luxury houses for rent Great Barrington, United States

August 2023 - Hip 1820 country home with Scandinavian interior design touches. The living room and the den with fireplace have both an abundance of natrual light from south facing windows. Dining room leads to a brick patio from where your eyes can wander the land. Large eat in kitchen with ample pantry and laundry. Fantastic screened in porch overlooks a large pool with bountiful vegetable gardens. Lovingly cared for property offers lavish space with 3 more guest bedrooms, office area and two full baths upstairs. Mainly wood flooring and lots of natrual light fill this gracious home. Truly a Berkshire retreat for everyone to enjoy.

VACATION PERFECTION! Look no further. This spacious and comfortable 5 bedroom, 3 1/2 bath home has it all. A pool, a tennis court, panoramic distant and scenic views, and it is in close proximity to two of the more popular Berkshire County restaurants. Don't want to eat out? Enjoy this home's large and attractive cook's kitchen. Fully available as of August 1st for $30,000 plus utilities. The rent per month for September 2026 through June 2027 is $10,000 per month.

Over twenty five scenic acres with beautiful mountain views abound this newly renovated 4 bedroom cape. Located minutes from Great Barrington and Stockbridge this immaculate home has three levels of living. Enjoy the spacious open deck for outdoor grilling or your screened-in deck for dining with picturesque sunny views. Large three car garage. New pool installed for summer season 2024.

This stunning mid-century 3-bedroom, 3.5-bathroom house is indeed a hidden gem nestled in the sought-after village of Mill River. Offering a harmonious blend of tranquility, luxury, and convenience, this property promises an unparalleled living experience. Upon entering the grounds, you'll immediately be captivated by the picturesque setting. Sunlight filtering through the woodlands casts a gentle glow over the meticulously manicured gardens, creating an oasis of complete privacy and serenity. The home itself is a masterpiece of modern design, exuding elegance and sophistication at every turn. Each of the three spacious bedrooms boasts its own newly renovated en-suite bath, ensuring comfort and privacy for residents and guests alike. Additionally, a versatile sunroom offers the flexibility to serve as additional guest space or a cozy retreat for relaxation. At the heart of the home lies a double-sided stone fireplace, which serves as both a focal point and a source of warmth and comfort for cooler evenings in the open-plan kitchen, living, and dining area. This seamless integration of spaces fosters an inviting ambiance, perfect for gatherings with loved ones or simply unwinding after a long day. Moreover, the property boasts additional amenities such as a Steamshower, outdoor sauna, high-speed internet and is pet-friendly, enhancing the overall living experience. In summary, this exceptional property offers a rare combination of elegance, comfort, and convenience, making it the ultimate retreat for enjoying the summer months in the idyllic village of Mill River. Whether you seek a peaceful sanctuary or a stylish space for entertaining, this home is sure to exceed your expectations and provide an unforgettable living experience.

Fully renovated, 2000 square feet, roomy 4 bedroom, 2.5 bath home located centrally to all the best of the Berkshires has to offer! Large, sunny yard, sunroom, deck, minutes away from Laurel Lake with access to private town beach with lifeguards and volleyball. Huge sunny primary bedroom with office nook and ensuite full bath. Wolf steam ovan, Bertazzoni 6 burner stove. Dishwasher, washer/dryer available. Charming sunroom, deck with fairy lights and large yard with curated veggie garden. Two queen beds, one full bed, two twins. 5G fast internet.

Summer rental July & August $12,000/ month - 3 Bedrooms and 2.5 Baths Lenox home close to downtown Lenox and Lee. Open kitchen/ dining area with gas fireplace. The livingroom has a comfy sectional and a large TV. There is also a great sunny family room with access to a deck with dining table and BBQ. The main bedroom has a private bath and the other two guest bedrooms share a full bath. The lower walk out level is designed for entertainment, TV & pool table and has a nice field stone fireplace. Close to downtown Golf, Tennis, Miraval Spa and within minutes to Tanglewood, Shakespeare & Company.

Charming farmhouse, built in 1860, thoughtfully modernized for comfortable indoor–outdoor living. Set on 5 picturesque acres, the property features an original barn and a natural spring-fed pond, creating a serene country setting. The first floor offers a light-filled, open-plan kitchen and living room anchored by a large wood-burning fireplace. French doors open to a stone terrace and pergola, perfect for outdoor dining and relaxed entertaining. Upstairs, you'll find three inviting bedrooms, an upstairs living room with a gas fireplace, and French doors leading to a second stone terrace. A cozy "sunset porch" captures sweeping western views of the Catskills—an ideal spot to unwind at the end of the day. Located just 5 minutes from the Hawthorne Valley Farm Store, 15 minutes from Chatham and Hillsdale, and 25 minutes from both Hudson and Great Barrington. Only 20 minutes to Catamount and other Berkshire ski areas. In addition, there are three conveniently located private schools : Hawthorne Valley Waldorf School, Darrow School, and Woodland Hill Montessori School. Lawn and landscape care, snow plowing, and the dedicated attention of long-standing property caretakers are included, ensuring the home's upkeep.

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.

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 2027. June: $5,700/month July: $8,550/month August: $8,550/month September: $5,225/month No pets.

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.

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

$7000 per month for an Academic year lease. This unique waterfront rental, with an expansive deck & beautiful vista has a Main Residence with 3 bedrooms, 3 full en-suite baths, large stone fireplace & includes a one bedroom Guest Cottage with kitchen, full bath & a lovely stone fireplace. Available for $7000/month for an Academic year lease (Labor day 2026-Memorial Day 2027), a $7000/month winter lease term can be negotiated, or $8500/month for a one year lease. The setting is private, both houses have high ceilings & are light filled with open floor plans. Entertain right at the lakeside gazebo, on the large wrap around deck or lower patio. The lower level of the main house has a large family room with a pool table & a walk out for a stroll down to the lake where you can swim, kayak, sail, fish on Connecticuts' deepest lake. Enjoy all that our Litchfield Hills, Berkshires & Hudson Valley have to offer, including a variety of cultural events, ( Sharon Playhouse, Tanglewood, Jacob's Pillow, Music Mountain, The Movie House), country fairs, farm markets, & restaurants with farm-to-table fare. Private & Public schools, medical facilities, riding stables, hiking the AT, skiing, shopping, all nearby. Aprox 1.5-2 hrs to Bradley International & NYC airports respectively. 4 Bedrooms & 4 baths count include both houses.

"Glimmerglass" offers the ultimate Academic Year retreat in an enchanting 4 bedroom waterfront home, available now through June 12, 2027. Nestled in a wonderfully private, serene setting with breathtaking water views, this exceptional property is designed for both restful getaways and effortless entertaining. Inside, the inviting layout boasts a seamless kitchen and family room combination alongside a large sunroom where dawn paints shimmering light across Lakeville Lake. The spacious living and dining areas are anchored by a cozy fireplace, where the quiet magic of the seasons unfolds. Outside, step directly onto your private dock, where misty autumn mornings give way to crisp, starry winter nights and the soothing silence of nature. Though deeply private, the home is ideally situated just minutes from the charming villages of Lakeville and Salisbury, CT, as well as Millerton, NY, keeping local boutiques and fine dining well within reach. No pets allowed. The Rail Trail in Millerton is great for walking and biking, while the Appalachian Trail is just up the road. NYC train service is only a 20-minute drive away. For winter sports enthusiasts, the location is unbeatable-offering convenient proximity to premier regional skiing: Mohawk Mountain, Catamount Ski Area and Butternut Ski Area. Close to area private schools: Hotchkiss, Indian Mountain School, Berkshire, Kent, and Millbrook School.

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.

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.