Virtual Tour
USA Massachusetts Martha's Vineyard Oak Bluffs Listing #23705

The Oak Estate - Oak Bluffs, MA

6 reviews
Max occupancy: 8 3 Queen Bed, 2 Twin Bed 4 bedrooms 3 bathrooms No pets 
65 Winemack St, Oak Bluffs, MA 02557

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.

Family friendly home w/ ocean views, pool table, full kitchen, & gas fireplace

This spectacular home features almost 4,000 square feet of living space. Located in East Chop, this house boasts views of Crystal Lake and the Vineyard Sound from all three floors. Recent decorative touches include a tiled backsplash in the kitchen, a warming gas fireplace with a mantle in the living room, and an outdoor shower.

What's nearby:
Take a short drive east into downtown Oak Bluffs or west across the water to Vineyard Haven for amazing restaurants and cute local shops. Visit the historic East Chop Lighthouse, less than a mile from your home. And don't miss the various local beaches scattered around the island for fun days in the sun.

Things to know:
Full kitchen with a dishwasher
Outdoor shower 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.

Property tax ID: C0147892210



Children's games


Washer/dryer : Private

Heating & cooling

Central AC


Gas fireplace

Kitchen & dining






Water view




On-site activities

Pool table : Private





Enclosed yard

6 reviews

Piyar D. Mar 2020
The home was spacious and well appointed. The kitchen had every gadget we needed for preparing apps and cocktails. The living room was spacious with comfortable seating. WiFi is always a necessity and it was fast. Heating was zoned so we were never too warm or too cold. The bedrooms are on the first floor and actually a convenience when it comes to hauling luggage in and out. I definitely plan to come back. Highly recommend this home.
Timothy W. Jan 2020
House was clean and comfortable. One small problem with hot water and could not fix it on New Year’s Day, understandable. However company stood by the problem and was fair with us. Totally recommend this property and Vacasa.
Kathleen B. Sep 2019
This property was everything you would want in a vacation getaway on Martha's Vineyard - quiet tree lined street, 3 porches including a fabulous water view, 3 levels of beautiful, immaculate, well-equipped living space! I've been wanting to stay in East Chop, and I could not have been happier! If you have a car, Circuit Avenue is a 5 minute drive, and Seaview Avenue is 6 minutes. If you don't have a car, the house is a five minute walk from the bus stop and located almost exactly as close to Vineyard Haven. I hope to rent it again for my next visit.
HOLLY L. Aug 2019
We loved the house, very spacious & great location
Roberta W. Aug 2019
Lovely home with large gathering spaces, dining room and a kitchen with island. Pool room has a counter fridge and sink. 3 full Bathrooms on each level very nice for the Vineyard. Would definitely stay again!
Colleen S. Jul 2019
Great location nice neighborhood! Perfect for morning runs, family visits, and short walk to OB center.