Entire home

Lakeside Estate: 2 Homes For Family Gatherings

Photo gallery for Lakeside Estate: 2 Homes For Family Gatherings

Exterior
Exterior
Exterior
Private kitchen
Games room
8 bedrooms5 bathroomsSleeps 18

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace
  • Barbecue grill
  • Kitchen

Explore the area

Map
Lenox, Massachusetts
  • The Mount
    ‪18 min walk‬
  • Ventfort Hall Mansion and Gilded Age Museum
    ‪5 min drive‬
  • Tanglewood Music Center
    ‪8 min drive‬
  • Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪17 min drive‬

Rooms & beds

8 bedrooms (sleeps 18)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Queen Beds

Bedroom 5

1 King Bed

Bedroom 6

2 Single Beds and 1 Queen Bed

Bedroom 7

1 Queen Bed

Bedroom 8

1 Double Bed

5 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Garden
Dining area

About this property

Lakeside Estate: 2 Homes For Family Gatherings

Summary:
Stay 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.

The Space:
Welcome 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.

The 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.

Main House Bedroom Breakdown:
Bedroom 1 (Primary Loft, 2nd Floor): Queen bed with ensuite bathroom
Bedroom 2 (2nd Floor): Queen bed
Bedroom 3 (2nd Floor): Queen bed
Bedroom 4 (1st Floor): Two queen beds

The 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.
The 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.

Guest House Bedroom Breakdown:
Bedroom 1 (2nd Floor): King bed with ensuite bathroom
Bedroom 2 (2nd Floor): Queen bed and two twin beds
Bedroom 3 (1st Floor): Queen bed
Bedroom 4 (1st Floor): Full bed

The 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.

Both 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.

This 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!

The Neighborhood:
Lenox 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.

Not-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.

Lenox 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).

Other activities within walking distance or short kayak trip away:
-The Mount: Edith Wharton’s estate and beautiful gardens
-Lee Town Beach
-Lenox Town Beach
-High Lawn Farm (watch baby cows be born and grow!)
-Shakespeare & Company campus
-Canyon Ranch spa and park

Other Things to Note:
We look forward to welcoming you soon!
Standard rules like no smoking, no partying 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.
*Damage caused by pets is not covered by the accidental damage waiver.

Property manager

Lucas
Premier Host

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor space
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property

About the area

Lenox

Located in Lenox, this holiday home is on a lake. Wyndhurst Golf & Club and Wood's Pond are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Lee Premium Outlets and Guido's Marketplace. The Bookstore and Berkshire Scenic Railway Museum are also worth visiting.
Map
Lenox, Massachusetts

What's nearby

  • The Mount - 18 min walk - 1.5 km
  • Shakespeare and Company - 4 min drive - 3.2 km
  • Ventfort Hall Mansion and Gilded Age Museum - 5 min drive - 3.6 km
  • Tanglewood Music Center - 8 min drive - 6.1 km
  • National Shrine of the Divine Mercy - 12 min drive - 8.9 km

Getting around

  • Pittsfield Intermodal Transportation Center - 18 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 24 min drive

Restaurants

  • ‪McDonald's - ‬24 min drive
  • ‪Vivaldi's Pizzeria - ‬7 min drive
  • ‪51 Park Restaurant & Tavern - ‬7 min drive
  • ‪The Locker Room - ‬6 min drive
  • ‪Red Apple - ‬8 min drive

Frequently asked questions

Is Lakeside Estate: 2 Homes For Family Gatherings pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Lakeside Estate: 2 Homes For Family Gatherings?

Check-in begins at 4:00 PM.

What time is check-out at Lakeside Estate: 2 Homes For Family Gatherings?

Checkout is at 11:00 AM.

Where is Lakeside Estate: 2 Homes For Family Gatherings located?

Situated on a lake, this holiday home is within a 15-minute walk of Wyndhurst Golf & Club and The Mount. Shakespeare and Company and Housatonic River are also within 3 miles (5 km).

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About the host

Hosted by Lucas

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Premier Host

They consistently provide great experiences for their guests
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