Holiday rentals in North Canaan

Luxury/pool/private Villa Mariana Blackberry River

Charming and spectacular colonial in every single detail. Modern and rustic interior at the same time. Enjoy the comfort of the most entertaining place with a beautiful family room, custom designed master chef kitchen, bar area 2 dining areas, formal living room, and laundry with half bathroom. 1 en suite on the 1st floor. 2nd floor has a primary bedroom with walking closet and a fantastic bathroom, 2 more bedrooms and another bathroom . You will refresh and will feel the peace of nature.

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

Bull Hill Bungalow

Relax with the whole family at this peaceful, cozy home. Set on five acres located in the lovely Berkshires. Walk, bike, and hike the trails, ski Butternut and Catamount, rent a pontoon boat at nearby Twin Lakes, and explore the many great restaurants in Great Barrington and Salisbury. Immerse yourself in the culture. Tanglewood, Jacobs Pillow and many theaters are nearby. When in season, you can pick fresh vegetables from the garden, fruit from the fruit trees, and berries from the bushes.

Cozy Canaan Home near Lime Rock, Newly Renovated

The whole group will enjoy easy access to everything from this centrally located place. Located in downtown North Canaan within walking distance to town. Close to Berkshire, Hotchkiss, Salisbury, Indian Mountain and More. Family vacations or short visits. Lime Rock Park is close by. This 1802 historic house has been fully renovated but still has it's charm. Beautiful pine floor boards, and out door space for cooking, your stay here will be most enjoyable. New trundle bed & downstair cot added.

Scenic Berkshire retreat near Great Barrington

Kick back and relax in this calm, private, stylish hilltop lair. Unwind on the large front porch while taking in the expansive, beautiful landscapes that the Berkshires have to offer. A short drive to the Appalachian Trail, as well as local favorites like Bartholomew’s Cobble and Gedney Preserve. Afterwards, relax at nearby Umpachene Falls with its gracefully loping flat rocks making it ideal for sunning. Take a short trip (15 min) to the charming town of Great Barrington for shopping/dining

Stay in Downtown Canaan

This light-filled space with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. WELL BEHAVED dogs are welcome. Poop bags are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK to see what our area offers!!!

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town , pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Family friendly house with fenced yard & fire pit

Hillside Haus is a modern house close to Catamount Mountain & Ski Butternut and Hotchkiss School. Enjoy high ceilings, a cozy fire pit, fenced yard, family-friendly amenities (including crib and high-chair), and fully stocked kitchen. Sleeps 6 comfortably, and includes an office space. Perfect for year-round getaways—ski in winter, hike and picnic at nearby lakes and campgrounds in summer. Quick drive to charming and vibrant Great Barrington for shopping, art, and restaurants.

The Cottage at Great Falls Luxury Getaway.

Spectacular artisan designed cottage on the banks of the beautiful Housatonic river. Located on a quiet residential cul de sac , no through traffic. Interior features plaster throughout, stone veneer and mosaic flooring and original artwork. Fully equipped kitchen, elegant dining room. Oversized soaking tub in master bath. 2 bedrooms, sleeps 4. Fabulous water and mountain views . Large outdoor deck overlooking the water, second small stone dining deck. wonderful gardens.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.