Chappaquiddick Island vacation rentals

Spacious, Old Vineyard charm with Private Beach

This is a classic, rare vintage Vineyard property: a beautifully simple, comfortable, and charming family house located directly on its own private beach on Katama Bay. Peaceful and secluded, yet a short walk or bike ride to the popular, public surf beach, and 3 miles from bustling, historic Edgartown. The house is both intimate and expansive: equally perfect for small families or larger groups, for quiet retreats or festive reunions. Spacious and soulful indoors and out. A magical refuge. .

Step Away; A Martha's Vineyard Retreat

Studio apartment addition attached to our family home. Our home is located three miles to downtown Edgartown with bus service & bike path close by. Private entrance, mini fridge, coffee press & accessories, private bath with shower, washer/dryer, bed in a loft area (ladder access only) with queen size sofa bed available below for additional sleeping. This is our family home with two baby boys. We try our best to keep quiet, but it is important to note their presence; rental has a sound machine.

Chappy cottage close to ferry & walk to beach

Charming and renovated cottage is a 5-minute bike ride to the Chappy ferry point & beach and a 10-15 minute walk to the Mary Frances Preserve beach. Located in a quiet wooded setting, the property offers new furniture and beds; renovated kitchen with dishwasher and microwave; new bath w/ shower/tub; washer/dryer; hardwood; screen porch; deck & outdoor shower. Cable, wifi (200 megs), AC, ceiling fan, grill, deck furniture, beach chairs & umbrella. The rental season runs mid May through late Oct.

Katama Loft

Newly remolded apt 2 miles to either downtown or beach with bike path across the street! Restaurants and general store within a half mile. One bedroom ,living room area, kitchen with stove, microwave, and convection oven and cookware. Grill, outdoor dining, smart tv, wifi, beach gear, laundry, and more! Bikes and kayaks available on request. Apartment is just newly renovated August 2022 (was rented year round for past 7 years). Thoughtful touches throughout and your comfort always in mind.

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

Sweet Triangle loft, close to beach, free parking

Great for couples or families with young kids (not ideal for 4 adults), centrally located. Enjoy the Vineyard with a car (free parking) or without, from here. * On the bike path * 1 mile from State Beach * 1 mile from Main Street, Edgartown & Chappy ferry * Close to trail walking paths * walking distance to restaurants * walking distance to groceries * On VTA bus line ( easy access to all towns/ferries) We send guide book with recs on food, activities, etc upon booking

Chappy Whispering Pines

Peace and quiet, and access to fabulous East Beach, Mytoy, Wasque and the many wonderful walking trails of Chappaquiddick, this lovely home among "whispering Pines" will be your warm welcoming retreat after a day at the beach, exploring Chappy by bike or fishing to your hearts delight. We provide a comfy, well furnished and beautifully decorated home outfitted with all cotton bedding, linens and fresh pillows, and lovely quilts, wool and cotton rugs, and so much more.

Stylish retreat | walk to town | fire pit

* Private garden patio: table & chairs, propane grill, propane fire pit & enclosed outdoor shower * 10 min walk to Edgartown's dining & boutiques * Cable TV, Streaming services, Sonos * High-speed WiFi, comfortable workspace in the bedroom * USB charging ports in the BR & LR * Small but mighty fully stocked kitchen for home-cooked meals * Organic, local bath products * Board games & a small library * HW floors, SS Bosch appliances, DW, W/D, HVAC