Vacation rentals in Lenox

4.94 out of 5 average rating, 141 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

4.9 out of 5 average rating, 272 reviews

A detached red barn is surrounded by a grassy yard, with patches of snow visible on the ground. The property features a gravel driveway leading to the barn's double garage doors. Mature trees line the background, offering a natural setting.

Guesthouse in Lenox

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Cottage in Great Barrington

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

4.93 out of 5 average rating, 308 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.

Lush, colorful flowers surround the entrance of the cottage, adding a vibrant touch to the exterior. A combination of greenery and blooms creates a welcoming atmosphere. The cottage features large windows, allowing for ample natural light and offering views of the blooming landscape.

4.92 out of 5 average rating, 237 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!

An open living and dining area is showcased with a light wood floor and large windows. A teal sofa, accented with bright cushions, faces a coffee table on a patterned rug. A dining area with modern chairs is visible in the background, enhancing the welcoming layout.

4.93 out of 5 average rating, 237 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!

4.98 out of 5 average rating, 257 reviews

A spacious bedroom features a large queen bed with a white duvet and decorative pillows. Two sets of French doors open to an outdoor view, flanked by soft curtains. A cozy seating area with a light-colored sofa adds comfort, illuminated by natural light from the windows.

Guest suite in Valatie

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

4.99 out of 5 average rating, 289 reviews

A spacious kitchen is complemented by large windows that allow natural light to fill the area. An island with a countertop of mixed materials serves as a central gathering spot. A colorful rug lies on the concrete floor, while various kitchenware is neatly arranged on shelves.

Home in Lee

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

A sunlit living area is furnished with a spacious sectional sofa and a round coffee table atop a patterned area rug. The hardwood floors and natural light from the multiple windows enhance the room's inviting feel, complemented by a decorative fireplace and wall art.

4.87 out of 5 average rating, 162 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, 259 reviews

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

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, 292 reviews

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

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)

Guesthouse in Stockbridge

A modern kitchenette is visible, featuring black cabinetry and open shelving with dishware. A dining area with a table and four chairs is situated nearby, while light streams in through a skylight and window, illuminating the open space.

4.96 out of 5 average rating, 247 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.

4.88 out of 5 average rating, 196 reviews

An inviting entrance area showcases a vintage Coca-Cola vending machine. A wooden door leads into a room with a detailed patterned wallpaper. A decorative stove stands prominently, complementing the warm aesthetic of the space.

Apartment in Lenox

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Lenox vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Lenox house rentals

4.93 out of 5 average rating, 105 reviews

Home in Pittsfield

Net Zero home with rustic Berkshire charm

4.98 out of 5 average rating, 121 reviews

A welcoming front porch features several seating options, including a rocking chair and cushioned chairs. The porch is decorated with area rugs and has a ceiling fan for comfort. Lush greenery and a shared backyard are visible in the background, enhancing the outdoor space.

Home in Pittsfield

Charming Gem in Heart of the Berkshires

4.97 out of 5 average rating, 219 reviews

A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.

Home in Lee

Berkshire 4 season home

4.99 out of 5 average rating, 130 reviews

A charming two-story home is set on a landscaped plot with a gravel driveway. A wooden staircase leads to the entry, flanked by vibrant flower beds. The natural backdrop features lush trees and a striking granite ledge, creating a peaceful and inviting outdoor environment.

Home in Great Barrington

Granite Ledge, Modern home in a unique setting

Superhost

A charming ranch-style home is surrounded by vibrant autumn foliage. The exterior features wooden siding and large windows, providing natural light. A stone pathway leads to the entrance, and a well-maintained yard showcases a variety of mature trees and shrubs, creating a peaceful retreat.

4.86 out of 5 average rating, 361 reviews

Lenox, MA Getaway, Mile to town!

4.97 out of 5 average rating, 264 reviews

Home in Pownal

Cozy Vermont mini-house

4.89 out of 5 average rating, 148 reviews

The exterior of a charming yellow house is showcased, featuring red doors and large windows. Lush greenery surrounds the entrance, with vibrant flowers in varying shades of white and purple in the foreground. An American flag is affixed to the house, adding a touch of patriotism.

Home in Dalton

The Yellow House

4.99 out of 5 average rating, 373 reviews

Home in New Lebanon

The old sawmill from 1771

Other great vacation rentals in Lenox

A spacious living room features a cozy sectional couch alongside a wooden coffee table. Two armchairs are placed next to a floor lamp, and natural light streams through two large windows adorned with sheer white curtains. A soft area rug complements the hardwood floors.

5 out of 5 average rating, 25 reviews

Cliffwood Cottage

4.97 out of 5 average rating, 58 reviews

A serene sleeping area features a spacious bed adorned with white linens and a decorative pillow displaying floral patterns. An orange lamp softly illuminates the room, contrasting with the muted gray walls. A framed piece of art adds a touch of sophistication above the bed.

Apartment in Lenox Dale

Cute, Cozy and Comfortable apartment

4.93 out of 5 average rating, 85 reviews

A scenic landscape unfolds with rolling hills adorned in vibrant autumn foliage. The rich hues of orange, red, and yellow contrast with a tranquil water body in the distance, set against a cloudy sky that hints at the changing seasons.

Apartment in Lenox

Lenox Ma.

4.99 out of 5 average rating, 68 reviews

A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.

Apartment in Stockbridge

Stockbridge private apartment

Guesthouse in Lanesborough

5 out of 5 average rating, 9 reviews

The Carriage House: Spotless, Charming 2 Bedroom

Superhost

A bright, serene bedroom features a spacious bed with a light textured blanket. Two wooden nightstands with lamps are positioned on either side. Natural light filters through multiple windows, illuminating the warm oak floors and clean, minimalist aesthetic.

Apartment in Lenox

4.9 out of 5 average rating, 70 reviews

The Penthouse, Downtown Lenox by Evergreen Home

5 out of 5 average rating, 15 reviews

The exterior of a cozy cottage showcases a spacious wooden deck with seating options, including a table and chairs. A grill is positioned nearby. Lush green grass surrounds the home, complemented by a clear sky with scattered clouds.

Cottage in Pittsfield

The Sunset House

A spacious kitchen area is presented with light-colored cabinetry and a modern countertop. A wooden table, designed to accommodate ten, is centered in the room. Open shelves display glassware, and stainless steel appliances are visible, enhancing the functional layout.