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Winthrop Estate, near Tanglewood, for luxury family vacations

Bedrooms 7
Half Baths1
Property type estate
Minimum Stay 3 nights


About the property

7 Bedrooms, 10 Baths, Sleeps 14+

Set on more than forty acres in the heart of Lenox, this gilded-age estate is available for your exclusive use year-round.

The main bedrooms are spacious and are beautifully appointed with hand-made Gardner mattresses from a third generation mattress maker, antiques, fine Frette linens, have individually controlled heat and air conditioning, and private baths.

The formal rooms include a wood-paneled library, a large music/living room with a Steinway grand piano and formal dining room with beautiful marble fireplaces, a conservatory with mountain views, a game room, an exercise room, and wireless internet. There is a ninety foot slate verandah and a six acre lawn with views of Lenox Mountain and the Berkshire hills.

Private chef, golf, tennis, croquet, horseback riding, hiking, massages, music lessons, in-house concerts, hot-air balloon rides and much more is available for an additional fee.

'We are still pinching ourselves': The mansion is so grand yet welcoming; every room, from the bedrooms, dining room, library and solarium takes on a special feeling of its own. And of course the grounds are astoundingly beautiful as well. We are still pinching ourselves asking 'Did that weekend really happen? Or were we dreaming?' And our 7 year old son, Billy, who fortunately gets exposed to many fun things, claims his stay at the mansion was the best weekend of his life!-- Donna and Jon

Wonderful weekend memories linger. A special part of those memories was your beautiful home, its ambiance and charm, and the terrific time everyone had there. Our kids were delighted. --Sidney

'The most impressive property in the area' -Frank: The Winthrop is truly as beautiful a property as one could ever imagine. When you step into the Winthrop you step back in time. You expect to turn the corner and find Robert Redford as the Great Gatsby handing you a gin and tonic on the veranda. It is far and away the most impressive property in the area, and we looked at and stayed at many.

It is a meticulously restored late 19th early 20th century mansion. It posses all the best qualities of both a private home and in Inn combined, and it is easily on par with any world-class 5-star establishment. But, fundamentally, it is simply a home (not an Inn or Hotel) and that is what makes it so tremendously unique and so wonderful. When you host an event at the Winthrop you feel, and your guests feel, like the event is taking place right in your own home (assuming that you lived in a giant mansion). It is a very different feeling and than taking over an Inn for the weekend, and we could not possibly recommend the experience more highly.

'Sumptuous grounds': Impeccable renovation and sumptuous grounds make this house the perfect dream place. So much love and care to the last detail! ~ Monique & Joe

More Details

Property Manager
Member since: 2007
Speaks: english
Calendar last updated:
February 13, 2017


Lenox Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
  • Housekeeper Included
House Rules:
  • Max. occupancy: 14
  • non smoking only ...
  • pets not allowed
  • children welcome ...
Location Type:
  • Downtown ...
  • Mountain
  • Mountain View ...
  • Town
  • Village ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Clothes Dryer
  • Filtered Water
  • Fireplace
  • Firewood
  • Fitness Room / Equipment
  • Garage
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Local Maps
  • Parking
  • Parking Off Street
  • Shampoo
  • Telephone
  • Towels Provided
  • Washing Machine
  • Water Cooler
  • Wireless Internet
  • fax
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Child's Highchair
  • Dining Room
  • seating for 32 people
  • 7 Bathrooms
  • 1 Half Bath
  • Master - toilet , combination tub/shower
    Botanical - toilet , combination tub/shower
    French - toilet , combination tub/shower
    West Wing - toilet , combination tub/shower
    Petite Boudoir - toilet , shower
    Library - toilet , First Floor
    Game Room - toilet , combination tub/shower , Third Floor
    Library - shower , First Floor
    Blue - toilet , combination tub/shower
  • All bathrooms have Molton Brown amenities. Most bathrooms have large antique English soaking tubs and solid nickel bath fixtures.
  • 7 Bedrooms, Sleeps 14
  • Master - 1 king , Two Fireplaces
    Botanical - 1 king , 1 twin/ single , Fireplace
    French - 1 king , Fireplace
    West Wing - 1 queen
    Blue - 1 king
    Southern West Wing Suite - 2 twin/ single
    Petite - 1 queen , Fireplace
  • All main bedrooms have separately zoned heat and air-conditioning, Frette linens, hand-crafted mattresses.
  • Audio Tape Player
  • Books
  • Books for Kids
  • CD Player
  • DVD Player
  • Foosball
  • Game Room
  • Games
  • Games for Kids
  • Music Library
  • Piano
  • Ping Pong Table
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • Toys
  • Video Game Console
  • Balcony ...
  • Barbecue
  • Beach Chairs
  • Child's Swing
  • Deck / Patio ...
  • Golf ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Patio
  • Ski & Snowboard ...
  • Tennis ...
  • Tennis Court
  • Terrace
  • 14 garden chairs
  • wheelchair inaccessible ...
Onsite Services:
  • Concierge
  • Daily Maid Service
  • autumn foliage
  • botanical garden
  • churches
  • cinemas
  • coin laundry
  • festivals
  • forests
  • library
  • live theater
  • museums
  • playground
  • pond
  • restaurants
  • synagogues
  • waterfalls
Leisure Activities:
  • antiquing
  • bird watching
  • eco tourism
  • horseback riding
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • sledding
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • hunting
  • ice skating
  • mountain biking
  • mountain climbing
  • roller blading
  • sailing
  • ski privileges optional
  • skiing
  • swimming
  • tennis
  • water skiing
  • water tubing


Exceptional! 5/5 -
(8 traveler reviews)

Winthrop Estate, near Tanglewood, for luxury family vacations
average rating of 5.0 based on 8 reviews

Luxurious Rockefeller-like New England mansion

  • 5 of 5

I travel extensively throughout the world for my work and have stayed at many of the worlds great hotels. Quite frankly, I was not expecting but was pleasantly surprised to discover a world class property in the tiny town of Lenox.

The Winthrop Estate is a perfect marriage of an historical Rockefeller-like New England mansion of the 1920s and a Four Seasons hotel of today. This is how we’d describe our stay at Winthrop Estate. The experience was nothing short of going back a hundred years to the days when The Berkshires were a pastoral retreat for the great Industrialists and statesmen of the day while enjoying the luxury of the current era. The Winthrop Estate is neatly tucked away, thus we experienced as little or as much of civilization as we desired. In the morning we took a walk to the center of Lenox (a sleepy but adorable typical New England town), which is just a five minutes away. We stopped at a bagel shop, then got coffee at a French patisserie, and then just walked and enjoyed the tranquility and simple beauty of this historic area.

The Winthrop Estate was a perfect place to decompress from the busyness of everyday life. We really enjoyed our stay and highly recommend this treasure to everyone.

  • Submitted: Jun 14, 2015
  • Stayed: Nov 2014
  • Source: HomeAway
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Beautiful Property, Beautiful Location

  • 5 of 5

I've had the chance to visit the Winthrop Estate in both the winter and the summer, and deeply wish I could see it in the spring and fall as well. The house is beautiful and the rooms are well appointed. The location is ideal -- walking distance to "downtown" Lenox, yet secluded and peaceful. Its a wonderful place to relax or to enjoy quality time with friends.

  • Submitted: Jun 3, 2015
  • Stayed: Dec 2014
  • Source: HomeAway
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Winthrop Estate, spectacular place, great location

  • 5 of 5

We have stayed at the Winthrop Estate twice over the last couple of years. First of all the Lenox area is beautiful, and worthy of lots of exploration. Really, it’s very nice at any time of the year, but in the summer and fall the area is especially gorgeous. And the town itself is a terrific place to shop, eat, or just have a glass of wine and relax in one of the many excellent establishments. But the property of the Estate is wonderful, from the gardens to the views to the lovely porch. Each bedroom has a different style, and we have stayed in the same room each time, it’s our favorite. The views from the second floor are really nice, and the bathroom, while somewhat modernized, still has the tradition original fixtures, and it does make you feel like you are stepping back in time. A special thanks to Jamie, she is very attentive and took great care to make sure our visit was happy. We look forward to our next stay

  • Submitted: May 30, 2015
  • Stayed: Nov 2014
  • Source: HomeAway
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Absolutely lovely

  • 5 of 5

We have stayed here on several occasions and I highly recommend it. The rooms are comfortable, quiet, and beautifully appointed. The lawn and surrounding lands call out to be explored and the town is filled with great restaurants, yoga, and shopping. I look forward to visiting every year in every season!

  • Submitted: May 28, 2015
  • Stayed: May 2015
  • Source: HomeAway
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Absolutely lovely

  • 5 of 5

My family has stayed here on several occasions. It has always been a first rate experience. The rooms are comfortable, beautifully appointed, and quiet. The lawn and surrounding grounds call out to be explored and enjoyed. The town is filled with restaurants, yoga, and shopping. I highly recommend it!

  • Submitted: May 28, 2015
  • Stayed: May 2015
  • Source: HomeAway
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Unique on the American East Coast/New England

  • 5 of 5

My wife, nine-year-old son and I stayed there over Memorial Day weekend. Our imagination soared back to the Gilded age, the 40 acre property is like Nottingham Forest, the five minute walk to town lead to nationally-rated restaurants, interesting shops, and a boutique Tavern scene. The rooms are grand and sunny, the appointments are luxurious, and the owners (world class travelers and well connected in town) provided us with just the right amount conversation and context. And their teenage son tapped the property's trees and made the maple syrup we lavished on our breakfasts. (We even took some home!)

  • Submitted: May 27, 2015
  • Stayed: May 2015
  • Source: HomeAway
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Nearest Airport
70 Miles
Albany, Hartford
Nearest Barpub
0.5 Miles
Brava Bar
Nearest Golf
4 Miles
Cranwell Resort, Spa and Golf Club
Nearest Train
52 Miles
Wassaic Train Station, Metro North
Nearest Motorway
7 Miles
Massachusetts Turnpike, Exit 2
Nearest Restaurant
1 Miles
Nearest Ski
5 Miles
Butternut, Jiminy Peak, Bosquet
Car: recommended

Historic Lenox Village, with restaurants, shops and art galleries is a ten minute walk away (about a half mile). Tanglewood, the summer home of the Boston Symphony Orchestra, James Taylor, Train, and many other performers between June and September is less than a five minute drive, as is Kripalu Yoga Center. The Clark Art Museum, Jacob’s Pillow Dance Festival, Hancock Shaker Village, Shakespeare and Company and the Norman Rockwell museum are also easily accessible. The rolling hills and lush greenery of the Berkshires create wonderful biking, hiking and outdoor activities in all seasons.

Other Activities: Tanglewood, Shakespeare & Co., Clark Art, Jacob's Pillow, Rockwell Museum, Theater Festivals, Hancock Shaker Village, Botanical Gardens, Mansions


Rates & Availability

Lenox Estate Rental Rates

Rental Basis:
per property
Manager accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate
3 night minimum stay

Additional information about rental rates

Cleaning $0
Refundable damage deposit $5,000

50% of the payment is required to reserve your stay - which is refundable if we are able to find replacement renters. The remaining 50% is due 30 days in advance of your stay.

The $5,000 security deposit should be pre-authorized via credit card and will be fully refunded pending a satisfactory inspection of the property after your stay.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Enter dates for accurate pricing
Calendar not updated in over 2 months and may not be available. Look for rentals with Request to Book or updated calendars.

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