Holiday rentals in Chappaquiddick

Walk to downtown Edgartown in a quiet neighborhood

This house is on a peaceful side street just a 15-min walk to Edgartown Village. It has 3 bedrooms, 1 bath, a well-equipped kitchen, a porch, and a grill for summer cooking! This space is a second-floor unit; the first floor is occupied by the owner. Both units are completely separate with private entrances and no shared spaces. Close to multiple popular beaches, the town library and playground, and just around the corner from the island's largest grocery store make this a great home base!

Ferry Tickets Available - Cozy Coastal Hideaway

✔Beach! ✔Downtown! ✔Restaurants/Bars! ✔Bike Path! Summer Ferry Tickets are available Sun to Sun. Island Grove is the place to be, tennis and in proximity to the Island-favorite Morning Glory Farm and the bike path to Edgartown Village, and South Beach. Our home features three bedrooms (king, queen, two twins), deck w/awning, A/C, and an easy bike ride to town or beach. Quiet, relaxing and close to the best of Edgartown and the Vineyard. We provide bed linens and bath towels (many don't).

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

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

Chappy Beach House

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.

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

Vineyard Meadow Writer's Cottage with Hot Tub

This lovely retreat is just steps from miles of trails. Walk to the beach or meander through woods of Long Point Wildlife Refuge, experiencing the serenity of this untouched corner of Martha's Vineyard. After a day of enjoying the outdoors, come home to the light and airy writer's retreat. The HOT TUB IS OPEN! It also has an outdoor shower and a wonderful kitchen. This is the perfect location for a get-away with family and friends or for a creative retreat with your fellow artists.

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!

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

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.

El Refugio - cottage house

Welcome to El Refugio (the refuge), a brand-new carriage house on Wing Pond with direct canoe access. Nestled along the Shining Sea Bike Path, enjoy biking to two nearby beaches and exploring beautiful walking trails. This peaceful retreat, with owners in the neighboring house, is perfect for short or long stays, offering modern amenities and special long-term off-season discounts. Surrounded by lush greenery, El Refugio is your perfect escape to nature and tranquility.