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Vacation rentals in Lenox

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Top-rated vacation rentals in Lenox

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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, 390 reviews

Restored 1735 Granary I King Bed + 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, 190 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

The exterior of the Gingerbread House Tower is shown, featuring unique architecture with a thatched roof and wooden siding. Lush gardens with vibrant flowers, including red blooms, surround the building, while green grass and trees enhance the natural setting.

Treehouse in Tyringham

4.99 out of 5 average rating, 308 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

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, 114 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!

A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.

Apartment in Stockbridge

4.96 out of 5 average rating, 111 reviews

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

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!

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

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 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!

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, 244 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, 128 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, 239 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, 180 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!

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Popular amenities for Lenox vacation rentals

Laptop-friendly workspace

Air conditioning

Lenox house rentals

A blue front door with an oval glass inset stands prominently against a white wooden facade. A small porch is visible, featuring a wooden bench and a gray chair. Fallen leaves are scattered across the gray decking.

Home in Richmond

4.96 out of 5 average rating, 27 reviews

Sunshine Cottage

Top guest favorite

A charming home is framed by tall trees and lush greenery, with a vibrant lawn in front. The white exterior features multiple windows, allowing natural light to brighten the interior. A clear blue sky with a few clouds completes the tranquil setting.

Home in Stockbridge

4.97 out of 5 average rating, 116 reviews

Greek Revival Farmhouse

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 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

Top guest favorite

An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.

Home in Stockbridge

4.95 out of 5 average rating, 139 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

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

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, 259 reviews

Cozy Vermont mini-house

Top guest favorite

A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.

Home in Stockbridge

4.89 out of 5 average rating, 102 reviews

Rabbit Run in the heart of Stockbridge Village

Other great vacation rentals in Lenox

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, 48 reviews

Cute, Cozy and Comfortable apartment

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 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.

4.93 out of 5 average rating, 40 reviews

Spacious 3 bedroom apt in Lenox historic downtown

A large, light blue Victorian house is set amidst a lush green yard, with a variety of trees and landscaped bushes. Outdoor seating is provided by adirondack chairs, and a red shed is visible in the background, all under a clear blue sky.

4.96 out of 5 average rating, 27 reviews

The Aviary

Top guest favorite

A charming Victorian house with a pointed roof is surrounded by vibrant foliage. Colorful flowers in shades of pink and green bloom in the foreground, adding life to the entrance. Clear blue skies are visible above, enhancing the inviting appearance of the property.

5 out of 5 average rating, 26 reviews

Sunny House in Downtown Lenox

The cabin is nestled in a wooded area, surrounded by lush greenery. A large deck extends from the front of the home, with firewood stacked neatly beside it. The architecture features an A-frame design, blending harmoniously with the natural landscape.

Chalet in Lenox

4.8 out of 5 average rating, 25 reviews

Spacious & Private Berkshires Chalet, in 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

A spacious living area features a comfortable gray sofa and a small black table. A green decorative vase and natural branches are placed beside a traditional stove on a brick hearth. A light rug covers the wooden floor, creating an inviting space.

Guest suite in Richmond

4.95 out of 5 average rating, 41 reviews

Berkshire Mountain Retreat

Quick stats about vacation rentals in Lenox

Total rentals
260 properties
Nightly prices starting at
R178 ZAR 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.
Do house rentals in Lenox have a gym?
Absolutely! We offer over 10 house rentals with a gym in Lenox. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Lenox?
Lenox has more than 80 family-friendly house 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 house rentals in Lenox?
Experience the best of Lenox with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Lenox have wifi?
Absolutely! We offer over 100 house rentals with wifi in Lenox. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Lenox have air conditioning?
Absolutely! We offer over 90 house rentals with air conditioning in Lenox. Enjoy a tailored experience with all the comforts you desire.
Are there Lenox hotel rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Lenox, available on Airbnb. Make a splash and soak up the sun in style!
What are the most popular amenities for House Rentals in Lenox?
Enhance your stay in our House Rentals with the most popular amenities: over 100 homes with wifi, over 10 homes with a gym, over 40 homes with a bbq area, over 90 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore