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Utopia w/ Pool, Tennis, Playfort, Trampoline, Tree Swings, Laying Hens, Bonfires

Bedrooms 5
Half Baths1
Space 3,400 sq ft
Property type farmhouse
Minimum Stay 0 - 2 nights


About the property

Ideal Family Farmhouse on 35 acres w/ 5 Bedrooms, 2.5 Bathrooms, Sleeps up to 13

Calling All Foodies And Nature Lovers To The Farmhouse At Craryville - A Victorian Wonderland With Bohemian Flair Set on A 35-Acre Rural Estate. Nestled In The Foothills Of The Berkshires, At The Crossroads Of New York And Massachusetts, Our Farm Estate Is The Ideal Country Getaway For A Gathering Of Family and Friends! Located At The Crossroads Of The Bucolic Upstate New York And The Berkshires, This Victorian-Era Farmhouse Is The Perfect Holiday Escape.

The Period Home Retains It's Historical Character With Original Wide Board Floors, Decorative Woodwork, And Objects Of Curiosity Throughout. The Modern Eat-in Kitchen Is Equipped With A Gas Cooktop And Oven By Bosch, A Miele Dishwasher, Large Capacity Amana Refrigerator, A Kenmore Front-loading Washer And Dryer. Upstairs, Five Sleeping Quarters Accommodate Thirteen Guests Comfortably, With A California King Room, A Queen-sized Room, A Room With Two Twin Beds, A Media Room With A Convertible King Bed or Two Twins, And A Room With Two Bunk Beds And A Twin Trundle, Plus Two Full Bathrooms. Downstairs, A Lovely Light-Filled Sitting Room And Library With A Wood-burning Fireplace, Overlooking A Bucolic 300-acre Organic Farm , And A Separate Dining Space With Its Own Wood-burning Fireplace And Powder Room Round Out The First Level Of The House. Weber Grills Live Outside The Kitchen Door for Year-round Alfresco Cooking.

Outdoor Wonderland Includes: Bonfire Ring; Huge 20 ft. x 40 ft. Heated Swimming Pool; Hardscape Tennis Court With Sweeping Views Of The Mountains; 15 ft. Wide Trampoline, Kid's Play Fort With Viking Ship Climbing Structure And Tree Swings; Chicken Coop With 7 Laying Hens! Many acres of Grass, Flowering Meadow and Forest to Explore. Hudson is just 20 minutes directly west and Great Barrington is just 20 minutes due East. And our Hamlet of Hillsdale has its own Saturday Farmer's Market and great local shops to explore. Summer Perfection!

More Details

Vanessa Dawson
Member since: 2015
Speaks english
Response time:
Within a few hours
Response rate:
Calendar last updated:
April 10, 2018

About Vanessa Dawson

I'm an appreciator of good architecture and interior design who makes a living doing adaptive reuse of interesting historic structures. Before buying this property, my screenwriter husband and I redeveloped a blown-out old Brooklyn dairy carriage house into three modern homes on the border of Park Slope and Gowanus. We bought this dreamy spread to let our boys run wild.

We raise chickens, try to grow some food, and have learned a bit about the wild edibles native to this beautiful place. We are happy to share this experience with other families looking for privacy, some luxury, and all the childlike wonders of the natural world.

Vanessa Dawson purchased this farmhouse in 2012

Guestbook comments from the owner

We have had a wonderful time here. We have a specially enjoyed the fire pit. I might add as we are all cooks that we really were grateful for the excellent sharp knives in your very nice kitchen and took good care of them. Ron read a number of books in the library and was happy to find some Elmore Leonard he had not previously read and we all love the dog book.
Jul 2016
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Accommodation and Amenities for this vacation farmhouse rental in Hillsdale, New York

Property Type:
  • farmhouse
  • Guests provide their own meals
Floor Area:
  • 3400 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 13
  • Max. adults: 8
  • Min. age of primary renter: 34
  • Children welcome
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only ...
Location Type:
  • Mountain View
  • Rural
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer ...
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Linens Provided ...
  • Living Room ...
  • Parking
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Room
  • seating for 13 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower , clawfoot tub with shower
    Bathroom 2 - toilet , shower , This bathroom is in the Queen bedroom
    Bathroom 3 - toilet
  • Two Full Baths and One Powder Room
  • 5 Bedrooms, Sleeps 13
  • Bedroom 2 - 1 queen
    Bedroom 1 - 1 king
    Bedroom 5 - 2 twin/ single , two twin beds
    Bedroom 3 - 1 king , Media Room w/Trundle bed can be made up as 2 twins or 1 king
    Bedroom 4 - 1 twin/ single , 2 bunk bed , Two Bunk Beds plus a twin trundle bed
  • Books
  • DVD Player
  • Games ...
  • Television ...
  • Toys ...
  • Video Library
  • Deck / Patio ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Ski & Snowboard ...
  • Tennis ...
  • wheelchair inaccessible
Pool / Spa:
  • Private Pool ...
  • arboretum
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • museums
  • playground
  • restaurants
  • synagogues
  • theme parks
  • water parks
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • miniature golf
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cross country skiing
  • cycling
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • ice skating
  • kayaking
  • mountain biking
  • mountain climbing
  • mountaineering
  • paragliding
  • rafting
  • rock climbing
  • sailing
  • skiing
  • snowboarding
  • snowmobiling
  • swimming
  • tennis
  • water skiing
  • water tubing
  • whitewater rafting


Exceptional! 5/5 -
(7 traveler reviews)

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Utopia w/ Pool, Tennis, Playfort, Trampoline, Tree Swings, Laying Hens, Bonfires
average rating of 5.0 based on 11 reviews
Brooklyn, NY

Beautiful home in a peaceful setting.

  • 5 of 5

Having rented multiple homes in the Hillsdale area, I can easily say this was one of the nicest of the bunch. The house is big and well laid out; with great communal spaces but also several little "nooks" if you're looking for to have quiet time. The kitchen is great for cooking; large and well-stocked. Would definitely return in the warmer months to enjoy the pool and tennis courts!

  • Submitted: 2-Jan-2018
  • Stayed: December 2017
  • Source: HomeAway
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Beautiful property

  • 5 of 5

I would have given it 4.5 stars, but between having to choose 4 and 5, decided to give it a 5. The main reason was the owner, as others have mentioned Vanessa is great to deal with and very accommodating. And the only reason i was thinking 4.5 instead of 5 was because of the lack of air conditioning. Other wise the property is amazing!

  • Submitted: 10-Sep-2015
  • Stayed: August 2015
  • Source: VRBO, from HomeAway
Owner's Response: The house has been updated with A/C in all of the bedrooms. Thank you for the feedback!
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Brooklyn, New York

Amazing weekend away

  • 5 of 5

We stayed at this house with a few old friends and all our kids. The house and property are as beautiful as in the pictures. The bedrooms are comfortable (one night was a little hot with the fans), the kitchen has everything you need. The sitting rooms are charming and beautiful, however were barely used since we were outside all day! The pool is stunning, huge and the perfect temperature. The kids had a blast in the play house, canoe and just running around on all the grass!! Vanessa is great to deal with.

Will definitely be back.

  • Submitted: 2-Sep-2015
  • Stayed: August 2015
  • Source: VRBO, from HomeAway
Owner's Response: The house has been updated with air conditioning in all of the bedrooms. Thank you for the feedback!
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Country House Perfection

  • 5 of 5

This farmhouse is a truly special place and provides everything you could dream of in a country retreat. The house itself is beautiful -- the epitome of rustic luxury. Modern kitchen and bathrooms, a large dining room and living room to accommodate larger groups, and a cozy library and stylish bedrooms for those seeking privacy or a quiet room to read. Outside is even better with a gorgeous pool, tennis courts, fire pit, grill, chickens (laying eggs you can eat) and a fresh herb and vegetable garden. The house has everything you could possibly want. But even though you feel like you are miles away from everything, you are a short twenty minutes from the charming town of Hudson and its quaint antique shops and farm to table restaurants. Our host even went the extra mile to make us feel at home by leaving us the most delicious homemade granola we have ever tasted and lovely locally made soaps. We loved everything about our stay and can't wait to go back.

  • Submitted: 7-Jul-2015
  • Stayed: July 2015
  • Source: VRBO, from HomeAway
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It's the kind of home that makes you want to move to the country.

  • 5 of 5

We loved our stay so much. The home is an enviable example of every New Yorker’s dream upstate house. Though its minimal design is evocative of a Dwell magazine spread, it in no way sacrifices comfort to achieve that feeling. The breakfast nook is perfect for long breakfasts reading the paper and drinking coffee. We loved sitting around the fire pit, from which you have a perfect view of the verdant lawn and flower beds. The pool is surrounded with so much greenery that you’ll feel a million miles away from the stress of the city. I never wanted to leave. Do yourself a favor and book it now.

  • Submitted: 20-Jun-2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
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Found my dreamhome in Hillsdale, NY!

  • 5 of 5

This house!!! Where to begin?! Stunningly beautiful, impeccably maintained, cool modern furnishings, warm, charming, stylish, spacious. Lots of ooohs and ahhs from the adults and our kids were in heaven rotating from pool to tree swings to tennis courts to chicken coop then back to the pool. And tons of pretty land for exploring. We loved the designer kitchen and made great use of the BBQ, nothing better than eating shish kebabs and s'mores around a bon fire after lounging by the pool all day. Also loved the location, within 20-30 minutes to several lovely towns, Great Barrington (go to Prarie Whale), Hudson (Spotty Dog books and Ale) and Chatham (Chatham Brewery) although there is really no reason to ever leave the house. This vacation rental gets my highest rating, I cannot wait to return!

  • Submitted: 19-Jun-2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
55 Miles
Albany International
Nearest Barpub
3 Miles
Copake Country Club, The Mill
Nearest Golf
3 Miles
Copake County Club
Nearest Train
15 Miles
Hudson Amtrak, Wassaic Metro North
Nearest Restaurant
4 Miles
Crossroads Food Shop
Nearest Ski
7 Miles
Catamount Ski Area, Butternut Ski Area
Nearest Beach
15 Miles
Lake Taconic;Lake Mansfield;Green River Swim Holes
Car: necessary

pick your own organic strawberries at blueberries at Thompson Finch Farm

Hiking to magnificent waterfalls at Bash Bish Falls

Biking on the Harlem River Rail Trail

Eco tours and classes at Hawthorne Valley Farm

Bard Summer Stage

Hudson Opera House

Live Music Performances at Helsinki and Basilica Hudson

Great Barrington Film Festival

Jug End Reservation


Rates & Availability

Rental Rates for this vacation farmhouse rental in Hillsdale, New York

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Jun 8 2018 - Sep 4 2018
2 night minimum stay

Additional information about rental rates

Housekeeping C$385.32
Refundable Damage Deposit C$2,568.8

Please note that holiday periods are subject to a higher rate. Please inquire with Owner.
Rates are subject to change until reservation is confirmed. Owner reserves the right to cancel the reservation with a full refund. Guests will be required to execute a short terms rental agreement in order to confirm a reservation.

Owner's Cancellation Policy

  • No refunds for cancellations made after payment is made
Contact Owner