Entire home
Winthrop Estate - 1925 Charm & Modern Luxury
Photo gallery for Winthrop Estate - 1925 Charm & Modern Luxury





Reviews
10 out of 10
Exceptional
12 bedrooms10+ bathroomsSleeps 24
Popular amenities
Explore the area

Lenox, MA
- Shakespeare and Company4 min drive
- Tanglewood Music Center4 min drive
- The Mount6 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.
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
Children
Children allowed: ages 0-17
Events
No events allowed
Pets
No pets allowed
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
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.

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
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
Reviews
Reviews
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About the host
Hosted by Jamie Berg

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.
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
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