Holiday rentals in Lenox

5 out of 5 average rating, 31 reviews

A welcoming bedroom features a spacious bed dressed in white linens and accented by two bedside tables with lamps. Natural light fills the room through a large window, complemented by a decorative rug with floral patterns on the floor.

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, 158 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.

4.91 out of 5 average rating, 122 reviews

A modern bedroom showcases a spacious bed with crisp white linens. Accent lighting frames the walls, and a patterned area rug adds warmth to the space. A compact seating area with stylish benches complements the décor, while an entrance leads to a private bathroom.

Flat in Great Barrington

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

4.93 out of 5 average rating, 241 reviews

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.

Home in Lenox

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!

Guest house in Housatonic

A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.

4.96 out of 5 average rating, 156 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.

A comfortable living area features a gray futon sofa and a wooden coffee table. Natural light enters through two large windows, which are equipped with shades. A compact television is positioned on a stand in the corner, complementing the modern decor.

4.92 out of 5 average rating, 51 reviews

Comfortable Pittsfield Loft

Located in the center of the Berkshires, this newly renovated Pittsfield apartment is comfortable and convenient. Come enjoy the new kitchen and delightful walk in shower. Centrally located to all of the wonderful Berkshires attractions this one bedroom apartment offers new appliances, driveway parking, washer and dryer. Yuhong and Mike live on-site in the apartment below and they are dedicated to providing an excellent guest experience. THIS IS A NO SMOKING APARTMENT

4.99 out of 5 average rating, 306 reviews

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.

4.95 out of 5 average rating, 278 reviews

An open floor plan reveals a spacious apartment with yoga slings hanging from the ceiling. A vintage red love seat is situated in a reading loft, while a kitchen area is visible towards the back. The flooring features an eclectic mix of textures and colors.

Loft in Troy

Large bohemian loft: The Chromium Compound

Large storefront converted to colorful open plan apartment in the heart of downtown Troy. Blocks away from RPI, and steps away from most of Troy's nightlife. Warning: this urban bohemian experience may bring back memories of Williamsburg Brooklyn or Downtown LA in the 90's. Note that sounds from outside and adjacent apartments may bother light sleepers, so don't book this one if that is a concern for you. Also parties are not allowed because of close neighbors! Thanks!

Superhost

A spacious living area features light-colored walls and wooden flooring. A gray sectional sofa is positioned beside two white armchairs, with accent pillows enhancing comfort. A coffee table sits at the center, surrounded by a vibrant area rug. Natural light is provided by windows with simple treatments.

Guest suite in Lee

4.76 out of 5 average rating, 145 reviews

Cozy Guesthouse Near Downtown, Lee

Welcome and enjoy our renovated Guesthouse at Lee, MA, staying on main street (15 minutes from Great Barrington and 20 minutes from Pittsfield). It is also 3 mins to Outlet and 19 mins to the closest Ski area.The master bedroom has a queen size soft mattress, and the second bedroom has a queen bed also. The kitchen has a brand new refrigerator, a gas range, and units for cooking. You will enjoy the comfortable stay! Owners live upstairs and be friendly to all visits.

4.99 out of 5 average rating, 284 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.

4.96 out of 5 average rating, 124 reviews

The living area features a comfortable seating arrangement with a patterned armchair and a light-colored sofa accented by a vibrant throw. A side table is positioned next to the sofa, and a wall clock adds a decorative touch, while wooden flooring enhances the cozy ambiance.

Flat in Troy

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

4.97 out of 5 average rating, 103 reviews

A light and neutral living room showcases a comfortable sectional sofa with decorative pillows. A round marble coffee table is positioned in front, adorned with a small plant. Two framed art pieces hang above the sofa, and textured rugs lie across the wooden flooring.

Flat in Lenox

Historical Downtown 1 Bedroom Apartment

Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen 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.

Popular amenities for Lenox holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Lenox

5 out of 5 average rating, 31 reviews

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.

Home in Lenox

Cliffwood Cottage

A spacious studio is furnished with a large bed covered in a blue and white striped blanket. Two windows provide natural light, and a small seating area is visible. A solid door leads outside, with a bar-height table and stools located near the entrance.

4.54 out of 5 average rating, 52 reviews

Beautiful Blue Studio downtown

4.87 out of 5 average rating, 167 reviews

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.

Home in Lenox

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

A compact sleeping area features a gray upholstered bed with white bedding and two pillows. A modern lamp illuminates the space, highlighting a nightstand beside the bed. A doorway leads to an adjacent area, with slippers visible on the floor.

4.69 out of 5 average rating, 86 reviews

Newly Renovated, and Spacious great for family

Guest house in Stockbridge

The exterior of the wooden cottage is showcased, featuring a large gray facade with three prominent windows. A deck extends from the front, complemented by outdoor seating and a patio umbrella. Lush greenery surrounds the property, enhancing its rustic charm.

4.93 out of 5 average rating, 44 reviews

Light-filled Carpenter's Cottage w/ EV charger!

Hotel room in Pittsfield

4.5 out of 5 average rating, 8 reviews

1 BD • Berkshires Apartment • Full Kitchen/Pool

4.94 out of 5 average rating, 85 reviews

The exterior showcases a spacious modern guesthouse surrounded by carefully maintained landscaping. A winding driveway leads to the entrance, with ample green space, trees, and a clear blue sky overhead. The design features a blend of classic and contemporary architectural elements.

Guest house in Lee

Berkshires Zen | Mountain Views & Private Porch

A cozy living area features two wooden chairs with soft cushions and a decorative throw. A vibrant area rug adds color to the space, while a lamp provides gentle lighting. An open doorway leads to a bedroom, with natural light filtering through the window.