Holiday houses in Chappaquiddick

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

Value · Family · Barbecue

Walk to EDG Wharf - Outdoor Shower, AC, and Grill

Just a short walk to Edgartown's shops & restaurants, this cape style home features open concept living, stainless steel appliances, bamboo floors, oversize 2 car garage, washer/dryer and outdoor shower! The master suite includes a sitting area, walk in closet & attached bath with walk-in shower, soaking tub & double vanity. Additional 3 BRs include queen/twin beds & 2 full baths. Kitchen sliders lead to outdoor brick patio with BBQ and dining area. Outdoors games and four bikes included.

Family · Value · Hospitality

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.

Family · Location · Access

Edgartown Village Classic

Charming 4BR/3BA home in Edgartown’s Historic District. Walk to shops, restaurants, and the harbor. Comfortable and spacious—perfect for families. Features include a well-equipped kitchen, cozy living space, and a private backyard with grill, dining area, and lounge chairs. Enjoy the best of the Vineyard from this ideally located retreat—just minutes from beaches, bike paths, and everything Edgartown has to offer. Pricing based on four person occupancy. Pricing for additional two on request.

Location · Accuracy · Comfort

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.

Family · Location · Bathroom

**Vineyard Vacation Retreat** -3 BR

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

Location · Value · Laundry

The Seashell Cove - Martha's Vineyard

Nestled in the exclusive Katama neighborhood of Edgartown, this sunny Cape retreat is perfect for families or friends. Just two miles from South Beach, it offers cozy interiors, high-speed Wi-Fi, and smart TVs. Outdoors, enjoy a farmer's porch, deck with a direct gas-line grill, and spacious yards. Close to downtown Edgartown, bike paths, and attractions like the Chappaquiddick ferry, this property is ideal for both summer adventures and peaceful off-season stays.

Family · Value · Pets

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.

Location · Family · Hospitality

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!

Family · Value · Beach

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!

Family · Location · Cleanliness

Beautiful Edgartown / Katama House

The house is located a short drive, bike, or walk from Edgartown center, one of the nicest towns on the East Coast. In the property you will find an expansive well stocked kitchen ready for all your culinary needs. 3 beautiful bedrooms that sleep 6 along with the sun room being equipped with a queen sofa bed. The house boasts a large backyard with an outside grill, dining table on the full patio, and many places to relax.

Value · Family · Biking

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.

Family · Location · Barbecue