check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag

Ferry Tix, Chilmark, South of South Rd, 4Bd/4Bth, Central Air, Pet Friendly Wifi

12 Reviews
Bedrooms 4
Property type estate
Minimum Stay 2 - 7 nights

Pay with confidence

When you book through the HomeAway checkout, your booking is backed by our Book with Confidence Guarantee™ offering comprehensive payment protection.

Learn more


Minimum Stay
2 - 7 nights


Chilmark Estate Rental Photos and Description

Elegant, Authentic Arts & Crafts Estate, Gourmet Kitchen, Unequaled Views

Architect designed 4 Bd/4 Bth + detached studio, 360 degree wraparound veranda, tastefully furnished and appointed, exquisitely detailed. Stunning views across open expansive meadows. Separate guest house (2 Bed/1 Bath + Loft) available. See the series of photos capturing the compound. The first series of pictures are of the Main House (exterior, interior + detached studio). Together, the Main + Studio offers 4 bedrooms, 4 bathrooms. Each bathroom features decorator tile, Grohe fixtures and high-end finishes.

The second set of photos show the Guest House, which has a separate entrance as well as pea-gravel driveway with ample parking. It is very private, serene and set off a good distance from the Main House so that you would not feel the properties are connected.

The property can be rented either as a compound or as separate homes. As a compound, it would work great for family reunions, extended families or folks who simply like to entertain whilst on holiday.

Gray Oaks was built in 2004 by world-renowned architect Michael Ball. The homes now feature central air-conditioning and have been freshly painted inside and out. The three homes come complete with all new high-end appliances, professional landscaping, Arroyo craftsman lighting fixtures + Stickley furnishings. In addition, phantom screens have been added to all french doors (3 sets) as well as to the back entrance. I must say the property was well-sited by Michael Ball and is cool no matter what the temperature outside.

A great new feature added to the property are the cobblestone walkways built by local artisans from real river stones which lead from the roads to the entryways. They are spectacular, providing both charm and function. Additionally, the roads have all been properly constructed with the estate-worthy driveways being covered in highly-desirable pea gravel.

Gray Oaks is south of South Road. It is the first left off of Quansoo Road. It is terribly convenient (yet private) as you are centrally located to the beaches, shops and Alley's, yet will never be trapped in vacation traffic. Our family often bikes to private beaches (Quansoo, Black Point) in less than 15 minutes. The property is also surrounded by countless walking trails and ancient ways. Each house has LL Bean hammocks, fireplaces and the Main House offers a fantastic, competition ping-pong table!

The property is elegant and an architectural masterpiece of the Craftsman style. The Main (including the detached studio) offers 4 bedrooms and 4 bathrooms. There is a 360 degree wraparound veranda, gourmet kitchen, Weber grills and is tastefully furnished, exquisitely detailed with unequated sunset views across open, expansive meadows. Gray Oaks abuts Gray Barn, which is 69+ acres of conservation land, an organic gentleman's arm. Gray Oaks is quite a magical spot with what I believe to be the best lighting to be found on Martha's Vineyard.

More Details
  • Events Allowed
  • Long-term Renters Welcome
  • children welcome
  • non smoking only
  • pets considered
  • wheelchair inaccessible

Member since: 2014
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
October 10, 2016
Call Owner

About Linda

When visiting Martha's Vineyard don't miss Chilmark's world-renowned private south shore beaches! About me? I began coming to MV as a child more than 40 years ago and today cherish the memories of time spent riding the waves, catching blue crabs and building sand castles with my late parents. In 1990, we bought our first tiny bungalow in Edgartown and gradually worked our way up to buying our dream home, Gray Oaks in 2012! Our family compound has allowed us to host a fantastic family reunion, house friends from England and New York City for summer weeks of fun and sun! Entertaining here is easy and breezy. The homes are elegant, tastefully furnished and appointed, with unequaled sunset views across open expansive meadows.

Linda purchased this estate in 2012

Why Linda chose Martha's Vineyard

I am privileged to provide wonderful accommodations for folks to enjoy one of the most beautiful places on Earth!

What makes this estate unique

This property is elegant and an architectural masterpiece of the Craftsman style. Gray Oaks abuts Gray Barn which is 69+ acres of conservation land, and is now an organic gentleman's farm. Gray Oaks offers some of the most magic light on Martha's Vineyard. It is a fantastic spot with easy access to all, especially Chilmark's world-class south shore beaches!


based on 12 traveler reviews

Ferry Tix, Chilmark, South of South Rd, 4Bd/4Bth, Central Air, Pet Friendly Wifi
average rating of 4.9166665 based on 12 reviews

What a wonderful week! My family looks forward to returning to Gray Oaks!

  • 5 of 5

This lovely home is as advertised -- comfortable, clean, air-conditioned (a rarity on Martha's Vineyard) and completely "away from it all." We were welcomed by blooming perennials and lovely potted plants -- as well as cows mooing in the distance. Inside, we found the house to be spacious and well-appointed. Our only regret is we could not stay longer.

  • Submitted: Aug 8, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Lovely summer home in a serene setting

  • 5 of 5

We loved our week in Gray Oaks and found that we much preferred the Chilmark location over other properties we've rented in the busy parts of the island near Edgartown and Oak Bluffs. The house is lovely and extremely comfortable -- within hours we had settled in and felt as if we'd been there for months. The wrap around porch is fabulous and made for extremely enjoyable morning coffees, evening cocktails, and afternoon naps! As described on the website, the light on the property is gorgeous especially in early morning and evening. The occasional moo from the nearby Grey Barn farm only heightened the pastoral setting.

The location is fantastic if you want to experience the island from a more local perspective and very near some of the most quintessential island experiences: great beaches like Lucy Vincent, Philbin, Aquinnah and Menemsha; foodshops like Larsons Fish Market, Chilmark General Store, Grey Barn cheeses,Homeport restaurant and West Tisbury Farmers Market; and sights like the Aquinnah lighthouse or Menemsha fishing docks. The airport is only a few minutes away as is the drive to Vineyard Haven, Oak Bluffs and Edgartown.

Working with Linda, the owner, was a pleasure. She was extremely responsive and concerned about our overall experience. She responded quickly to any and all questions and provided lots of extra helpful advice. We would happily rent the house again on a future visit.

  • Submitted: Jul 19, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
1 0

Wonderful, peaceful, relaxing week-end. My family and I enjoyed the house as if we were home.

  • 5 of 5

Secluded, well appointed home. Very comfortable, airy, and clean. Grounds are well kept and inviting, wrap around porch makes the island visit special.

  • Submitted: Jun 16, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Beautiful and tranquil.

  • 4 of 5

House is found after going down some bumpy dirt roads, a real feeling of adventure. Owner easy to work with. House beautiful, in very quiet area. Loved seeing the cliffs. Unfortunately we went in April when very few businesses in Martha's Vineyard are open, nothing was in bloom, and it was still very cold. But there was a certain beauty in the stillness. We would plan to go sometime after May 1st if we visit again.

  • Submitted: Apr 27, 2016
  • Stayed: Apr 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

5 Stars. Amazing House and Property

  • 5 of 5

We had such a nice time at Gray Oaks this June. The property was perfect for our our 3 year old son and Springer Spaniel. The house is beautiful with wrap around porch and open floor plan! We loved watching sunsets over the adjoining field in the evening. Highly recommend. Owner is also fabulous to work with! We would love to return next year:)

  • Submitted: Jun 17, 2015
  • Stayed: Jun 2015
  • Source: VRBO, from HomeAway
Did you find this review helpful?
2 0
Boston area

Secluded Vineyard getaway

  • 5 of 5

Spent a wonderful week here. The house, the location, the amenities were all incredible. It's bright, clean, modern (but also very beach-y). Morning coffee on the warp-around porch. Evening ping-pong on the deck. Quick bike ride (or moderate walk) to beautiful beaches. Couldn't have asked for more.

  • Submitted: Nov 13, 2014
  • Stayed: Sep 2014
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0



Rates & Availability

Chilmark Estate Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Sep 18 2016 - Dec 31 2016
2 night minimum stay
Jan 1 2017 - May 24 2017
2 night minimum stay
May 25 2017 - Jun 23 2017
3 night minimum stay
Jun 24 2017 - Jul 21 2017
7 night minimum stay
Jul 22 2017 - Sep 4 2017
7 night minimum stay
Sep 5 2017 - Oct 3 2017
7 night minimum stay

Additional information about rental rates

Refundable damage deposit $1,000
Pet Fee $350
Turnover Fee $350

Rates and Terms are subject to change until rental is confirmed.

Inquire for compound rates.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
Send a Message
Available arrival
Available stay (no arrival)


Chilmark Estate Accommodation and Amenities

Property Type:
  • estate
  • Guests provide their own meals
Floor Area:
  • 2500 sq. ft.
  • Adventure
  • Away From It All
  • Family
  • Air Conditioning
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 4 Bathrooms
  • Bathroom 1 - toilet , shower , Main floor bathroom offers outdoor access, hi-end finishes
    Bathroom 4 - toilet , shower , Detached Studio full bathroom. Clean, nautical.
    Bathroom 2 - toilet , shower , jetted tub , master bath features rain shower head, body jets, luxurious
    Bathroom 3 - toilet , shower , Gorgeous custom bathroom, decorator tile, high-end finishes
  • Outdoor shower access great for family when coming home from gorgeous Chilmark beaches. Custom tile in each bathroom, Grohe fixtures throughout, Craftsman inspired, spacious, clean and lovely.
  • 4 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 king , Stickley furnishings throughout
    Bedroom 2 - 2 child bed , two matching white wrought iron beds. gorgeous ensuite
    Bedroom 3 - 1 queen , Main floor queen with full bathroom.
    Bedroom 4 - 2 sleep sofa /futon , Gorgeous wicker day bed, extra long + trundle twin
  • Three bedrooms, three baths in Main House + gorgeous detached Studio which sleeps 2, full bathroom and kitchenette.
  • DVD Player
  • Ping Pong Table
  • Satellite / Cable
  • Television ...
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill ...
  • Events Allowed
  • Long-term Renters Welcome
  • children welcome
  • non smoking only
  • pets considered ...
  • wheelchair inaccessible

Partner Offers