Vacation rentals in Lenox

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Quick stats about vacation rentals in Lenox

  • Total vacation rentals

    Explore 260 vacation rentals in Lenox

  • Nightly prices starting at

    Lenox vacation rentals start at $60 per night before taxes and fees

  • Verified guest reviews

    Over 8,500 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Lenox vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Lenox rentals

  • 4.8 Average rating

    Lenox stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Lenox

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

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Top guest favorite
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. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

ValueFamilyAmenities

4.95 out of 5 average rating, 325 reviews
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.
Home in Lee

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.

LocationValueLayout

4.98 out of 5 average rating, 256 reviews
Top guest favorite
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.
Home in Lenox

Home away from home: Minutes to Tanglewood.

Welcome to your home away from home! This charming 3-bedroom, 2.5-bathroom stylishly decorated home blends comfort and style in the Berkshires. It features a bedroom with a king, a bedroom with a queen, and one bedroom with a king and a twin over double bunk bed. Lots of couches and seating also. The kitchen has been refreshed with a table for 10. In the basement is a media room for movies and quiet time. We welcome you to our home and hope you enjoy your stay. Close to Tanglewood.

FamilyLocationCleanliness

4.94 out of 5 average rating, 64 reviews
Top guest favorite
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 relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

LocationFamilyBackyard

4.99 out of 5 average rating, 328 reviews
Superhost
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

Cozy Chalet Near Downtown Lenox, Foliage Beauty

Wonderful Views in a Private, Modern Setting Light-filled modern chalet next to Kennedy Park with beautiful views, a spacious living room, and a peaceful garden for morning coffee, evening wine or yoga. Designed for families and friends, with a private upstairs main suite plus comfortable guest rooms. Minutes to downtown Lenox, hiking trails, lakes, great dining, and the best of the Berkshires. Perfect for a fall getaway filled with hikes, nature, and cozy times. Healthy fun!

FamilyValueDecor

4.87 out of 5 average rating, 46 reviews
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

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.

FamilyValueAir conditioning

4.99 out of 5 average rating, 343 reviews
Top guest favorite
Home in Pittsfield

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis. 

FamilyLocationSkiing

5.0 out of 5 average rating, 43 reviews
Guest favorite
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

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.

LocationFamilyParks

4.95 out of 5 average rating, 155 reviews
Guest favorite
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.
Apartment 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.

LocationFamilyQuiet

4.96 out of 5 average rating, 119 reviews
Top guest favorite
A charming green cottage is surrounded by autumn foliage, featuring a welcoming front porch with white railings. Large windows provide ample natural light, while the overall structure showcases a traditional design with a gabled roof and balcony, nestled in a serene outdoor setting.
Home in Lee

GreenHouse

Relax and enjoy the Berkshires at this peaceful place to stay in the beautiful Berkshires of western Massachusetts. GreenHouse is the guest cottage for the historic Hyde House which is on the National Register of Historic Places. Located within walking distance of Lee, Ma, the house is also conveniently located near Stockbridge and Lenox.

FamilyValueNearby

4.99 out of 5 average rating, 144 reviews
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.
Home in Lenox

Sunny House in Downtown Lenox

This gem is perfectly situated on a quiet residential street in historic downtown Lenox. Take a short 3 minute walk to the restaurants, shops, and galleries of the village of Lenox, or drive a few minutes to Tanglewood, Shakespeare & Co, Kripalu, and Kennedy Park, as well as local ski areas and all the Berkshires has to offer.

ValueLocationDecor

4.97 out of 5 average rating, 39 reviews
Top guest favorite
Home in Lenox

The Berkshire Quintessential Cape downtown Lenox

Experience the Best of the Berkshires in the Heart of Lenox Welcome to this charming, in-town Lenox retreat—where classic Berkshire character meets thoughtful design. Bathed in natural light, the home features stunning oak floors, crisp white walls and an abundance of windows that create a bright, airy atmosphere throughout.

LocationFamilyBathroom

5.0 out of 5 average rating, 13 reviews

Popular amenities for Lenox vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Lenox's top sights

Mount Edith Wharton's Home

260 locals recommend

Kripalu Center for Yoga & Health

170 locals recommend

Bousquet Mountain Ski Area

177 locals recommend

Shakespeare & Company

168 locals recommend

Tanglewood

122 locals recommend

Balderdash Cellars

94 locals recommend

Other great vacation rentals in Lenox

Guest favorite
Apartment in Lenox

The Penthouse, Downtown Lenox by Evergreen Home

FamilyValueGetting around

4.91 out of 5 average rating, 91 reviews
Guest favorite
Home in Lenox

Historic Haven at 93 Church St.

FamilyLocationLayout

5.0 out of 5 average rating, 11 reviews
Guest favorite
A bright living room features a comfortable white sofa and a plush armchair beside a coffee table on a patterned rug. Large windows allow natural light to illuminate the space, while a television is positioned against a wooden accent wall. A potted plant adds a touch of greenery.
Home in Lee

Spacious Central Berkshires Home for Groups

LocationFamilySleep quality

4.9 out of 5 average rating, 60 reviews
Top guest favorite
Home in Lenox

Charming Cottage in Downtown Lenox

LocationFamilyAccuracy

4.97 out of 5 average rating, 33 reviews
Top guest favorite
The guesthouse is set amidst lush greenery, featuring a stone wall bordering a gravel driveway. A sloped roof and gabled entrance harmonize with the surrounding trees, creating a private and inviting atmosphere. Natural light highlights the exterior's subtle tones.
Guesthouse in Lenox

Guest House at Stonover Estate

LocationSleep qualityLong stay

5.0 out of 5 average rating, 69 reviews
Guest favorite
An inviting kitchen features a central island with barstools and warm wood accents. Large windows allow natural light to fill the space, highlighting the modern appliances and tasteful decor. A dining area with additional seating is visible in the background, promoting a sense of openness.
Home in Lenox

Spacious Lenox Farmhouse | Retreat Near Tanglewood

FamilyLocationLayout

4.85 out of 5 average rating, 26 reviews
Top guest favorite
Home in Lenox

7 Minute Walk to Tanglewood from New 2BR Home

LocationValueAccuracy

5.0 out of 5 average rating, 12 reviews
Top guest favorite
The exterior of the cottage features light grey siding and a charming front door adorned with seasonal wreaths. Large windows invite natural light, while the surrounding snow-covered landscape highlights the tranquility of the setting. A garage is visible on the side of the property.
Home in Lenox

The Lenox Cottage

LocationFamilyCondition

4.95 out of 5 average rating, 22 reviews

When is the best time to visit Lenox?

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Avg. price$286$300$267$273$283$304$304$300$261$288$266$302
Avg. temp23°F25°F33°F46°F56°F64°F69°F67°F60°F49°F39°F29°F

Frequently Asked Questions

  • What are the best places to stay in Lenox?

    Stay near the town center to enjoy walkable access to shops, cafes, and cultural venues, or choose accommodations nestled in the wooded outskirts for a peaceful retreat. Vacation rentals frequently feature historic charm and modern amenities.

  • What are the best things to do in Lenox with kids?

    Family-friendly activities include visiting Pleasant Valley Wildlife Sanctuary for nature walks, exploring creative workshops at local arts centers, and enjoying interactive exhibits at nearby museums. Many parks around Lenox have open spaces for play.

  • What are some of the best things to do in Lenox?

    Explore the grounds and exhibits at The Mount, wander art galleries around the town center, or attend performances at Tanglewood. Lenox has scenic parks, boutique shops, and locally rooted dining experiences.

  • How is the weather in Lenox?

    Lenox experiences cold winters, with temperatures often between 13–32°F (-11–0°C), and warm summers reaching 57–81°F (14–27°C). Spring and fall bring milder temperatures, frequent rainfall, and vibrant seasonal landscapes.

  • When is the best time to visit Lenox?

    Late spring through early fall is frequently suggested for mild weather, outdoor concerts, and lush landscapes. Autumn brings colorful foliage, while winter holds opportunities for snow activities in the Berkshires.

  • What are the best places to visit in Lenox?

    The Mount offers literary history and gardens, while Tanglewood attracts music enthusiasts during its performance season. Main Street has locally rooted shops, and area parks provide natural beauty for visitors year-round.

  • What are some hiking trails in Lenox?

    Kennedy Park is often recommended for its gentle trails through forested landscapes. Pleasant Valley Wildlife Sanctuary has wooded paths, boardwalks, and opportunities to spot local wildlife along the way.

  • What are some family activities we can do in Lenox?

    Explore scenic hiking spots, attend seasonal outdoor concerts, or join nature programs at wildlife sanctuaries. Lenox’s green spaces and museums accommodate a variety of interests for all ages.

  • What are some of the best day trip ideas from Lenox?

    Venture to nearby towns known for their art museums, historic estates, or hiking areas, or explore scenic spots in the Berkshires for mountain views and outdoor activities. Regional gardens and nature preserves are often recommended for varied experiences.

  • Are there any pet friendly accommodations available in Lenox?

    Lenox has pet-friendly vacation rentals across both central and wooded areas. Several local parks and trails, including Kennedy Park, make it easy to get outside with your dog.

  • What are some local tips for visiting Lenox?

    Locals suggest exploring early in the day for a quieter experience at parks and museums, and checking the calendar for seasonal events or live performances. Many shops and venues have locally crafted goods and rotating exhibits.

  • What is Lenox known for?

    Lenox is known for its lively arts scene, historic sites, and access to natural spaces in the Berkshires. The town draws visitors for music, culture, and outdoor recreation throughout the year.

  • What are the best hidden gems to explore in Lenox?

    Discover tranquil nature spots like Kennedy Park, or explore quieter art spaces and local bookshops around Main Street. Small cafes and tucked-away galleries bring a welcoming atmosphere for slower exploration.

  • What are the best foods to try in Lenox?

    Frequent favorites include locally sourced farm-to-table dishes, New England seafood options, and artisanal baked goods. Lenox has welcoming cafes and restaurants that highlight regional flavors and seasonal ingredients.

  • What should I bring for a trip to Lenox?

    Pack layers for changing temperatures, sturdy shoes for exploring trails, and an umbrella or rain jacket, especially in the wetter summer and fall months. In winter, warm outerwear and snow-friendly boots are helpful for outdoor activities.

  • What is the nightlife in Lenox like?

    Lenox has a relaxed nightlife with cozy taverns, live music performances, and casual wine bars clustered around the town center. Seasonal concerts and artistic events create a lively atmosphere during summer and festival months.

  • What are the most popular events or festivals in Lenox?

    Tanglewood is known for its summer music festival, drawing audiences during warm months. Lenox also has arts festivals and outdoor concerts, especially around late spring and early fall.

  • Are there family friendly vacation rentals in Lenox?

    Family-friendly vacation rentals are available throughout the town center and surrounding areas, often featuring spacious layouts and equipped kitchens. Many options are close to parks or cultural sites, making outings convenient.

Destinations to explore