Holiday rentals in Chappaquiddick

Chappy cottage close to ferry & walk to beach

Booking for '26 Season. Charming cottage is a 5-minute bike ride to the Chappy ferry & beach and a 10-15 minute walk to the 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.

Private Garden Oasis -Outdoor Shower- Walk to town

* Private garden patio: string lights create chill evenings around the propane fire pit. Table & chairs, propane grill, & 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

Sunset on Shore - Lewis Bay Waterfront

NEW LISTING! Built in the 1930s, this is the kind of beach house that invites you to unplug (don’t worry-there’s WiFi). With views of Lewis Bay from every room, private stairs to the water, a big deck, lawn, and outdoor shower, it’s all about the location and the view. Inside, it’s Olde Cape Cod-window A/C, a butter-yellow kitchen, and the kind of charm that takes you back-nostalgic in all the right ways and the best seat for every sunset. Bring your boat-a ramp is located at Englewood Beach.

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

The Big Chill is close to the buses, grocery stores, fish markets, Morning Glory Farm, the beautiful beaches and the center of Edgartown. You’ll love it.. its cozy, has A/C, you'll love the high ceilings on the second floor and the location! The BIG CHILL has a full bath indoors and a fully enclosed outdoor shower steps from the door. Great for couples, solo adventurers, and business travelers….a bike ride to town. If you need a bigger house, check out Sandy Feet Retreat for 5-10 guests.

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

Martha's Vineyard Cottage: Walk to Town and Beach

Updated 1920s Cottage in Edgartown Village – Walk to Beach, Harbor and Main Street Step into classic Vineyard charm at this fully updated 4-bed, 3-bath craftsman cottage in the heart of Edgartown. Two blocks from Main Street’s restaurants, galleries, and harbor and a quick walk to Fuller St Beach & Lighthouse Beach. Fully winterized + AC, high-speed Wi-Fi, three workstations. Ideal for families, bachelorette parties or anyone craving a New England coastal escape.

111I Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

New Woodland Escape, Walk To Beach and Bike Path,

Escape to a newly renovated woodland retreat just 0.8 miles from Chapoquoit Beach. This spacious three-story home offers four bedrooms, four bathrooms, multiple bonus sleeping spaces, a two-car garage, and a beautiful kitchen with bar seating and a wine fridge. Watch birds from the open-air tower, spot wildlife from the glass-front patio, grill beneath the trees, or bike the nearby Falmouth path to Woods Hole. Family-friendly essentials are included.

Stroll to Edgartown, AC, NEW Remodel, NEW Listing!

Sneak in through the back door of this light filled cottage. Soup to nuts, almost everything is new! Including, Bosch appliances, wifi, tv, AC, furniture, BBQ, new deck with dining and lounging area, fire pit and outdoor shower. Walk to historical Edgartown village. Under a mile to Fuller Street Beach. Bike to Morning Glory farms! Kids will love the nearby library and playground. Walk to the grocery store, Dairy Queen and so much more!

Katama Loft

Very cute clean apt with private outdoor space. 1.5 miles to either downtown or beach. 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. Thoughtful touches throughout and your comfort always in mind

The Blue Lagoon, Oak Bluffs

Come enjoy this beautifully designed, brand new home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An outdoor patio with gas grill is the perfect spot to relax after a day at the beach. Just a few steps away is the lagoon where you can paddle board, kayak, dig clams, or just take in the amazing sunsets! Summer rentals are Saturday to Saturday. Please send a message if you have any questions.