Vacation rentals in Lenox

Cottage in Great Barrington

A charming cottage exterior is framed by lush greenery and vibrant flowers. The inviting red door is adorned with a decorative wreath, while large windows display rustic charm. A wooden fence adds an element of privacy, complementing the tranquil setting of this quaint getaway.

4.94 out of 5 average rating, 294 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Superhost

A bright and airy entryway features multiple windows that allow natural light to pour in, illuminating a white chair and a wooden bench. A wall mounted coat rack is visible, adding a practical touch to the welcoming space.

4.93 out of 5 average rating, 231 reviews

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

4.96 out of 5 average rating, 24 reviews

A covered outdoor seating area features a light wood ceiling and walls, surrounded by nature. A comfortable sectional sofa with bright cushions is complemented by a glass coffee table. Warm light fixtures hang above, enhancing the space's cozy atmosphere while large windows invite the greenery outside.

Cabin in Stockbridge

Stockbridge Snug- cabin luxury just steps to lake!

The Snug (an energy efficient home) was designed, renovated, and completed in June 2022. It serves as a cozy 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, attend a Tanglewood concert, take in a play, or just hot tub amongst the trees- we hope you enjoy your stay and will visit us again.

A modern kitchen is illuminated by natural light filtering through a large window. Gray cabinetry and stainless steel appliances are complemented by white countertops. Wood beams stretch across the ceiling, adding a touch of warmth to the sleek design. A cozy rug is placed on the hardwood floor.

4.93 out of 5 average rating, 234 reviews

The Berkshire Quintessential Cape downtown Lenox

Experience the best of the Berkshires in this charming, in-town, Lenox home! With stunning oak floors and white walls, this light-filled gem features high ceilings and abundant windows. Enjoy a cozy first-floor bedroom and full bath, while upstairs hosts two spacious bedrooms with a shared bath. The open-concept living and dining area, complete with a wood-burning fireplace, is perfect for gatherings. Just a short stroll to town, Tanglewood, and Canyon Ranch, this is your ideal getaway!

4.94 out of 5 average rating, 36 reviews

A serene outdoor space features a circular pool surrounded by a stone patio. Lounge chairs sit nearby on a grassy area, and a grill is positioned under a wooden pergola. Lush trees provide a natural backdrop, enhancing the tranquil setting.

Guest suite in Richmond

Berkshire Mountain Retreat

Studio apartment with private entrance nestled in bucolic Richmond. Located on a quiet mountain road adjacent to miles of hiking and biking trails. Close to 4 ski areas and minutes to Tanglewood, Kripalu, Clark Art Museum, Mass MoCA, Hancock Shaker Village, the Mass Audubon Wildlife Sanctuary and more. A short drive to Lenox, Stockbridge, and Great Barrington where shopping and fine dining await. Your relaxing vacation begins here with an expansive yard, views and in ground pool!

A spacious kitchen features modern appliances and abundant natural light. An island with seating for four is highlighted by stylish pendant lighting. The cabinetry is light-colored, complementing the tiled floor, while large windows provide views of the outdoors.

4.88 out of 5 average rating, 161 reviews

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Spacious 4-Bedroom Retreat in Lenox, MA Experience your perfect getaway in this beautifully renovated home in Lenox, MA. This charming 4-bedroom, 3-bathroom retreat offers 2,089 sq. ft. of space and is designed for a comfortable stay. The deck, BBQ grill, and cozy seating make for memorable gatherings. The Wi-Fi is fast for all your streaming needs, and there are 2 Wi-Fi HDTVs. Lenox, MA, is a picturesque town in the heart of the Berkshires. Book your stay today!

4.99 out of 5 average rating, 216 reviews

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

4.95 out of 5 average rating, 274 reviews

A wooden dock extends into the calm water, shrouded in a gentle fog. Neatly placed wooden planks create a sturdy path, while faint hues of seasonal foliage can be seen along the edges, adding a touch of warmth to the serene landscape.

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

4.93 out of 5 average rating, 374 reviews

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guesthouse in Stockbridge

The kitchenette features modern black cabinetry, open wooden shelves, and a sleek countertop. A microwave and a compact oven are included, along with a sink below a skylight. Glassware, jars, and dishware are neatly arranged along the shelves, enhancing functionality and style.

4.95 out of 5 average rating, 234 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

4.97 out of 5 average rating, 67 reviews

A compact laundry area features a stacked washer and dryer in sleek stainless steel, positioned near a door that leads outside. Natural light filters through the glass panes of the door, creating a bright and functional space.

Apartment in Lenox

Main Street Delight - One Bedroom Apartment

Located on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a Smart 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.

5 out of 5 average rating, 35 reviews

A lush garden area features a serene fish pond surrounded by various greenery, including vibrant shrubs and tall trees. The natural stone pathway leads around the pond, while a low stone wall provides a sense of enclosure to the tranquil setting.

Guesthouse in Lenox

Guest House at Stonover Estate

Located on historic Estate grounds, this is an aesthetically pleasing and private getaway for adults and couples. The town of Lenox hosts multiple 5-star restaurants, and the property is a 10 minute walk to town. It is 1 mile from Tanglewood, 1 mile to Shakespear & Co., and 14 miles to Jacob’s Pillow. If you like the outdoors, it is a half mile to Kennedy Park for hiking or biking.

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Popular amenities for Lenox vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Lenox

5 out of 5 average rating, 28 reviews

A charming red cottage surrounded by lush greenery is depicted. An inviting front porch with a decorative entryway features potted plants. A stone pathway leads to the house, showcasing an array of colorful flowers and shrubs that enhance the natural setting.

Guesthouse in Lenox

Bella Rena Guesthouse

4.94 out of 5 average rating, 34 reviews

A spacious sitting area features a comfortable brown sofa, positioned beside large glass doors that open to a deck view surrounded by greenery. Wooden beams highlight the ceiling, while shelves display books and decorative items, enhancing the cozy ambiance.

Cottage in Stockbridge

Quiet 2 BR cottage in the heart of the Berkshires

4.96 out of 5 average rating, 67 reviews

An open living area features warm wooden flooring and high ceilings with exposed beams. Two plaid armchairs sit across from a cozy sofa, accompanied by a small table. Large windows provide views of the surrounding greenery, and a doorway leads to the outdoor space.

Cottage in Lenox

The Jaynes House ~ Cozy Lenox Retreat

A coffee station is presented on a patterned granite countertop. A sleek coffee machine is positioned beside a glass carafe, with a selection of coffee and tea pods neatly arranged in a small tray. Two mugs with colorful designs rest on decorative coasters.

4.96 out of 5 average rating, 26 reviews

The Aviary

Cottage in Great Barrington

A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.

4.94 out of 5 average rating, 133 reviews

The Cottage at The Barrington House

Cabin in West Stockbridge

A newly-renovated cabin is nestled among tall trees, surrounded by vibrant green grass. The structure features a spacious porch that overlooks the natural landscape, enhancing the sense of tranquility provided by the Berkshire woods.

4.99 out of 5 average rating, 98 reviews

Cozy, two-bedroom cabin in a wooded glen

5 out of 5 average rating, 77 reviews

The serene lakeside views feature a wooden dock surrounded by lush greenery. Two Adirondack chairs and a small table are positioned near the water's edge, inviting relaxation. Gentle sunlight reflects off the calm water, framed by the branches of a large tree.

Loft in Lee

Lovely Loft on Laurel Lake