Winthrop Estate – An Elegant Home

Photo gallery for Winthrop Estate – An Elegant Home

A traditional stone house with a central entrance, a gravel driveway, and a well-maintained garden.
A sunlit room with wicker furniture, potted plants, and a view of palm trees through a window.
A spacious living room with a large sofa, armchairs, a coffee table, and a fireplace. There are bookshelves and a chandelier.
A well-maintained lawn with stone walls and flower planters, surrounded by tall trees and a clear sky.
A formal dining room with multiple round tables set for a meal, large windows with curtains, and a chandelier.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Lenox Library

Popular amenities

  • Balcony
  • On-site fitness centre
  • Toys
  • Barbecue
  • Electric vehicle charging point
  • Air-conditioning

Explore the area

View map
Lenox, MA
  • Place, Lenox Library
    ‪16 min walk‬
  • Place, Ventfort Hall Mansion and Gilded Age Museum
    ‪3 min drive‬
  • Place, Berkshire Performing Arts Center
    ‪3 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪54 min drive‬

Rooms & beds

12 bedrooms (sleeps 24)

Bedroom 1

1 King Bed and 1 Single Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed and 1 Single Bed

Bedroom 4

1 King Bed

Bedroom 5

1 Queen Bed

Bedroom 6

1 Queen Bed

Bedroom 7

2 Single Beds

Bedroom 8

1 Double Bed

Bedroom 9

1 Double Bed

Bedroom 10

2 Single Beds

Bedroom 11

1 Double Bed

Bedroom 12

1 Single Bed

10 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Bathtub · Toilet · Shower only

Bathroom 5

Bathtub · Toilet · Shower only

Bathroom 6

Bathtub · Toilet · Shower only

Bathroom 7

Bathtub · Toilet · Shower only

Bathroom 8

Bathtub · Toilet · Shower only

Bathroom 9

Bathtub · Toilet · Shower only

Bathroom 10

Bathtub · Toilet · Shower only

Bathroom 11

Toilet

Spaces

Kitchen
Office
Balcony
Garden

Add dates for prices

Similar properties

The Kemble - a registered Great Estate
The Kemble- Built by a US Secretary of State in Lenox
Lenox
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (20 reviews)
The Kemble- Built by a US Secretary of State in Lenox

About the area

Lenox

Lenox is home to this villa. 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. Travelling with kids? Consider Berkshire Performing Arts Center and Berkshire Scenic Railway Museum.
View more Villas in LenoxOpens in a new window
Map
Lenox, MA

What's nearby

  • Lenox Library - 16 min walk - 1.4 km
  • Ventfort Hall Mansion and Gilded Age Museum - 3 min drive - 1.8 km
  • Berkshire Performing Arts Center - 3 min drive - 1.8 km
  • Tanglewood Music Center - 4 min drive - 2.9 km
  • The Mount - 6 min drive - 4.6 km

Getting around

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

Restaurants

  • ‪Antimony Brewing - Craft Brewery & Kitchen - ‬4 min drive
  • ‪Tanglewood Cafe - ‬6 min drive
  • ‪Bistro Zinc - ‬14 min walk
  • ‪Haven Cafe & Bakery - ‬11 min walk
  • ‪Chocolate Springs Cafe - ‬4 min drive

Frequently asked questions

Is Winthrop Estate – An Elegant Home pet-friendly?

No, pets are not allowed at this property.

How much is parking at Winthrop Estate – An Elegant Home?

On-site parking is available at the property.

What time is check-in at Winthrop Estate – An Elegant Home?

Check-in begins at 4:00 PM.

What time is check-out at Winthrop Estate – An Elegant Home?

Checkout is at 11:00 AM.

Where is Winthrop Estate – An Elegant Home located?

This family-friendly Lenox villa is within 1 mi (2 km) of Lenox Library, Berkshire Performing Arts Center and Ventfort Hall Mansion and Gilded Age Museum. Tanglewood Music Center and Wyndhurst Golf & Club are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a unique and cool house and property! Our family had a wonderful time celebrating a milestone birthday there.
Stayed 3 nights in Nov 2025
Response from VrboOwner on 2 December 2025
Thank you! With the many rooms for social time and quality time with family, The Winthrop Estate is well set up for milestone birthdays (and other multi-generational gatherings)! From the elegant dining room to the Tornado foosball table, the ping pong room, Lego collection, Rogue rack of weights, Solo stove under the stars and wood- paneled library, everyone has something to enjoy. :-)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful for our extended family gathering. Interesting opportunity to stay in a home from the Gilded Age, yet one equipped with all the modern conveniences. Jamie was an excellent and very responsive host, who provided great recommendations for local farmstands, kayaking, and bakery. Lots of spots for gathering in large groups, small groups and quiet time away from groups. The property had everything we needed (and then some). The yard was great for the 5-year and the rest of us to play lots of games (many provided with the property).
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our family reunion this past 4th of July weekend at the Winthrop Estate was nothing short of exceptional. The estate is absolutely stunning—beautifully maintained, rich in history, and the perfect setting for bringing generations of family together. Every detail exceeded our expectations, but what truly made the experience special was Jamie. She was an incredibly gracious, thoughtful, and attentive host who made us feel welcome from the moment we arrived. We created memories that will stay with our family for a lifetime, and we cannot recommend the Winthrop Estate highly enough.
Stayed 4 nights in Jul 2026
Tell us how we can improve our siteShare feedback