sensational property blends historic charm with modern convenience in the coveted Lakeville/Lime Rock area. Throughout, you'll find ample windows providing radiant natural sunlight, and stunning, wide-plank hardwood floors that speaks to the home's rich heritage. There is a cozy sitting room in the open country kitchen area, modern appliances, and an adjacent formal dining room as well as a downstairs 1/2 bath. Upstairs are 4 generous bedrooms including a primary suite with fireplace & full bath offering both a stand alone shower & antique tub. Three additional spacious bedrooms share a full bath, & there is an office area upstairs. The well situated fireplaces create warmth and ambiance perfect for the seasonal months. The expansive grounds include multiple barns and a beautiful pond seen from the magnificent sun room. This rural sanctuary provides seclusion while maintaining easy access to area amenities, ski resorts, restaurants and many entertainment options, as well as several prestigious private schools close-by. The perfect retreat for those seeking authentic New England charm and serenity for the winter months.

Millerton, NY — Fresh, modern ground-floor living with village convenience Be the first to enjoy this gut-renovated (2023-2024) ground-floor, walk-out apartment set on a one-acre village lot. Oriented toward a beautiful ridgeline just above the Harlem Valley Rail Trail, the home captures year-round sunset views. A covered porch/mudroom entrance keeps rain and snow outside, while a second entry opens to a central hallway that connects the kitchen, living room, and bedroom for an easy, practical flow. The kitchen is crisp and functional with a brand-new gas range and vent hood, new flooring, and ample cabinetry for pantry and storage needs. The fully rebuilt bathroom features a vanity with integrated storage, new lighting, and a sleek glass corner shower. In the bedroom, you'll find brand-new floors and windows, newly installed heating, and a double-insulated exterior door to enhance comfort and efficiency throughout the seasons. A detached garage is included and is perfect for bicycles, seasonal gear, or an outdoor maker space. From the property, it's an easy three-minute walk to Millerton's corner amenities—a diner, pizzeria, tea house, Chinese restaurant, florist, and consignment shop—and just a few more minutes to boutiques, additional restaurants, art galleries, a coffee shop, movie theater, library, CVS, bank, and a gas/convenience store. This is a strictly non-smoking property, ideal for one or two occupants seeking a turnkey home with storage, sunsets, and an effortless village lifestyle.