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Winthrop Estate - 1925 Charm & Modern Luxury

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Exterior
Exterior
Exterior
Exterior
Exterior

Reviews

10 out of 10
Exceptional
12 bedrooms10+ bathroomsSleeps 24

Popular amenities

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

Explore the area

Map
Lenox, MA
  • Shakespeare and Company
    ‪4 min drive‬
  • Tanglewood Music Center
    ‪4 min drive‬
  • The Mount
    ‪6 min drive‬
  • Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪12 min drive‬

Rooms & beds

12 bedrooms (sleeps 24)

Bedroom 1

1 Twin Bed and 1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Twin Bed and 1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 Queen Bed

Bedroom 6

1 Queen Bed

Bedroom 7

2 Twin Beds

Bedroom 8

1 Double Bed

Bedroom 9

1 Double Bed

Bedroom 10

2 Twin Beds

Bedroom 11

1 Double Bed

Bedroom 12

1 Twin Bed

10 bathrooms, 1 half bathroom

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Bathroom 7

Toilet · Shower only

Bathroom 8

Toilet · Shower only

Bathroom 9

Toilet · Shower only

Bathroom 10

Toilet · Shower only

Bathroom 11

Toilet

Master Bathroom

Bathtub · Toilet · Shower only

Petit Boudoir Bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Office
Balcony
Garden
Dining area

About this property

Winthrop Estate - 1925 Charm & Modern Luxury

Summary:
I’m Jamie, the proud caretaker of the timeless and beautiful Winthrop Estate. This restored 1920s Gilded Age mansion, set on 45 serene acres with walking trails, blends historic charm with modern luxury. Perfect for groups, it features luxurious bedrooms, a chef’s kitchen, modern amenities, and elegant gathering spaces—an ideal retreat for creating lasting memories.

The Space:
Thoughtfully renovated with modern touches, this jewel is set on 45 acres and offers the perfect blend of charm and convenience.

Location Highlights:
- Less than a mile from the center of Lenox, with its vibrant restaurants, cafes, bars, shops, and galleries.
- Within a mile of Kennedy Park, a 500-acre hardwood forest featuring:
- 15 miles of groomed trails for hiking, cross-country skiing, and picnics.
- A lookout point with breathtaking mountain vistas.
- Just 1.5 miles from Tanglewood’s front gate, making it an ideal, centrally located property.

Onsite Amenities:
- Grand Social Spaces:
- A purple-heartwood-paneled library.
- A plant-filled conservatory.
- Chef’s Kitchen:
- Fully equipped with a 10-burner Wolf stove and a suite of Wolf appliances.
- Outdoor Features:
- BBQ grill, fire pit, and stove.
- Whiffle ball and lawn croquet.
- Acres of hiking trails.
- Recreation & Workspaces:
- Game room with ping pong, foosball, Legos, and board games.
- Dedicated workstation with an external monitor and powered standing desk.

Accommodations:
- 7 main bedrooms comfortably accommodate 14 guests.
- 5 additional standard bedrooms with a shared bathroom can host 10 more guests.
- Total capacity: 24 guests.
- A dining room with seating for up to 24 people.

Note:
While the estate is spacious and perfect for group gatherings, we do not host outside events with non-resident guests such as ceremonies or dinners.

Enjoy the perfect mix of historic elegance and modern comfort at the Winthrop Estate!

Other Things to Note:
To ensure a seamless and secure experience, all guests will be screened prior to check-in and asked to sign a house rules agreement.

Please keep in mind that the Winthrop Estate is nestled in the scenic countryside of Lenox. While we strive to maintain a clean and comfortable environment, the natural surroundings may include occasional encounters with flies and other wildlife. This is part of the charm of country living, and we appreciate your understanding.

We look forward to hosting you at the Winthrop Estate!

Interaction with Guests:
Once you have made your booking, we will give you our contact information and you can reach us before and during your stay. We are happy to share local information and house history.

Property manager

Jamie Berg

Languages

English, Spanish

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Gym
Outdoor Space

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House Rules

Check in after 4:00 PM
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
In addition to what is listed on Airbnb, we require all renters to agree to the following within 48 hours of booking. This Short Term Rental Agre...

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
Property Registration Number C0378281520

About the neighborhood

Lenox

Lenox is home to this vacation home. Guido's Marketplace and Lee Premium Outlets are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Pleasant Valley Wilderness Sanctuary and Fairfield Brook WMA. Traveling with kids? Consider The Bookstore and Berkshire Scenic Railway Museum.
Map
Lenox, MA

What's nearby

  • Lenox Library - 14 min walk - 1.2 km
  • Ventfort Hall Mansion and Gilded Age Museum - 4 min drive - 1.8 km
  • Shakespeare and Company - 4 min drive - 2.0 km
  • Tanglewood Music Center - 4 min drive - 2.6 km
  • The Mount - 6 min drive - 3.8 km

Getting around

  • Pittsfield Station - 16 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 12 min drive

Restaurants

  • ‪Guido's Fresh Marketplace - ‬7 min drive
  • ‪Burger King - ‬7 min drive
  • ‪Antimony Brewing - Craft Brewery & Kitchen - ‬3 min drive
  • ‪Joe's Diner - ‬10 min drive
  • ‪Mazzeo's Ristorante - ‬7 min drive

Frequently asked questions

Is Winthrop Estate - 1925 Charm & Modern Luxury pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Winthrop Estate - 1925 Charm & Modern Luxury?

Check-in begins at 4:00 PM.

What time is check-out at Winthrop Estate - 1925 Charm & Modern Luxury?

Check-out is at 11:00 AM.

Where is Winthrop Estate - 1925 Charm & Modern Luxury located?

This family-friendly Lenox vacation home is within a 15-minute walk of The Bookstore and Lenox Library. Tanglewood Music Center and Wyndhurst Golf & Club are also within 2 mi (3 km).

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About the host

Hosted by Jamie Berg

Host profile image
We spent an entire year traveling and visiting 20 countries and shortly thereafter decided to purchase this bucolic spot in the country. We spent the better part of a decade restoring the mansion to be both elegant and comfortable, maintaining the original layout and character of the estate while also seamlessly upgrading the underlying systems.

Why they chose this property

It's solitude. Its solidity. Its exquisiteness. Its history. Its location.

What makes this property unique

The craftsmanship of this property is unparalleled.
Its location in the absolute center of the cultural heart of the Berkshires.
We have a love of the area, there are various organizations we admire and appreciate, as well as craftsmen, artists and chefs and we are happy to introduce you to them to enhance your time in the Berkshires.

Languages:

English, Spanish