Vacation rentals in Lenox

5 out of 5 average rating, 25 reviews

Apartment in Lenox

Center of Lenox, cozy Apartment 2-bedroom

The whole group will enjoy easy access to everything from this centrally located duplex apartment. Less than 300 yards away, enjoy downtown Lenox. Featuring several fine dining options or stop by the local Heritage Tavern for pub food & drafts. Enjoy the local roastery at the Lenox coffee shop or experience the Haven cafe & bakery. Several shopping boutiques along the way or visit the Lee Premium Outlets shopping center only 5 miles . Come enjoy the Berkshires and experience the town of Lenox!

4.95 out of 5 average rating, 38 reviews

An open living space offers a view from the kitchen towards a cozy sitting area. A soft sofa is positioned near a sliding glass door, leading to a greenery outside. Light gray walls and a decorative rug enhance the room's calm atmosphere.

Apartment in Lee

Cute, Cozy and Comfortable apartment

This cute little apartment is perfectly situated minutes to Tanglewood, Kripalu, laurel lake and downtown Lenox. 20 minutes to Stockbridge , 30 minutes to Great Barrington. Enjoy easy access to everything Berkshire from this little pied a terre . Great spot for a nice walk , 10 minutes to great hiking at Kennedy park and Olivia’s overlook.Less than 15 minutes to skiing at Bosquet and 25 minutes to Butternut. Owner lives above . Located in the village of Lenoxdale in a quiet neighbor hood .

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, 26 reviews

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!

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, 219 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, 376 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

Superhost

The entryway features a white door with a window, adorned with a decorative wreath. A view of lush greenery and moss-covered rocks is visible through the open door, creating a connection between indoor and outdoor spaces.

Guesthouse in Lee

4.93 out of 5 average rating, 15 reviews

The Blue Jay Cottage

RaquelRating, 5 stars3 months ago

The Blue Jay Cottage was the perfect place for a quiet getaway. My best friend and I went for a girls weekend and were very happy with our decision. It was absolutely adorable inside and the fireplace was amazing. We came during a winter storm and the hosts were very kind and accommodating with shoveling, salting, and even offered us alternative parking. Perfect location to visit all the must see Berkshire towns. Overall great hosts and a wonderful place to stay.

4.87 out of 5 average rating, 46 reviews

A coffee station is set up on a wooden countertop, featuring a coffee maker positioned beside glass storage jars labeled 'SUGAR' and 'COFFEE.' A lightweight shelf above the counter holds additional kitchen items, contributing to the organized and functional space.

Home in Lee

Spacious & Family-Ready Home w/ Fenced Yard in Lee

MauraRating, 5 stars1 month ago

We had a great stay! Vinicius’s home was clean, conveniently located to explore the Berkshires and easily accommodated our party of four, plus a dog. The fenced-in yard came in very handy with the latter!

Guesthouse in Stockbridge

The cozy living area features wooden walls and shelving filled with rustic decor. A large set of windows allows natural light to fill the space, casting shadows on the light-colored floor. A comfortable seating arrangement includes two armchairs and a coffee table, creating a welcoming atmosphere.

4.93 out of 5 average rating, 30 reviews

Light-filled Carpenter's Cottage in Stockbridge

EvaRating, 5 stars3 weeks ago

The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!

4.97 out of 5 average rating, 34 reviews

Condo in Lenox

Spacious 3 bedroom apt in Lenox historic downtown

JamieRating, 5 stars3 weeks ago

Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

A stone arrangement serves as a rustic seating area, with several flat stones stacked for stability. The surrounding area features natural earth tones and scattered greenery, while a fire pit containing wooden logs is set in the background.

5 out of 5 average rating, 4 reviews

Spacious Guest House with Pool and Walk-in Shower

JessicaRating, 5 stars4 days ago

I loved my stay in the Berkshires at Siobhan’s place. The space was clean, spacious, and perfect for a quick work trip in the area. Fun walks right from the guest house and lots to explore in the area. Highly recommend!

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, 135 reviews

The Cottage at The Barrington House

GuillaumeRating, 5 stars2 days ago

We enjoyed very much our (unfortunately short) stay at Katie's cottage. It's a very cosy place and I felt that it looked much better in real than in the photos. The cottage that makes you feel at home instantly. It's very clean and all the products available and services are great. It is very conveniently located between all the main attractions areas and close to all the hikes. Katie was very responsive and communicative. We hope to come back soon!

5 out of 5 average rating, 6 reviews

A modern bathroom is shown with a glass-enclosed shower featuring marble-like tiles and a stone floor. A pedestal sink and toilet are positioned beside the shower. Natural light enters through a window, illuminating the clean lines and neutral color scheme.

Apartment in Lenox

Amadeus House-3 Bedrooms Each w Bath & Kitchenette

RachelRating, 5 stars8 months ago

We had a lovely stay at Marianne's place. The home is charming and located on a lovely street just a minute's walk to all the main shops in Lenox. The beds were comfortable with modern amenities. Would definitely recommend to those visiting the area.