luxury houses for rent Berkshire County, United States

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.

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.

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.

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.

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.

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.

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.

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 rental home, this listing should be Option #1. The famous real estate saying about location, location, location could have this property as its photography definition. Already rented for July/August 2025 at much higher rates.

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.

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.