Vacation Rentals By Owner In Lenox, MA

HYDRANGEA HILL - It doesn't get much better than this for style and proximity. Hydrangea Hill (circa, 1898) is located on a quiet street less than a half-mile walking distance to downtown Lenox, and only two miles to Tanglewood's main entrance. The yard offers a garden atmosphere with a lightly wooded wetland area on the back and side. You'll recognize it immediately by the white picket fence curving around the front as the brick walkway leads you to the front door. The house features three bedrooms, each with quality linens and mattresses; one with twin beds, one with a queen bed, and a master suite with a king bed. You'll love the master bathroom, which features a Carrara marble top, double vanity, and large walk-in glass and tile shower with a spa bench. Without a doubt, the best feature in the house is the large open living space and fully equipped modern kitchen with all you need for a family gathering or for cooking an intimate gourmet meal. The farmhouse style table is 10 feet long and easily seats ten-twelve individuals. For movies at home or sports followers, you'll love the Samsung 65” Crystal Ultra High Definition TV and of course, WiFi throughout the house. On chilly winter nights, get cozy in front of an electric fireplace that offers both heat and ambiance. Other amenities include, a guest bath upstairs near bedrooms, a half bath on the main floor with laundry facilities, and an enlarged paved patio with (weather permitting) comfortable wicker outdoor seating, propane fire pit, and propane grill. You'll love the Berkshires and all that Hydrangea Hill has to offer.brIf Hydrangea Hill had a motto, it would be Veni, Relaxant, Fruere, Latin for Come, Relax, Enjoybr** Located nearby, The Mount, the historic home of author Edith Wharton, was mentioned in USA Today’s Ten Best Readers’ Choice travel awards for holiday historic home tours! brbrI invite you to immerse yourself in a Berkshire winter wonderland like no other. Picture cozy nights inside with an electric fireplace, outside snow-covered trails perfect for skiing, and the enchanting glow of holiday lights against the crisp night air. Whether you’re a thrill-seeker or prefer a more tranquil winter experience, Lenox has it all. Explore miles of pristine downhill slopes at nearby ski resorts or enjoy peaceful cross-country skiing through the scenic trails that wind through Kennedy Park, only minutes away from Hydrangea Hill. With something for every type of winter traveler, Lenox is the ultimate destination for a cozy winter getaway. Embrace the timeless beauty and historic charm of Lenox — a serene winter escape that promises unforgettable moments. brbrPlease Note: If I’m not in residence, JULY & AUGUST EACH HAVE A 31 NIGHT MINIMUM STAY. Additionally, in event of a any cancellation that results in a 50% or 0% refund, and another guest rents for any or all of the same time frame, at my discretion, I will try to reimburse any duplicate monies already received.]

5 STAR CASUAL ELEGANCE for 5 STAR GUESTS

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$1366.73

Our Designer Farmhouse has been lovingly updated and impressively furnished with careful thought and no expense spared. The home is spacious enough to host the whole family while still providing room to wind down, evoking a haven of relaxation. Many recent updates, upscale furnishings and curated touches make this home feel sophisticated and welcoming.brThe Location:br Located 1 mile to downtown Lenox and 2.5 miles to Tanglewood, you'll enjoy the quiet privacy but still be close to popular local attractions, shopping and dining . Just minutes to the newly updated Bousquet Ski Mountain for Ski and Summer Concerts, 3 miles to Guidos Fresh Marketplace, Big Y, Price Chopper, and CVS as well as Lenox’s beloved Spa Resorts Canyon Ranch and Miraval. Lenox is centrally located and convenient for travel if you plan to visit other popular Berkshire towns and attractions in North or South County.brbrIf you’re coming to enjoy outdoor recreation in the area we are located just across Rt. 7 from Kennedy Park 15 miles of town-maintained trails for hiking, trail running and cross country skiing. Stockbridge Bowl is just a 5 minute drive for boating, kayaking, and paddle boarding.brThe House:brDrive down the long pebble driveway to a quiet and serene setting. Enter into a large open foyer with huge picture windows over looking the forest and gardens. If you like to cook you will love the newly updated and fully stocked chefs kitchen ; 6 burner gas stove with griddle and double ovens, sizable island with counter seating and plenty of space for cooking meals. The large corner banquette seats up to 10 comfortably. In the warmer months the outdoor grill on the patio is perfect for grilling dinner to enjoy outside or in. brEnjoy the outdoors under the cedar pergola on the stone patio with comfortable lounge furniture and fire pit surrounded by perennial gardens and woodland views. The glass enclosed 3 season porch and the open front porch overlooking the flower beds are other favorite places to relax and listen to the birds, both furnished comfortably for a relaxing visit. brEvery room in the house has windows over looking the wooded surroundings and beautiful landscaping, bringing in plenty of natural light and giving a sense of serenity and privacy. The house is set back from the road and far enough from neighbors that you can enjoy peace and quiet when in or outside.brOpen to the kitchen is an impressive formal living room with wood burning fireplace to stay cozy in the winter and access to outdoor patio for easy summer entertaining. A large pantry/ laundry room is off the kitchen, and a large closet in the foyer is perfect for storing luggage coats and shoes. Half bath located off the foyer. br The office is spacious with glassed French doors for privacy, WIFI booster, printer, wireless charger for your phone and large writing desk for your laptop. The first floor is equipped with built in speakers to enjoy your music (Sonos system installed, just download the app on your smart phone!). Eero wi-fi boosters guarantee fast connection for multiple users.brbrA separate Den/TV room off of the foyer completes the first floor with large flat screen Smart TV and cozy couch with chaise for movie watching. A table for 2 by the window provides a nice place of coffee or a board game.brbrThe 2nd floor has 4 Bedrooms, including a Large Primary Suite (500 sq of privacy) and 3 full bathrooms. brThe spacious Primary Suite includes a King Bed, Sitting area, Large flat screen with apple TV and cable channels, Large Dressing room, full bath with double sinks, soaking-tub and large marble shower. brTwo of the guest bedrooms in 1 wing share a large newly renovated full bath with marble tile, large vanity with double sinks and large shower. Guest Room 1 has Double Bed, large closet and a dresser. Guest Room 2 has a Queen Bed, 2 large closets, drawers, and TV.brGuest Bedroom 3 down the hall has a King sized Tempur-pedic bed and flat screen TV and its own bathroom with tiled shower, venetian plaster walls and sink/vanity. brbrWe provide a guest book full of our top-rated hikes, restaurants, shopping and spas in the area complete with directions and descriptions to enhance your stay. An assortment of local goods are offered as a Welcome upon your arrival.brbrSimply put, this property is an elevated renting experience. Each year we make several adjustments and upgrades to our property catered to providing an exceptional stay for our guests. Just read all of our wonderful reviews ...we are committed to giving you a 5 Star stay! brbrVisit our other nearby VRBO rental- A chic + cozy fully renovated and beautifully furnished 1 bd/1ba cottage : #2964171

Chic Modern Farmhouse 1 Mile to Downtown Lenox

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$1229.45

A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxury whilst offering close proximity to Tanglewood, Ski slopes, hiking trails, Lakes, the historic town of Lenox and other Berkshire towns. This listing is for the Main House that accommodates a maximum of 11 (you can also rent this property in a larger format - Main House + the Studio - which accommodates 15. VRBO ID. 1266558). brbrMain House [4400sqft]: This charming 1920s log cabin has an expansive layout with a breezeway connecting a newer section. Inside you will find five well-appointed bedrooms, three full bathrooms and a powder room. The heart and soul of the house is an expansive living room with a brick fireplace, big comfortable sofas, a TV area, and a grand piano. Step out of the living room, onto a balcony to take in the pristine views of the valley below. Right behind the living room is a study and a king bedroom with a full bath. The second floor has two spacious bedrooms (one king and three twins respectively) which share a full bath with a claw foot tub and a separate shower. At the other end of the house, you will find an inviting country kitchen that opens up to a large dining area. The farm table seats 10 comfortably, and there is an adjoining dining area for children. Above the kitchen are two queen bedrooms, a hall bathroom with shower, and a TV den. brbrGazebo: We have built a fantastic screened-in living space by the woods' edge, with a 16 seat dining table and sofas for lounging. In this substantial new space you will be able to enjoy long, leisurely meals al fresco, and then curl up for a nap while listening to birds and crickets sing. During the cold season, you can enjoy a fire in the large in-ground fire pit right outside the Gazebo.brbrNot just a conventional vacation rental, we’ve set up this property as our own retreat with a lot of thought and care. Choosing to rent a home instead of booking a hotel room allows you the space to get together with friends and family in comfort and privacy. But you shouldn't have to sacrifice the luxury you may enjoy during a hotel stay. At the end of your stay, all you need to do is pack your bags and walk out the door. We don't expect you to strip the beds, empty the fridge, or take out the garbage. We offer a worry-free experience right up to the last moment!brbr** BEFORE YOU INQUIRE**brThank you for understanding that we have no flexibility on these points:br- We require a 3 night minimum during July and August.br- This house is pet free, there are absolutely NO exceptions to the pet policy. Even if your companion is small, well behaved or hypoallergenic.

Luxury Berkshires Retreat in Lenox - Main House

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$671.6

Located on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a Smart 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.brLocated on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a Smart 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.

Apartment

Farmhouse-Loft -48 Main Street, Lenox, MA

Lenox, Massachusetts, United States

2

Bed

2

Bath

6

Sleeps

$1107.7

Fully renovated and decor updated in 2024! 8 acre property, shared with one carriage house not rented, with amazing views of October Mountain and one mile from Lenox Center. 1.5 miles from Tanglewood. The property features so much, pool, chess set, sport court, gardens abound, a wraparound porch you can enjoy a relaxing day. A wonderful place to re-charge and enjoy your time. The property has 5 bedrooms and a separate crib room. It sleeps 10 in beds (without the child in the crib room) - a maximum of 16 are allowed in the house.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$510.2

Location, Location, Locationbr4 BR, 3½ bath immaculate property in Lenox available as a short-term rental. A ten minute walk from downtown Lenox Center, and 5 minute drive from Tanglewood (on a quiet evening you often hear music from the back porch). All the cultural attractions of the Berkshires within a short drive. A beautiful, comfortable, fully furnished, and tastefully decorated home, with entry hallway, full kitchen, dining room, living room, screened-in porch, deck, and large backyard. Very quiet, and sunny, with two primary bedroom suites (one on first floor) plus two additional bedrooms. Ideal for a perfect vacation for one or two couples or a family. You will be delighted with all this home has to offer.brbrFor the security of our guests, and the safety of our home, there is an external video camera installed at the front entrance. The camera looks at the driveway and the front steps only.

Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$690.31

Modern, bright and renovated. Mid Century vogue furnishings, hardwood floors and central A/C are just some features you will find. Our lovely 3 Bedroom 2 full bath home is located on a quiet dead end street and a short distance into downtown. The Tanglewood Main gate is less than a mile away. Large deck with seasonal lounge and dining furniture overlooking backyard. Enjoy all that Lenox has to offer in this pristine location.brBroker owned.

NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$1739.33

Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the beautiful southeast view over Tanglewood and Lenox. The deck and screened porch, off the gourmet kitchen, offer dining al fresco and panoramic mountain views of sunset and sunrise. A very unique home based in the classics with 4500 sq ft of easy living on almost 2 acres. brbrSituated minutes from Downtown Lenox, this country chic home is great for entertaining friends and family, while offering a calm, secluded and romantic setting upon a hill. All bedrooms are en suite for an elegant Berkshires weekend and longterm vacation getaway, year-round. Large interior doors and huge exterior windows create a loft-like feeling in every room.brbrbrThe bold design is balanced with traditional shingle style elements and reminiscient of the famous W.G. Low House in Bristol, RI, designed by McKim, Mead, White in 1887.brbrThis house was built in 2003 with quality materials inside and out, and includes a three-car garage, a media/recreational room, and fantastic guest quarters on different levels. Top of the line appliances and granite counters in the kitchen, and central air throughout for modern living. It is located on one of the most beautiful roads in Lenox, MA.brbrTell the traveler about yourself: We are an architect and oncologist living in Miami, raising our 6 (now grown) kids.brbrWhy did you choose to buy a vacation rental in this location brbrHailing from Miami, Florida, we were introduced to the Berkshires over 30 years ago and have been returning annually ever since. We have family reunions here every winter as a great escape from the hustle and bustle of the city, while enjoying the rich cultural and historical attractions of the Berkshires.

Charming, spacious country home with stunning views.....steps from Tanglewood!

Lenox, Massachusetts, United States

5

Bed

5

Bath

8

Sleeps

$392.65

Enjoy a stylish experience at this cozy newly renovated two-bedroom mobile home in the Berkshires of Lenox, Massachusetts. Centrally located: 10 minutes from Tanglewood, 40 min to MASS MoCA, 20 min to Great Barrington, 25 min to Mt. Greylock. Shopping centers and great restaurants nearby. brQuiet and safe neighborhood

Cozy Home in Lenox

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$481.4

Welcome to where comfort meets convenience in the heart of the Berkshires! Just 1.5 miles from Tanglewood, 5 minutes to Kripalu, and less then a mile to downtown Lenox, you'll have easy access to arts, unique shops, cozy cafés, fine dining, and world-class events.br brOutdoor enthusiasts will love skiing at nearby Bosquet, Butternut, and Jiminy Peak, while warmer months bring opportunities for lakes, hiking, boating, and golfing. Whether you seek adventure or relaxation, this home has it all!brbrThis charming two-story home combines modern comfort with timeless elegance, making it the perfect retreat for family and friends. brbrMain Level:brThe main level features stunning wood floors that flow seamlessly throughout. A recently renovated, fully-equipped kitchen with a gas cooktop opens to the living and dining areas, providing comfortable seating for six—ideal for shared meals and gatherings. Adjacent to the common areas, a cozy den offers a dedicated desk and work space for those needing to stay connected. Other conveniences on the first floor include a screened-in porch for relaxed outdoor enjoyment, a mudroom, a half bath, and a laundry room.brbrUpstairs:brThe second level boasts a spacious master bedroom suite, designed for ultimate comfort and relaxation. Across the hall, you’ll find two generously sized bedrooms that share a well-appointed bathroom, offering plenty of space and privacy for guests or family members.brbrOutdoor Spaces:brStep outside to a private, fenced-in backyard that feels like an oasis, with a forested greenspace beyond for added tranquility. Enjoy cooler evenings gathered around the firepit or dining al fresco under the lights in the outdoor dining area. The property also includes a two-car garage and ample parking, along with plenty of storage for sporting equipment or outdoor gear.brbrModern Amenities:brThis beautifully furnished home is equipped with all the modern conveniences you need for a relaxing stay, including high-speed Wi-Fi, speakers, and Smart TVs. Its prime location in the heart of the Berkshires puts you close to local attractions, making it an ideal base for exploring the region. brbrWhether you're planning a family getaway or a trip with friends, this home offers the perfect blend of style, functionality, and warmth to create lasting memories.brbrbrLocal AttractionsbrbrDowntown Lenox: 0.9 MilesbrTanglewood: brWyndhurst Golf Course and Country Club: brCanyon Ranch, Resort and Spa:brBosquet Mountain: brButternut Ski Resort:brJiminy Peak Mountain Resort:brKennedy Park:brOctober Mountain:brNorman Rockwell Museum:brBerkshire Scenic Railway Museum: 1.1 Miles brLenox Library: 1.3 Miles brVentfort Hall: 1.5 Miles brThe Mount - Edith Wharton's Home: 2.3 Miles brFrelinghuysen Morris House & Studio: 2.4 Miles brTanglewood Theatre: 2.9 Miles brKripalu Center for Yoga and Health: 3.5 Miles brPleasant Valley Wildlife Sanctuary: 3.8 Miles brBerkshire Botanical Garden: 7 Miles brNaumkeag: 7 Miles brHousatonic River Walk: 13.8 Miles

Lenox Gem with AC!

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$373.22

Retreat to this spacious 2-bedroom condo at The Ponds at Foxhollow, nestled in the scenic Berkshires of Massachusetts. Perfect for families or small groups, this peaceful escape offers a pond-view deck, a full kitchen, fireplace, and access to resort amenities like indoor/outdoor pools and a fitness center. Explore hiking trails, waterfalls, and cultural gems nearby. Unwind with stunning views, cozy interiors, and a wealth of year-round outdoor recreation right at your doorstep.brbr• Scenic Pond Viewbr• Fireplace & Smart TVbr• Indoor & Outdoor Poolsbr• Full Kitchen & Dining Areabr• Deck Overlooking Pondbr• Free Wi-Fibr• Access to Trails & WaterfallsbrbrWelcome to this spacious 2-bedroom apartment, perfect for families or groups seeking a relaxing nature-filled retreat.brbr• Master Bedroom: King-size bed, en-suite bathroombr• Second Bedroom: Two twin beds, closet spacebr• Living Area: Double sleeper sofa, fireplace, Smart TVbr• Kitchen: Fully equipped, dining area, coffee makerbr• Bathroom: Shower/tub combo, towels, toiletriesbr• Deck: Pond view, outdoor seatingbrbrOther amenities available at The Ponds at Foxhollow include (but are not limited to):brbr• Indoor and outdoor poolsbr• Fitness centrebr• Shared BBQ areabr• Games roombr• Wi-Fi throughout the resortbrbrLOCAL FAVORITESbrbrFood & Drinkbrbr• Nudel Restaurant: Farm-to-table cuisine in a stylish setting – 3.2 mibr• Alta Wine Bar: Mediterranean-inspired dishes with local wines – 3.4 mibr• Bistro Zinc: Classic French bistro ambiance with seasonal menus – 3.3 mibrbrOutdoor Activitiesbrbr• Monument Mountain: Hike scenic trails with valley views – 8.5 mibr• Mass Audubon Pleasant Valley: Birdwatching and forest trails – 3.9 mibr• Kennedy Park: Jogging, walking, and nature trails – 2.1 mibrbrRecreational Activitiesbrbr• The Mount, Edith Wharton’s Home: Explore a historic mansion and gardens – 2.9 mibr• Norman Rockwell Museum: American illustration exhibits – 7.2 mibr• Tanglewood: Live outdoor music venue – 4.3 mibrbrOTHER THINGS TO NOTE:br• Parking: Only one parking space per unit. No trailers or motorcycles allowed. Parking pass required at all times.br• Pet Policy: Only ADA Service Animals are permitted; no other pets allowed.br• Smoking: Strictly prohibited. Violations may result in fines up to $1,000 and eviction.br• Quiet hours from dusk to dawn. Late departures may result in fees.br• Room assignments may differ from the photos, as each unit is unique.br• Guests must be 21+ and present valid ID at check-in. Reservation must be under the staying guest's name.br• Only artificial logs may be used in fireplaces.br• Washer and dryers may only be used between 9 AM and 9 PM.br• Guests are liable for damages or excess cleaning. A pre-authorization hold will be placed on your credit card.br• Please turn off lights and HVAC when leaving to help conserve energy.br

Condo

Tranquil Lakeside Escape in the Berkshires

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$310.81

Escape to a serene retreat at this cozy 1-bedroom condo in The Ponds at Foxhollow, nestled in the heart of the Berkshires. With a scenic pond view and surrounded by breathtaking mountains, this charming unit is perfect for couples or small families seeking tranquility. Enjoy a fully equipped kitchen, warm fireplace, and access to indoor and outdoor pools, along with endless nearby hiking trails and cultural activities. Your perfect getaway awaits in beautiful Lenox, MA.brbr• Pond Viewsbr• Indoor & Outdoor Poolsbr• Fully Equipped Kitchenbr• Fireplace & Living Areabr• Free Wi-Fi & Smart TVbr• Proximity to Hiking Trailsbr• Peaceful Setting in BerkshiresbrbrWelcome to this charming 1-bedroom condo, perfect for couples or small families seeking a scenic retreat.brbr• Master Bedroom: King-size bed, en-suite bathroombr• Living Area: Double sleeper sofa, fireplace, Smart TVbr• Kitchen: Full appliances, coffee maker, dining areabr• Bathroom: Shower/tub combo, towels, essentialsbr• Deck: Overlooking the pond, outdoor seatingbrbrOther amenities available at The Ponds at Foxhollow include (but are not limited to):brbr• Indoor pool (shared)br• Outdoor pool (summer only)br• Fitness Centrebr• Shared BBQ areabr• Games room/areabrbrLOCAL FAVORITESbrbrFood & Drinkbrbr• Nudel Restaurant: Farm-to-table cuisine in a stylish setting – 3.2 mibr• Alta Wine Bar: Mediterranean-inspired dishes with local wines – 3.4 mibr• Bistro Zinc: Classic French bistro ambiance with seasonal menus – 3.3 mibrbrOutdoor Activitiesbrbr• Kennedy Park: Family-friendly trails for walking and jogging – 2.1 mibr• Monument Mountain: Scenic hike with valley views – 8.5 mibr• Mass Audubon Pleasant Valley: Forest and wetland hikes – 3.9 mibrbrRecreational Activitiesbrbr• Tanglewood: Iconic music venue hosting summer concerts – 4.3 mibr• Norman Rockwell Museum: Celebrates American illustration – 7.2 mibr• The Mount, Edith Wharton’s Home: Historic estate and gardens – 2.9 mibrbrOTHER THINGS TO NOTE:br• Parking: Only one parking space per unit. No trailers or motorcycles allowed. Display your parking pass at all times.br• Pet Policy: Only ADA Service Animals permitted. No other pets allowed.br• Smoking: Strictly prohibited. Fines up to $1,000 and eviction may apply.br• Quiet hours are from dusk to dawn. Late departures may incur penalties.br• Room assignments may differ from the photos, as each unit is unique.br• Guests must be 21+ to book and must occupy the unit. ID is required at check-in.br• A pre-authorized damage deposit will be held on your credit card. Guests are liable for damages or excess cleaning.br• Only artificial logs may be burned in fireplaces.br• Washer and dryers may only be used between 9 AM and 9 PM.br

Condo

Peaceful 1BR Condo with Pond View

Lenox, Massachusetts, United States

Bed

Bath

4

Sleeps

$330.0

New on the rental market for 2026, this fully-furnished 3-bedroom, 2-car garage townhome features 3 1/2 bathrooms, a leisure room with a treadmill, and cathedral ceiling in the dining and living room areas. Stunning views of the valley and hills across the valley towards the Stockbridge Bowl. Enjoy the views from exterior upper and lower decks, or from the indoor comfort of AC. Shared use of HOA outdoor pool and pickleball courts. 5-min drive to Tanglewood, and walking distance to downtown Lenox. Relax in a peaceful setting that feels like a true home away from home. Alas, no pets allowed. And HOA restrictions include no smoking or vaping of any kind; 3-month minimum rental period; and HOA approval of renters. If you are interested in longer than 3-months, then please contact me and I can provide a larger discount. Looking forward to hosting you.

3-bedroom furnished townhome near Lenox, beautiful views, 3 month min rental

Lenox, Massachusetts, United States

3

Bed

3

Bath

6

Sleeps

$921.84

Summary:brbrStay tonight and book two houses across the street from each other—perfect for large families! Together: 8 bedrooms, 5 baths, private lake access, dock, kayaks, and space for 18 guests. The main home is newly renovated with 4 beds, 3 baths, and lakeside views. Enjoy year-round fun: swimming, kayaking, fishing, ice skating, or just relaxing. It’s ideal for reunions, celebrations, and multi-generational getaways.brbrbrbrThe Space:brbrWelcome to your exclusive lakeside estate in the heart of Lenox, Massachusetts, the perfect setting for large family gatherings, reunions, and multi-generational getaways. This rare property offers two fully equipped homes on a private lakefront lot, blending peaceful seclusion with modern comfort. Whether you’re hosting a milestone celebration, enjoying a holiday with loved ones, or simply seeking a serene escape, this retreat offers unmatched space, flexibility, and natural beauty.brbrbrbrThe Main Lake House sleeps up to 10 guests and features four spacious bedrooms and three full bathrooms. The private primary loft includes a queen bed and ensuite bathroom. Two additional second-floor bedrooms, each with queen beds, share a renovated bathroom, while the first floor hosts a large bedroom with two queen beds and a nearby full bathroom, easily accessible with minimal stairs.brbr brbrMain House Bedroom Breakdown:brbrBedroom 1 (Primary Loft, 2nd Floor): Queen bed with ensuite bathroombrbrBedroom 2 (2nd Floor): Queen bedbrbrBedroom 3 (2nd Floor): Queen bedbrbrBedroom 4 (1st Floor): Two queen bedsbrbrbrbrThe home’s beautifully updated chef’s kitchen boasts maple cabinetry, granite countertops, stainless steel appliances, and an island for extra seating. The adjacent dining area accommodates ten, perfect for shared meals. A spacious living room with a smart TV to log into your favorite streaming apps, wood-burning fireplace, and grand piano offers space to gather, while the three-season porch features additional seating, a breakfast table, and a foosball table.brbrbrbrThe Guest House provides additional privacy and comfort for larger groups, sleeping up to eight more guests and offering two full bathrooms. The primary bedroom offers a king bed and ensuite bathroom with a stand-up shower. The second upstairs bedroom includes a queen bed and two twin beds, while the first floor has a queen bedroom and a full bedroom, sharing a full bathroom with a tub and shower combination.brbr brbrGuest House Bedroom Breakdown:brbrBedroom 1 (2nd Floor): King bed with ensuite bathroombrbrBedroom 2 (2nd Floor): Queen bed and two twin bedsbrbrBedroom 3 (1st Floor): Queen bedbrbrBedroom 4 (1st Floor): Full bedbrbrbrbrThe guest house living room offers stunning lake views and a smart TV to log into your favorite streaming apps, with an additional lounge off the kitchen featuring a wood-burning fireplace. The fully stocked kitchen includes stainless steel appliances, gas stove, espresso machine, fondue set, and extensive cookware. The dining area comfortably seats ten.brbrbrbrBoth homes offer central air conditioning, hardwood floors, and seamless indoor-outdoor living. Step outside to enjoy private lake access via a dock and rustic path, perfect for kayaking, swimming, fishing, or even ice skating in winter. Two kayaks and four life jackets are available for your use. The front deck of the guest house offers a four-burner gas grill and an outdoor dining table for ten. Large yards and beautifully landscaped grounds provide plenty of space for games and gatherings. Parking is ample, with space for up to eight vehicles.brbrbrbrIn the winter, you’re just minutes from some of the Berkshires’ best ski resorts. Bousquet and Ski Butternut are close by, with Lenox about 12 minutes away, Great Barrington around 20 minutes, Catamount in Egremont about 30 minutes, and Jiminy Peak roughly 35 minutes, giving you plenty of options for a great day on the slopes.brbrbrbrThis unique lakeside compound offers the perfect backdrop for creating lifelong memories with family and friends. Whether relaxing by the water, enjoying outdoor activities, or gathering for meals and celebrations, you’ll experience comfort, privacy, and the natural beauty of the Berkshires year-round. Book your next large family getaway today and discover the magic of Lenox!brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrThe Neighborhood:brbrLenox is centrally located in the Berkshires. It is well known for its restaurants and is at the center of the locally-grown food movement (check out Berkshire Grown for more info on our region’s farms). The summer home of the Boston Symphony Orchestra is Tanglewood, which spans both Lenox and Stockbridge and attracts fans of great classical and contemporary music to the region. Other cultural highlights in the area include the Jacob’s Pillow dance festival and Shakespeare & Company theater festival.brbrbrbrNot-to-miss gilded-age jewels of Lenox are The Mount, Edith Wharton’s Home (walking distance from the house), with over 50 beautiful acres, 2 gardens, and an historic home and museum, and Ventfort Hall, a lovingly restored property with a fascinating history reaching back to the civil war.brbrbrbrLenox is home to a multitude of culinary options with favorites such as Bistro Zinc (French fare in a chic dining room with a hopping bar scene) and Alta (Buzzing eatery/wine bar offering a Mediterranean menu & a covered porch for outdoor dining).brbrbrbrOther activities within walking distance or short kayak trip away:brbr-The Mount: Edith Wharton’s estate and beautiful gardensbrbr-Lee Town Beachbrbr-Lenox Town Beachbrbr-High Lawn Farm (watch baby cows be born and grow!)brbr-Shakespeare & Company campusbrbr-Canyon Ranch spa and parkbrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying and being respectful of the neighbors apply.brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.brbr*Damage caused by pets is not covered by the accidental damage waiver.

Lakeside Estate: 2 Homes For Family Gatherings

Lenox, Massachusetts, United States

Bed

Bath

Sleeps

$486.5

Summary:brbrNewly renovated lakefront getaway on beautiful and serene Laurel Lake in Lenox! This spacious 4-bedroom, 3-bath home sleeps 10 and features a modern kitchen, grand piano, wood-burning fireplace, and enclosed 3-season porch. Enjoy stunning lake views, direct access, a private dock, and plenty of indoor and outdoor space to relax. Ideal for families or groups, with parking for 4 and all the comforts of home in a scenic, peaceful setting.brbrbrbrThe Space:brbrWelcome to your newly renovated lakeside escape in Lenox,—a perfect blend of modern comfort and classic New England charm . Nestled literally 5 steps from the edge of serene Laurel Lake, this peaceful and private home invites you to unwind, explore, and reconnect with nature. Whether you’re sipping your morning coffee while listening to the sounds of the water or enjoying the sunset by the dock, this property delivers an unforgettable Berkshires experience.brbrbrbrThis thoughtfully updated home features four spacious bedrooms and three full bathrooms, comfortably sleeping up to 10 guests. It’s perfect for multi-generational families, groups of friends, or anyone seeking a scenic retreat with easy access to the outdoors.brbrbrbrUpstairs, you’ll find a private primary loft with a queen bed and ensuite bathroom with shower, vanity, and toilet. Two additional second-floor bedrooms, each with a queen bed, share a beautifully renovated bathroom with double vanity, spacious shower, toilet, and washer/dryer. The first floor includes a fourth bedroom with two queen beds and an adjacent full bathroom featuring a double vanity, tub/shower combo, and toilet—ideal for guests looking to avoid stairs, with just five steps to the front door and no interior stairs required to access this space.brbrbrbrFor easy planning, here are the bedroom layouts:brbrBedroom 1 (Loft): Queen bed with en suite bathroom (2nd floor)brbrBedroom 2: Queen bed (2nd floor)brbrBedroom 3: Queen bed (2nd floor)brbrBedroom 4: Two queen beds (1st floor)brbrbrbrAt the heart of the home is a beautifully updated chef’s kitchen, equipped with maple cabinetry, granite countertops, a center island with bar seating for three, and high-end stainless steel appliances—including a gas stove, dishwasher, and microwave. The adjacent dining area seats ten, making it the perfect space for shared meals and celebrations.brbrbrbrThe living room offers a warm and inviting space to relax, with a giant smart TV for streaming, a wood-burning fireplace, a Yamaha grand piano, and comfortable seating. Step into the three-season sun room, where you’ll find more seating, a breakfast table, and a foosball table—perfect for relaxing, playing games, or enjoying views of the surrounding nature.brbrbrbrOutdoors is where this property truly shines. With direct lake access, a private dock, and unmatched water views, you can spend your days swimming, kayaking, or simply relaxing by the shoreline. Grill up lunch on the propane BBQ, enjoy dinner al fresco, or watch the stars reflect off the peaceful lake. This outdoor space is perfect for both quiet reflection and memorable gatherings.brbrbrbrIn the winter, you’re just minutes from some of the Berkshires’ best ski resorts. Bousquet and Ski Butternut are close by, with Lenox about 12 minutes away, Great Barrington around 20 minutes, Catamount in Egremont about 30 minutes, and Jiminy Peak roughly 35 minutes, giving you plenty of options for a great day on the slopes.brbrbrbrIn the winter, the home is only minutes away from the best ski resorts in the Berkshires. You'll find Bousquet, Lenox (12min), Butternut, Great Barrington (20min), Catamount, Egremont (30min) and Jimminy Peak (35min) all within driving distance for some great skiing! brbrbrbrThe home features beautiful hardwood floors throughout, central air conditioning, and hybrid heatpump/propane heat for year-round comfort. Parking is available for up to four cars in two tandem spots.brbrbrbrWhether you're looking for a peaceful weekend escape or a longer stay to enjoy all the Berkshires have to offer, this newly renovated lakefront home combines natural beauty, thoughtful amenities, and a prime location to create the perfect Lenox getaway.brbrbrbrOur neighbor has an EV charger that guests can use for free, subject to availability and a six hour charging window. Reach out if you’d like details.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrThe Neighborhood:brbrLenox is centrally located in the Berkshires. It is well known for its restaurants and is at the center of the locally-grown food movement (check out Berkshire Grown for more info on our region’s farms). The summer home of the Boston Symphony Orchestra is Tanglewood, which spans both Lenox and Stockbridge and attracts fans of great classical and contemporary music to the region. Other cultural highlights in the area include the Jacob’s Pillow dance festival and Shakespeare & Company theater festival.brbrbrbrNot-to-miss gilded-age jewels of Lenox are The Mount, Edith Wharton’s Home (walking distance from the house), with over 50 beautiful acres, 2 gardens, and an historic home and museum, and Ventfort Hall, a lovingly restored property with a fascinating history reaching back to the civil war.brbrbrbrLenox is home to a multitude of culinary options with favorites such as Bistro Zinc (French fare in a chic dining room with a hopping bar scene) and Alta (Buzzing eatery/wine bar offering a Mediterranean menu & a covered porch for outdoor dining).brbrbrbrOther activities within walking distance or short kayak trip away:brbr-The Mount: Edith Wharton’s estate and beautiful gardensbrbr-Lee Town Beachbrbr-Lenox Town Beachbrbr-High Lawn Farm (watch baby cows be born and grow!)brbr-Shakespeare & Company campusbrbr-Canyon Ranch spa and parkbrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! Standard rules like no smoking, no partying, no pets and being respectful of the neighbors apply. No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

Lakefront, Kayaks Included, Come Unwind In Lenox!

Lenox, Massachusetts, United States

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$457.08

Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless steel appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware and dishes. The living room features a cozy setup with a smart tv, all you need is your passwords and logins for your streaming devices. High speed WIFI is also available throughout the space. Central heat and AC provide a comfortable relaxing environment. brLocated on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless steel appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware and dishes. The living room features a cozy setup with a smart tv, all you need is your passwords and logins for your streaming devices. High speed WIFI is also available throughout the space. Central heat and AC provide a comfortable relaxing environment.

Apartment

Main Street Delight 1bedroom

Lenox, Massachusetts, United States

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$497.07

Autumn 2025! Come enjoy the fall color in the Berkshires / Lenox in this walk-to- town vintage charmer. Minimum 4 night stay - with a Thursday turnover/housekeeping day. Check-in on Thursday/Friday/Saturday and stay for 4+ nights. Weekly, Monthly & Seasonal stays are welcome. Positively fragrant with charm, hidden by blooming trees and flowers, we've everything you need for enjoying the arts and nature from this central location. House is uniquely elegant, creative, filled with art, sunlight and comforts. Screen porch is wonderful on the warmer days.br Pets - Small dogs (only) under 25 pounds may be considered but only after receiving up-to-date vet records showing your pup is in great health. But please note that dogs are not permitted on the beds or the furniture. No events please.

New for 2025! Walk to Lenox Village - 1930s Cottage Charmer!

Lenox, Massachusetts, United States

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$924.35

Evergreen Home Vacation Rentals invites you to this spacious 4-bedroom home on a quiet cul-de-sac beneath October Mountain. The picturesque backyard features a private heated in-ground pool and abuts a 10-acre “meditation meadow” for year-round peace.brbrLocated just 10 minutes from Lenox and Tanglewood, and 7 minutes to Bousquet Mountain, you are steps away from shops and dining. Enjoy a centrally located retreat perfect for the whole family. Experience the best of the Berkshires today!brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrPeaceful Lenox neighborhood, just a quick drive to downtown. brbrFront door uses a key, but you’ll have the keypad code to the garage so you can enter that way and avoid any inclement weather. Only one step up from garage into kitchen. Plenty of parking on the long, flat driveway.brbrAt 3,000 sq. ft., this 4-bedroom, 2.5 bath home offers room for everyone and comfortably sleeps 8. Great for a large family or several couples. The recent renovations included brand-new hardwood floors throughout the home.brbrThe main floor features a large sun-filled, fully-equipped kitchen with breakfast table, a comfy den with a fireplace and new 65” TV, a half bathroom, and laundry. Off the center entry hall is the spacious living room with an additional 65 TV. The all-glass sun-room provides the featured warm-weather dining area overlooking the pool, yard, and meadow, while the formal dining room serves large groups in cooler weather. brbrUpstairs are 4 bedrooms (3 queen, 1 full) and 2 bathrooms. The large Primary bedroom contains a sitting area, walk-in closet, and huge skylight bathroom featuring a 2-person jacuzzi tub. Upstairs find 3 desks: 1 in each guest bedroom and a secretary desk in the nook.brbrEntertainment includes every major streaming service on 2 new big-screens, a portable blue tooth speaker, and a selection of puzzles. Enjoy Netflix, Prime, Hulu, HBO Max, Showtime, ESPN, Disney, and major networks (just use the Guest Profile please). You will find a variety of board games for exciting game nights and a ping pong table in the basement. brIn the summer, we offer central A/Cs to keep cool during those warm nights.brbrThe back yard features a large heated in-ground pool, chaise lounges, patio seating, a new Weber grill, and plenty of yard space for games like the Cornhole set stored in the garage! brbrGuests will feel like they are in their own private oasis, yet only a short drive North or South to amazing Berkshire attractions like Mass MoCa, Tanglewood, Red Lion Inn, and wineries like Balderdash Cellars. Skiing at Bousquet is 5 minutes away, while Butternut, Catamount, and Jiminy Peak Ski resorts are 30 minutes away. Relax or Kayak at any of 6 lakes that are all 10 to 20 minutes away. Hiking trails abound in every direction, including Kennedy Park in Lenox 6 minutes away. Enjoy a spa day or play 18 at the Miraval Resort only minutes away, and take in amazing performance at Berkshire Theatre Festival, Shakespeare & Co, or Barrington Stage.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: Located in a peaceful Lenox neighborhood, just a quick drive to downtown shops, restaurants, and attractions.brbr⭐️ PETS: Dogs may be permitted with prior owner approval. Not all dogs will be approved. No multiple pets allowed. A $100 pet fee applies if approved.brbr⭐️ PARKING: Free parking is available on the premises.brbr⭐️ POOL: Open seasonally from May through October, with exact dates determined by weather.br• June 1 through Labor Day: Heated to 82°F at no additional cost. Guests may request a higher temperature for an additional fee—please contact us in advance.br• May & after Labor Day: Pool heating may be available for $150 per day, but is not guaranteed. Advance notice is required to ensure the pool is ready.br• Heating above 82°F during June–Labor Day is available for an additional fee—please contact us in advance to confirm.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.

Lenox Grand Colonial with Pool by Evergreen Home

Lenox, Massachusetts, United States

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Sleeps

$357.44

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. Provided are pots, pans, cooking utensils, glassware, flatware, dishes . 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.brLocated 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. Provided are pots, pans, cooking utensils, glassware, flatware, dishes . 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.

Apartment

Renovated Downtown 1bedroom

Lenox, Massachusetts, United States

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