Virtual Tour
USA Massachusetts Martha's Vineyard Chilmark Listing #28942

Hillside Oak - Chilmark, MA

2 reviews
Max occupancy: 8 2 Queen Bed, 2 Double Bed 4 bedrooms 4 bathrooms 4 dog max 
81 Gosnold's Way, Chilmark, MA 02535

Worry-free booking

Enjoy peace of mind with flexible options to change or cancel your trip.

If your check-in date is at least 30 days away, you can reschedule your trip, cancel and receive 100% of the cost as a Future Stay Credit, or cancel for a refund (minus the booking fee).

Expert cleaning

Professional housekeepers clean and stock each home, using an EPA-approved disinfectant.

Local support

Each trip is backed by 24/7 customer support and local teams everywhere we operate.


Many Vacasa homes use smart locks or lockboxes for a smooth, contactless check-in.

Private Hillside Home with Open Property and a Fully Equipped Kitchen

This gorgeous 4 bedroom home is set back in the oaky forest of Chillmark. The scenic drive down the hillside to this home provides some of the greatest views on Marthas Vineyard, overlooking the ocean and surrounding island. Upon arrival to the property the woods open up to a colonial style home with a clean lawn on the hillsides of Chillmark. Inside the home, you will find all the historic charm the Cape and Islands are known for. The numerous amounts of windows make you feel like you are truly tucked away in your own world in the forest. This home sports an open concept that provides an optimal area for entertaining friends and family.

What's Nearby?
1 mile to north shore beach
4 Miles to Lucy Vincent Beach
15 miles from Vineyard Haven ferry dock
17 miles from Oak Bluffs
9 miles from Marthas Vineyard Airport
Menemshma Hills Walking Trails are less than 1/4 mile away

Things to Know:
Full Kitchen
Please note: This home is fully winterized and the current photos do not show the 4th bedroom with 2nd double bed A damage waiver, covering up to $2,000 of accidental damage to the property or its contents, is included in the cost of your reservation.

You must be 21 years or older to rent this property.



Children's games


Washer/dryer : Private

Heating & cooling


Wood stove

Kitchen & dining






Internet : Verizon Wireless



DVD library

DVD player

VHS library

Wireless router


Nearby activities & attractions

Golf Nearby

On-site activities

Board games



Beach towels


2 reviews

Spencer S. Aug 2020
Loved everything about this house - great location and accommodating property owner.
Chitrang P. Jul 2020
Our family loved the house and will plan to go back. The location is great too.