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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Beautiful, Private Estate w/ pool, pond, gym, barn etc. Create special memories!

Bedrooms 8
Space 12,000 sq. ft.
Property type estate
Minimum Stay 1 - 7 nights


About the property

6-8 Bedrooms, 5 Full Bathrooms, Sleeps 12-16

Now available for short term rentals or long term leases. Great for all seasons, families, friends or special events!

The Berkshire Country Estate is located on 60 acres in the foothills of the Berkshires within equal distance to the Hudson Valley. It is a large elegant, yet comfortable family Georgian estate with five fireplaces.

Amenities include a gym, pinball, table tennis, air hockey, pool, pond, miles of walking and riding trails, library etc.

If desired, indulge in an ultimate culinary experience and enjoy gourmet dinners of your choice prepared by personal chef. Children's menus available too.

We also have a 4,500 square foot barn on the property, which offers a great additional space to hang out, and for events.

Enjoy year round vacations on your 60 acre estate situated in Old Chatham on miles of riding/hiking trails...12,000 sq ft brick Georgian home with in ground pool, ponds, 6 bedrooms, two double room suites can convert to 8 total bedrooms... 5 baths, 5 fireplaces, library, maid/nanny quarters, finished attic which can sleep six or more kids easily…pinball, air hockey, volleyball, basketball, 3 story barn with ping pong, darts, canoe.... picnic by the pond…

We're here to make your stay extra special! We can stock your refrigerator, cater dinner parties, organize your wedding or special event, arrange for pick ups at the train station, get advance tickets for the many events in and around the Berkshires, set up massages and spa time...

Also, great for special events, weddings, birthdays etc with professional caterers and full event planning available, we'll work with you to design your 'perfect memories'.

Grounds and lawn care, pool maintenance.

Outdoor Activities all year:: Surrounded by rolling fields, manicured lawns, forest & farmland make up your estate. Pitch and putt from your front door on to the 10+ acres of manicured rolling lawns... BBQ and picnic on your brick inlaid patios next to your in ground L shaped pool with mature perennial garden. Relax in the shade of your screened in porch..Hike or ride on the miles of Hunt Club trails surrounding and winding through your estate. Professional Indoor tennis facility less than 1/2 mile down the road. Several fine golf courses or drop your canoe in several lakes and fast running rivers all just minutes away. In the winter Ski Jiminy Peak, Bousquet, Catamount all within 25 minutes or less also abundant Cross country ski trails too...

Culture Vultures & Pamper Too!: The Berkshires is a unique cultural much to see and do...

Tanglewood (summer home of the Boston Symphony Orchestra), Shakespeare & Co., Berkshire Theatre Festival...see the worlds finest dance troupes at Jacobs PIllow...and let's not forget Canyon Ranch, Kirpalu Yoga Center and the Cranwell Golf & Spa Center....all minutes away

Special Events... Create a perfect weekend for that special event whether its a wedding, birthday anniversary etc...Affiliated with the estate are professional caterers, great chefs and party planners...Events within the house or extended to a white tent affair. Inquire and let us help you build a Special Memory...

More Details

Laurie Sherman Graff
Member since: 2011
Speaks: english, italian
Response time:
Within an hour
Response rate:
Calendar last updated:
January 19, 2018

What makes this estate unique

Private, luxury, yet family friendly estate, the Berkshire Country Estate is a great destination, whether you are looking for cultural activities, hiking /nature experiences or just great "chill" time with family and friends.

The estate is located on 60 acres with a 10 acre front lawn and 1/8 mile driveway set far back from the country road.

You can relax in the beautiful in ground pool with no neighbors in sight, hike on the miles of trails, hang out in the 4500 square foot party barn for late night ping pong, foosball or dart additional entertainment level in the main house offers pinball, air hockey, indoor gym or movies. Shoot basketball or play volleyball, playset for the kids...or just relax in the hammock while listening to the sounds of nature. Feed the fish and bullfrogs in the pond. In winter, there are the 5 nearby ski resorts, ice skating and snowshoeing. Enjoy this year round camp for all ages and if you want to leave "campus", there's excellent restaurants, art galleries, antiques, theater, dance performances, museums and more!

So much to do in the area, and if you can find the time, it's a short trip to Saratoga Springs or Cooperstown. We guarantee you won't be bored unless you want to be, and in that case, we'll provide the wine and hammock. Enjoy!!!


Old Chatham Estate Accommodation and Amenities

Property Type:
  • estate
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Optional
Floor Area:
  • 12000 sq. ft.
House Rules:
  • Check-in: Flexible
  • /
  • Check-out: Flexible
  • Max. occupancy: 16
  • Min. age of primary renter: 30
  • Parties/events allowed ...
  • Pets not allowed ...
  • Non smoking only ...
  • Al guests at the Berkshire Country Estate must review and sign our rental agreement, which offers additional information about the estate.
Location Type:
  • Mountain
  • Mountain View
  • Rural
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Alarm System
  • Broadband Access
  • Clothes Dryer ...
  • Fireplace
  • Firewood
  • Fitness Room / Equipment ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Local Maps
  • Local Restaurant Guide
  • Parking ...
  • Security System
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet ...
  • Wood Fireplace ...
  • 4 Ring Stove
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Kitchen
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 8 people
  • 5 Bathrooms
  • Bathroom 3 - toilet , shower , bidet
    Bathroom 4 - toilet , shower
    Bathroom 5 - toilet , shower
    Bathroom 1 - toilet , shower , jetted tub , bidet , Over-sized Jacuzzi tub in spacious master bathroom
    Bathroom 2 - toilet , tub , shower , bidet , Oversized deep soak tub in spacious master bathroom
  • 8 Bedrooms, Sleeps 16
  • Bedroom 8 - 1 sleep sofa /futon
    Bedroom 1 - 1 king , Fireplace/sitting room
    Bedroom 4 - 1 double
    Bedroom 3 - 1 double , sitting area,private entrance
    Bedroom 5 - 1 queen
    Bedroom 6 - 1 queen
    Bedroom 7 - 1 queen , 2 twin/ single
    Bedroom 2 - 1 queen , Fireplace/sitting room/library
  • 5 master bedrooms 3 ensuite with separate sitting rooms, fireplaces, soak & jacuzzi tubs, beautifully furnished, yet comfortable and spacious
  • Air Hockey
  • Books ...
  • Books for Adults
  • Books for Kids
  • CD Player
  • DVD Player
  • Foosball
  • Game Room ...
  • Games ...
  • Games for Kids
  • Music Library
  • Ping Pong Table
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • Toys ...
  • Video Library
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Binoculars
  • Child's Swing
  • Deck / Patio
  • Golf ...
  • Golf Clubs
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill
  • Patio
  • Porch / Veranda ...
  • Raft
  • Sand Box
  • Screen Porch / Veranda
  • Ski & Snowboard ...
  • Small Cooler
  • Tennis ...
  • Long-term Renters Welcome
Pool / Spa:
  • Heated Pool
  • In Ground Pool
  • Jacuzzi
  • Outdoor Pool
  • Private Pool
  • jetted tub
Onsite Services:
  • Massage
  • Private Chef
  • arboretum
  • autumn foliage
  • botanical garden
  • caves
  • churches
  • cinemas
  • festivals
  • forests
  • library
  • live theater
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • synagogues
  • water parks
  • waterfalls
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • 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
  • rafting
  • sailing
  • ski privileges optional
  • skiing
  • swimming
  • tennis
  • water skiing
  • water tubing
Great privacy for 3 couple share....Wonderful for larger families, friend/family reunions, special celebrations such as birthdays, anniversaries, weddings etc. A party barn too!


Wonderful! 4.8/5 -
(29 traveler reviews)

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Beautiful, Private Estate w/ pool, pond, gym, barn etc. Create special memories!
average rating of 4.793103 based on 29 reviews

The perfect getaway for our wedding

  • 5 of 5

We rented the estate for our wedding. We wanted our event to have the feel of a back-yard family party and we wanted to encourage our family and wedding party members to actually take a few days off. Staying at the estate for the week allowed us exactly that.

As a host, Laurie was an excellent resource for local vendors and was spectacularly warm. The house is stunning and comfortable providing the perfect blend of environment of rest and relaxation while also providing incredible decor for photo backdrops.

My family is already talking about scheduling regular vacations at the estate, and we can't wait to revisit a place that now holds such incredible significance.

  • Submitted: Aug 22, 2017
  • Stayed: June 2017
  • Source: HomeAway
Owner's Response: Dear Dante and John, Thank you so much for the nice review! It gives me great pleasure to have played a small part in creating a very special memory for you and yours. You were wonderful guests, and we very much look forward to hosting you again at the Berkshire Country Estate! Many thanks & warmest wishes, Laurie
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Wonderful 4-generation vacation

  • 5 of 5

We had a relaxing, fun vacation in this beautiful, spacious home. There was plenty of room for us, 12 adults and a toddler. Laurie made our stay so easy and pleasant, from making the reservation through checking out. We had everything we needed. We especially loved the pool and enclosed porch. There are even pool toys! We mostly stayed on the property, swimming, playing ping pong in the barn and air hockey in the basement. Everyone, from the great grandparents to the toddler, was comfortable and had a great time. Thanks so much, Laurie, for sharing your beautiful home with us!

  • Submitted: Aug 13, 2017
  • Stayed: June 2017
  • Source: HomeAway
Owner's Response: Alisa, It was a pleasure hosting you and your family! Please come back soon! You are welcome anytime! Warmest wishes, Laurie
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We really enjoyed our stay!

  • 5 of 5

We had 7 adults + 6 children over the weekend. Each child + couple had their own space to sleep which was a huge factor in making the weekend great. Would stay again!

  • Submitted: May 12, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Julie, Thank you for being such wonderful guests! You are welcome back anytime. Hope that the weather cooperates and you can enjoy the pool, the BBQ and the new rec room items in the barn on your next visit! Warm wishes, Laurie
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As advertised

  • 5 of 5

We had 16 adults stay up at the Berkshire Country Estate this past weekend to celebrate my birthday. The house was in pristine condition with plenty of room to make everyone feel comfortable. With the unusual cold snap, we spent the majority of the weekend indoors at the house and enjoyed the game room, the living room and toasty fires (although the heat in the house was strong and we didn't need it). We also were able to sit in the dining room all at once and enjoy family meals together. We'll totally rent this house again, and will come back in the summer to enjoy the beautiful grounds and the pool!

  • Submitted: Mar 15, 2017
  • Stayed: March 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank YOU for being such great guests! We're so happy that the Berkshire Country Estate was able to create wonderful memories for your special birthday weekend. Looking forward to hosting you & yours again at the Berkshire Country Estate!
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Beautiful house!

  • 5 of 5

Laurie has done an amazing job with the house! We had a large group of family and everyone was comfortable. The barn has some great recreational activities which kept our group busy. The location is also very convenient being midway between the berkshires and the town of Hudson.

  • Submitted: Nov 14, 2016
  • Stayed: November 2016
  • Source: HomeAway
Owner's Response: Thank you for being such great guests! I hope that you will join us again at the Berkshire Country Estate. Warmest wishes, Laurie
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Small Wedding

  • 5 of 5

We stayed at Berkshire in mid July. At the end of the week we had a very small wedding. First of all, the house is fantastic. Everything you possibly could want in a vacation home. It is very clean & well maintained. Laurie was very accommodating. It is obvious she wants you to enjoy the house & the area, as much as she does. Whatever your interests are, Laurie will surely know where to find it & if not she is willing to do the research.

The house is the perfect venue for a wedding. With all the rage for barn weddings, the backdrop is just beautiful. My guests were in awe of the house, the location & the grounds. Being a destination wedding for us, we depended on Laurie for recommendations. Just when you think you thought of it all, Laurie reminds you about something you wouldn't even think about.

I had a more rustic, small, intimate affair. But the grounds are so large & secluded, that it is perfect for any size wedding. You could go all out, rent a large tent for eating & use the barn for dancing. We used the barn for food service, dancing & supplied our own music. If you are looking for something different, you can't go wrong at this beautiful Estate.

  • Submitted: Oct 8, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: We really enjoyed hosting your special day and creating beautiful memories for you and yours at the Berkshire Country Estate! Wishing you both a beautiful life together! Warmest wishes, Laurie
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Nearest Airport
20 Miles
Albany International
Nearest Barpub
6 Miles
Town of Chatham
Nearest Golf
5 Miles
Several quality courses in area
Nearest Train
10 Miles
Hudson Station AmTrak
Nearest Motorway
3 Miles
Taconic State Parkway and US 90
Nearest Restaurant
6 Miles
Town of Chatham
Nearest Ski
12 Miles
Bousquet or Catamount
Car: necessary

Local Attractions and Activities

Spas: Cranwell in Lenox, Canyon Ranch sometimes allows day passes for locals (you could use our address), Kripalu (Yoga and treatments), Hudson has Bodhi Spa, massage, facials etc

Wineries: Here's two to start...the local Hudson-Chatham Winery offers complimentary wine tastings to all Berkshire Country Estate guests; Hilltop Orchards and Furnace Brook Winery in Richmond, Ma. There is a fireplace at Furnace Brook Winery and you can rent snowshoes to hike through the apple orchard. It’s a wonderful place to just sit by the fire with your glass of wine too! There is also a very cool distillery at Golden Harvest Farm, and Chatham has it's own brewery too!

Theater and Culture: The Berkshires offers many opportunities, and Hudson has some wonderful music venues. As we get closer to your stay, please let me know your interests, and I can offer some referrals.

Golf: If you and yours golf, but there are many very good golf courses in the area, including the Cranwell in Lenox and Copake Lake in Copake, NY. Others are as nearby as a 6 minute drive!

Miles and miles of hiking both in Columbia County and Berkshires. We are located on the Old Chatham Hunt Club Trails, so there are wonderful trails surrounding our property. Located two minutes up our road is a beautiful new site called Ooms Conservancy with a 35 acre pond. Also Queechy Lake in Caanan is a beautiful 140 acre lake with a sandy beach. Cross country and snow shoeing on property.

Restaurants, Antiques and Art Galleries in Hudson on Warren Street: Some of my restaurant faves include American Glory (great BBQ), Mexican Radio, Baba Louies delicious gourmet pizza. In Great Barrington, MA, there is a wonderful Japanese restaurant, Bizen. Also Rouge in West Stockbridge is a culinary destination. Award-winning Farm to Table restaurant in nearby Philmont is Local 111. Blueberry Hill in New Lebanon is great for breakfast

Wonderful berry and fruit picking at many nearby farms throughout Columbia County. June is berry picking season, and Fall is apple picking season! Try the Berry Farm in Chatham, Love Apple Farm in Ghent and Golden Harvest in Valatie.

There are at least 5 nearby ski resorts that offer both winter and summer activities. Bousquet Ski Resort offers summer activities that include six waterslides, an activity pool, zip-line, 9-hole disc golf course, bungy -trampoline, climbing wall, bounce castle and Adventure Park ropes course. Catamount Ski Resort offers an aeriel adventure park with over 50 zip lines and 12 separate courses. Jiminy Peak Ski Resort additional activities include the Mountain Adventure Park, which has the alpine super slide, mountain coaster, hiking, and mountain biking.

So much to do both ... 20 Minutes to Lenox MA and all the cultural attractions of the Berkshires including; Tangelwood(summer home of the Boston Symphony Orchestra), Shakespeare & Co., Berkshire Theatre Festival, Jacobs Pillow Dance Center

etc...and 15-20 minutes to the Hudson River and all the Hudson River Valley has to offer! We are also close to Saratoga Springs, Cooperstown, Troy, Williamstown and Howes Caverns for day trips:)


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $275
Linen Fee $35
Property Damage Protection $59
Refundable damage deposit $1,500

Peak holiday stays will incur an additional rental rate.
Property manager or owner requires a phone call with all prospective guests prior to approving a booking for the Berkshire Country Estate. Please call (646) 761-7612. We need the full names of all guests who will be staying at the property. Additional day guests or events without the prior consent of the property owner are not permitted. Berkshire Country Estate has a standard rental agreement with additional details about the property which all guests must review and sign prior to check in. Thank you!

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.