PRIVATE CHAPPY WATERFRONT-360o WATERVIEWS/SAILBOATS, KAYAKS, PADDLEBOARDS

The Outermost House | Private Waterfront Family Compound – Chappaquiddick that sleeps 14 guests. Some SSA tickets available. Fantastic REVIEWS available upon requests!! Book early for 10% discounts.
And play golf at the nearby 9 hole course of Royal and Ancient Chappy links. https://www.royalchappy.com/


Accommodations

The main house offers four large bedrooms, each with its own en-suite bath and shower. The primary suite features a full-size soaking tub for post-beach relaxation. At the heart of the home is a chef-approved gourmet kitchen, ideal for family meals, catered lobster bakes, and entertaining.

A separate guest cottage provides additional privacy and is especially popular with children and teens. It includes four bunk beds, a queen-size bed, an outdoor shower, and a very large deck with fire pit—perfect for evening ghost stories and stargazing.

A Rare, Secluded Vineyard Setting -minutes from Edgartown

Create an unforgettable family reunion or multigenerational summer retreat at The Outermost House, a private compound on Chappaquiddick Island—featured in Boston Common magazine for its complete seclusion and extraordinary setting. Enjoy 360-degree water views from a single deck: sunsets over Edgartown Harbor and sunrises toward Nantucket Sound.

Located just three miles from the Chappaquiddick Ferry, the property sits at the end of a 1,750-foot private peninsula beach, offering true privacy. Guests are encouraged to enjoy beach fires and s’mores, or the Concierge can arrange a traditional New England lobster bake buried on your private beach.

Swimming, Sailing & Water Sports

Cape Poge Bay offers calm, protected waters—noticeably warmer than the Atlantic and free from riptides, making it ideal for children and relaxed swimming. Activities include kayaking, canoeing, paddleboarding, SOL Sunfish sailing, 420 sailboats (for qualified sailors). Bring your own kite and enjoy world-class kiteboarding. Cape Poge Bay previously hosted the International Kiteboarding Championships.

Swim out to the floating Swim Platform, complete with umbrella and chase lounge, to enjoy cocktails. The platform also serves as a deep-water dock with approximately 10 feet of depth.

Fishing & Live-Off-the-Land Experiences

Walk to the legendary “Gut,” designated “Albacore Alley” by Saltwater Fly Fishing magazine. In season, harvest your own quahogs and bay scallops, or paddle with children to Dykes Bridge to collect fresh mussels—an authentic Vineyard tradition.

Classic New England Comforts + Modern Amenities

The Outermost House blends timeless New England character with thoughtful modern upgrades, including Starlink high-speed internet, a professional gym, oversized basement with indoor ping-pong, a Steinway wall piano for sing-alongs, horseshoes, tetherball, limited bicycles and baby carriage.

A whole-house Reverse Osmosis water system installed in 2025 enhances the original water supply. Guests who enjoy slightly saltwater outdoor showers can still be accommodated. In the unlikely event of a temporary interruption, potable under-the-sink RO drinking water and bottled water will be provided.

Concierge services available and recommended such as advanced grocery shopping. Yoga and tennis instruction can be scheduled

Explore Chappaquiddick in our Jeep Wrangler convertible!

The owner's Jeep Wrangler convertible is available for use (for a nominal charge) with a Wasque Beach sticker, ideal for exploring Chappaquiddick’s Atlantic Ocean beaches and surf fishing.

The complex is accessed via a dirt-and-sand road: 4x4 vehicles are recommended for guests unfamiliar with beach driving.

A Vineyard Insider Secret: Easy Edgartown Access

Parking in Edgartown at dinner time is notoriously difficult. Complementary passenger ferry tickets are provided, which include free parking on the Chappaquiddick side. Note: The Chappy Ferry typically closes at midnight.

Simply park your car, walk onto the ferry, and in 5 minutes arrive in Edgartown with no waiting and no lines.

Starlink Internet is available