Holiday houses in Chappaquiddick

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chappaquiddick

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1

Guest favourite

The exterior of a single-story house is depicted, featuring a landscaped yard with lush green grass and vibrant pink flowering bushes. A wooden front step leads to the doorway, framed by large windows that allow natural light into the interior.

Home in Edgartown

4.85 out of 5 average rating, 61 reviews

Edgartown Village/ Sun-filled Home/walk to town

Cozy home 10 minute walk to the fine dining and shopping that Edgartown Village offers. Bike path and bus stop are at the end of the street providing easy access to State (1 mile) and South (2.5 miles) Beaches. Living room has a flat screen TV, seating for all guests. Sunroom with seating and comforting breezes. Sun filled yard offers privacy and deck with sofa set and grill . A separate patio has a fire dining table. Pets are considered (contact owner). Saturday to Saturday rental 6/17 to 9/23

FamilyLocationIndoor spaces

Top Guest favourite

A private garden patio is showcased, featuring a circular table surrounded by four chairs. Plush cushions in vibrant blue patterns adorn the seating. Nearby, two wooden lounge chairs offer additional relaxation options. Lush greenery and flowers provide a natural backdrop, enhancing the outdoor ambiance.

Apartment in Edgartown

5.0 out of 5 average rating, 127 reviews

Couples Getaway Carriage House- Walk to Edgartown

* 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

FamilyValueParking

Top Guest favourite

A charming cottage features a shingle exterior surrounded by lush greenery. Large windows invite natural light, and a welcoming entryway is accentuated by steps leading to the front door. The tranquil wooded setting enhances the peaceful atmosphere of the property.

Cottage in Chappaquiddick

4.98 out of 5 average rating, 83 reviews

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.

FamilyLocationIndoor spaces

Guest favourite

A two-story house is situated among trees with fresh green leaves. A wooden staircase leads to the entrance on the upper level, while a gravel driveway provides access to the home. The exterior features dark wood siding complemented by teal trim.

Home in Chappaquiddick

5.0 out of 5 average rating, 32 reviews

Chappy Beach House *DERBY DATES!*

Welcome to this charming 4-bedroom retreat tucked just off Chappaquiddick’s only paved road. Perfectly situated minutes from the Chappy Ferry, downtown Edgartown, and some of the island’s most pristine, uncrowded beaches. Features include AC, high-speed WiFi, a washer/dryer, and a gas grill for laid-back summer dinners. Whether you’re a longtime Vineyard lover or discovering Chappy for the first time, this home offers the ideal base to experience the island’s quiet beauty and classic charm.

FamilyLocationAccuracy

Top Guest favourite

A bright living area features a comfortable seating arrangement with soft, neutral-toned couches. Natural light fills the space through multiple windows, and a rustic wooden coffee table enhances the cozy feel. A small dining area is visible in the background.

Guesthouse in Edgartown

5.0 out of 5 average rating, 26 reviews

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.

LocationFamilyOutdoor spaces

Superhost

A custom-built home is depicted with a charming shingle exterior and a symmetrical roof. The front porch is flanked by well-maintained landscaping, including flower beds. Several windows allow natural light to illuminate the inviting entryway, creating an accessible and welcoming façade.

Home in Edgartown

4.94 out of 5 average rating, 16 reviews

Lovely Farm View on Llewellyn

Custom built home with beautiful backyard views of Morning Glory Farm’s produce fields. The home features 4 bedrooms including 3 king beds, 1 queen bed, and a twin trundle bed and an additional pull-out couch in a common area. The kitchen is fully equipped with all essentials and perfect for preparing a meal for a large group. Located 1.5 miles from downtown Edgartown and a 10 minute drive to nearby beaches. Other towns such as Oak Bluffs or Vineyard Haven are a short 12 minute drive away.

LocationFamilyQuiet

Superhost

A contemporary home with a light-colored wooden exterior, framed by a manicured lawn and trees. The welcoming front porch features stairs leading to double doors, while a deck adorned with wooden railings invites relaxation amidst a lush natural setting.

Home in Chappaquiddick

5.0 out of 5 average rating, 4 reviews

Chappaquidick contemporary cottage with sauna

This unique place has a style all its own. Contemporary 3 bedroom 2 bathroom home in heart of chappaquidick island . Off the main road close to Mytoi garden , waque and dike bridge. Bike to the beach . And best of it all is the Outdoor shower . Just ferry ride To Edgartown to enjoy morning stroll or have dinner. Equipped with echelon cycling bike sauna and ping pong table. Enjoy bbq on deck .washing machine and dryer available for use All bed have linen and quilt blankets.

LocationQuietComfort

Guest favourite

A cozy living area is highlighted by a plush blue sofa and a wooden coffee table. A flat-screen television is placed on a white console. Natural light filters in through two skylights, and sliding glass doors lead to an outdoor space featuring a pool.

Home in Chappaquiddick

4.95 out of 5 average rating, 19 reviews

Chappaquiddick Island - 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.

FamilyLocationCleanliness

Top Guest favourite

A charming two-story cottage features a shingled exterior with a pitched roof. The inviting front porch is supported by wooden pillars and surrounded by lush greenery. A white picket fence encloses the well-kept lawn, creating a warm curbside appeal.

Home in Edgartown

5.0 out of 5 average rating, 28 reviews

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.

ValueLocationWalkability

Top Guest favourite

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

4.93 out of 5 average rating, 321 reviews

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!

LocationFamilyNearby

Guest favourite

A bright living space features white walls and a wooden ceiling with ample natural light. A round coffee table is centered in the room, surrounded by a sofa and wicker chairs. A side table holds a lamp, and a colorful artwork is displayed on the wall, with ocean views visible through windows.

Cottage in Chappaquiddick

5.0 out of 5 average rating, 16 reviews

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a 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!

FamilyLocationGetting around

Guest favourite

A charming guest house is surrounded by thriving greenery and well-maintained grass. A stone pathway leads to the entrance, with large windows on the front exposing a glimpse of the interior. Mature trees provide natural shade and enhance the serene atmosphere of the property.

Cottage in Edgartown

5.0 out of 5 average rating, 8 reviews

Charming Katama Couples Cottage

Located in a prime Katama location, this one-bedroom, one-bathroom guest house is the perfect hotel alternative. It features a full kitchen, dining area, living room, and full bathroom on the first floor. The second floor offers a cozy bedroom with a large closet. Ideal for a couple looking to enjoy Martha’s Vineyard. There is a private outdoor shower. Please note: the main house on the property is occupied by the owners.

FamilyLocationAccuracy