Holiday rentals in Lenox

5 out of 5 average rating, 25 reviews

Flat 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, 39 reviews

Flat 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

4.93 out of 5 average rating, 232 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, 27 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.

Guest house in Great Barrington

4.95 out of 5 average rating, 126 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

4.94 out of 5 average rating, 36 reviews

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!

4.99 out of 5 average rating, 221 reviews

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

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

Guest house 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.

Guest house in Stockbridge

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

Flat 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

Guest house 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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Other great holiday rentals in Lenox

5 out of 5 average rating, 4 reviews

The Lenox Cottage

NicoleRating, 5 stars4 months ago

We had a very nice stay. It had pretty much everything we needed. Especially considering we cooked two of the nights and all the pans and utensils we needed were there. The decor was cool and the piano was a bonus for us. Only trouble I had was I have a very small car and had trouble getting up the drive with the snow we were having but that’s more environmental.

Cottage in West Stockbridge

4.97 out of 5 average rating, 34 reviews

Tanglewood Cottage in the heart of the Berkshires

LuRating, 5 stars10 months ago

This was our second stay here, and we will hope to be back again next year. Less than three miles from Tanglewood, plus nearby hiking trails & historic sites, the location gave us plenty to do. The home is sparkling clean, has lots of towels, pillows, etc. Screened porch, deck, heat & AC if needed. Barred owls call during the night. Hosts live next door beyond the trees. Excellent communication if needed.

4.95 out of 5 average rating, 235 reviews

Private room in Lenox

In town charming artist's home

KathleenRating, 5 stars2 weeks ago

Andrea was like a warm, welcoming friend the minute I met her. Her home was beautifully designed, with local antiques and her colorful paintings. I felt like I was in an Italian artist's villa. She gave me space to settle in but was also responsive and super-friendly. We shared breakfast one morning. Even though she was in the next room and there was a shared bathroom, I felt comfortable, welcomed and right at home. I will stay there again the next time I'm in town.

Cabin in West Stockbridge

5 out of 5 average rating, 7 reviews

Serene rustic mountain cabin in the Berkshires!

KellyRating, 5 stars4 weeks ago

Would love to come Back!

Flat in Richmond

5 out of 5 average rating, 21 reviews

Private Main Floor of Cottage on Richmond Pond

AlanRating, 5 stars6 months ago

Beautiful location overlooking the pond, conveniently located to towns and attractions, and private. Cozy, well stocked kitchen/cooking gear, everything you need as a contained retreat or a home base while exploring the Berkshires.

5 out of 5 average rating, 30 reviews

An Elegant Time Capsule in Downtown Lenox

CathieRating, 5 stars4 weeks ago

Carol has a beautiful house that is centrally located to great restaurants and local sites

Farm stay in Adams

5 out of 5 average rating, 4 reviews

Berkshires/Pet Friendly farm stay w/mountain views

SarahRating, 5 stars1 week ago

We had a great week full of hiking at Mt. Greylock and walking the local rail trail with our pups! Jessica’s place was a perfect touch down for everything we wanted to do. The camper felt private and cozy, a perfect place to relax and view beautiful scenery from the field. Getting to see the horses was a plus and our dogs loved hanging in the back yard. The camper was clean, comfortable and Jessica was very accommodating, making sure we had everything we needed! This is a place we would definitely come back to if we are in Adams again!