We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Lenox

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Lenox

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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

4.93 out of 5 average rating, 387 reviews

Restored 1735 Granary I Mountain Views + Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 20-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.

Guest suite in Richmond

4.93 out of 5 average rating, 189 reviews

Tanglewood/Private Ranch/Kid&Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

Top guest favorite

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.

Apartment in Lenox

5 out of 5 average rating, 25 reviews

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!

Top guest favorite

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.

4.97 out of 5 average rating, 215 reviews

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Top guest favorite

A cozy sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.

Guesthouse in Cummington

5 out of 5 average rating, 109 reviews

Clark Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

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.

4.93 out of 5 average rating, 234 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!

A spacious living area features a stone fireplace as a focal point, complemented by wooden beams on the ceiling. Comfortable seating is arranged around a central coffee table, creating an inviting atmosphere. A television is mounted above the fireplace, and glimpses of the kitchen and bedrooms are visible in the background.

Home in Stockbridge

5 out of 5 average rating, 3 reviews

Summer Cottage at The Lake!

Welcome to our funky little summer cottage! Tucked in a stone's throw from the Stockbridge Bowl and just down the street from Tanglewood, this home offers convenient access to fun in The Berkshires. Whether you’re at the lake, Tanglewood, or relaxing on the porch, there's something for everyone. Bright, modern, and charming, it's the ideal spot to make memories with loved ones.! Enjoy the best that The Berkshires have to offer at this peaceful and centrally-located cottage.

Top guest favorite

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.

4.99 out of 5 average rating, 287 reviews

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.

Top guest favorite

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

4.99 out of 5 average rating, 237 reviews

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.

The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.

Apartment in Lenox

4.96 out of 5 average rating, 126 reviews

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

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.

Guesthouse in Stockbridge

4.95 out of 5 average rating, 238 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.

A cottage entrance is framed by lush greenery, with a stone pathway guiding guests to a welcoming front porch. The wooden door features a round window, and large windows on either side allow natural light to illuminate the space, surrounded by vibrant flora.

4.96 out of 5 average rating, 179 reviews

Lenox - Walk to Town - Berkshire Home

Come, enjoy the Berkshires! This cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a large front yard and beautiful backyard for grilling. Explore the best of Lenox and the Berkshires activities and fare! Sitting in this cottage surrounded by forest, you really feel like you are in the shire!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Lenox vacation rentals

Laptop-friendly workspace

Air conditioning

Lenox house rentals

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

An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.

Home in Pittsfield

4.93 out of 5 average rating, 102 reviews

Net Zero home with rustic Berkshire charm

Top guest favorite

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

Home in Great Barrington

4.99 out of 5 average rating, 100 reviews

Private Home in The Berkshires (New Hot Tub!)

Top guest favorite

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

4.99 out of 5 average rating, 125 reviews

Granite Ledge, Modern home in a unique setting

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, 359 reviews

Lenox, MA Getaway, Mile to town!

An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.

4.97 out of 5 average rating, 257 reviews

Cozy Vermont mini-house

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, 236 reviews

The Berkshire Quintessential Cape downtown Lenox

Top guest favorite

A warm fire burns within a stone fire pit, with flames flickering against the evening sky. The serene lake reflects the fading light, while a wooden dock is visible in the distance, surrounded by tall reeds and lush greenery.

5 out of 5 average rating, 28 reviews

Lakefront Retreat -Private Dock,creek,and Fire pit

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

A spacious living room is presented, featuring a large, dark sectional couch with various cushions. A 60-inch 4K TV is positioned on a low media console, opposite the couch. Natural light filters through sheer curtains into the room, complemented by a soft area rug and a potted plant.

4.88 out of 5 average rating, 49 reviews

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

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

4.96 out of 5 average rating, 46 reviews

Cute, Cozy and Comfortable apartment

Top guest favorite

A view from the deck showcases the surrounding landscape, including trees with varied foliage and distant mountains under a clear blue sky. The roof of the adjacent building is visible in the foreground amid the garden area.

Guesthouse in Pittsfield

4.97 out of 5 average rating, 87 reviews

The Nest at Birdland

A view from the loft captures the open concept living space below. Natural light filters through multiple windows, highlighting a dining area with a wooden table and chairs. Decorative plants and cozy seating create an inviting atmosphere, complemented by wooden flooring and accent walls.

Cottage in Lenox

4.96 out of 5 average rating, 68 reviews

The Jaynes House ~ Cozy Lenox Retreat

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.

Apartment in Pittsfield

4.83 out of 5 average rating, 52 reviews

Newly Renovated, and Spacious great for family

A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.

4.92 out of 5 average rating, 38 reviews

Spacious 3 bedroom apt in Lenox historic downtown

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.

Guesthouse in Stockbridge

4.94 out of 5 average rating, 34 reviews

Light-filled Carpenter's Cottage in Stockbridge

Quick stats about vacation rentals in Lenox

Total rentals
260 properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
8K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
40 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Lenox?
Four-legged friends are welcome in Lenox. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Lenox?
Yes! Work meets play with ease at over 130 vacation rentals in Lenox featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Lenox vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Lenox, available on Airbnb. Make a splash and soak up the sun in style!
Do hotel rentals in Lenox have a gym?
Absolutely! We offer over 10 hotel rentals with a gym in Lenox. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Lenox?
Lenox has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Lenox have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Lenox. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Lenox?
Experience the best of Lenox with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Lenox have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Lenox. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Lenox have air conditioning?
Absolutely! We offer over 20 bed and breakfast rentals with air conditioning in Lenox. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Bed And Breakfast Rentals in Lenox?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore