Vacation rentals in Lenox

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Berkshires Zen | Mountain Views & Private Porch

Discover pure serenity in this modern, zen-inspired 2-bdrm guesthouse on historic 1738 property. Whether you’re here for world-class music, wellness retreats, hiking, or simply unplugging amid rolling hills, this sun-drenched sanctuary feels like your own private escape. What you’ll love: • Private entrance + spacious back porch with panoramic views • 2 comfortable queen beds • Luxe bathroom w/ rain shower, his/her sinks, deep soaking tub • Central air, in-unit washer/dryer • 55” Smart TV

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

Historical Downtown 1 Bedroom Apartment

Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

Lenox Cottage

Tucked away, yet one block from town is our quaint Lenox cottage. This space is perfect for 2 couples, a small family, or even a solo traveler looking to enjoy all the Berkshires has to offer. We are a block from historic downtown Lenox with shopping, wonderful dining and cafes. 1.5 miles to Tanglewood 2 miles to Kripalu Close to all of the theater groups 25 min drive to Jacob’s Pillow

Stylish Berkshires Retreat

Escape to our modern 2-bedroom retreat in the heart of the Berkshires! This stylish, centrally located home comfortably welcomes up to 4 guests. Perfect for a relaxing getaway or adventurous holiday, it features a fully equipped kitchen, a dedicated workspace, and easy access to Tanglewood, ski resorts, and Lake Laurel. Your ideal home base for exploring all the Berkshires has to offer.

Eliza Suite

Recently redecorated, new bed & hybrid memory foam mattress. 😍 Charming 1-bedroom apartment in a beautifully maintained Victorian home, located in the heart of town. Enjoy high ceilings, period details, and modern comfort just steps from shops, cafes and local attractions. Ideal for anyone looking to enjoy the convenience and character in a vibrant, safe and walkable neighborhood.

Lovely Berkshire Apartment. Private & Peaceful

Kick back, relax and rejuvenate in this spacious, calm, stylish, zen space just minutes from town. Private entrance with keyless entry. Comfy crisp clean beds and spacious living room. Kitchen has everything you'll need to cook dinners or not! Friends getaway, couples, familes or remote work. Beautiful sunsets! Minutes to Tanglewood/Jacobs Pillow