
House holiday rentals in Chappaquiddick
Find and book unique houses on Airbnb
Top-rated house rentals in Chappaquiddick
Guests agree: These houses are highly rated for location, cleanliness and more.

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.

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach
Welcome to Arrowsmith Cottage! If you are considering bringing your small dog, please first contact me (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as dogs require homeowner's written approval and guest’s agreement to the pet fee and homeowners’ pet rules. We cannot allow cats, birds, or any animals other than one pre-approved dog. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

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.

impeccable cottage STEPS to downtown OB & beach!
Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Vineyard Social-Spacious 5BR Home in Oak Bluffs
Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fantastic outdoor spaces, including a large front Farmers Porch and an oversized Patio with a gas grill. Enjoy all the desired amenities, including an outdoor shower, an open kitchen layout, and a 75" Smart TV. Both walkable and bikeable to Oak Bluffs Center and Harbor you can easily explore the town's lively shops, restaurants, and local attractions.

Private Pond-side Cape Cod Home
Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Lambert's Cove Oceanview Beach Pass Trails nearby
Traditional salt box home set in the forested hills above Lambert's Cove. Short walk / drive to town beach. Perfect for family gatherings, home has 3 bedrooms , a loft for virtual work space or reading room, 1.5 baths plus the fully enclosed outdoor shower, fully stocked kitchen, a deck that has seating for relaxing and also an octagonal picnic table, as well as lots of yard space for children or pups to play. Beach towels along with4 beach chairs provided.

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!

Martha's Vineyard Vacation Home
My place is close to the Bike Path, Edgartown, South Beach, Katama General Store, Katama Farm, Edgartown Lighthouse, great views. Take the bike path either direction for all of the island's attractions. You’ll love my place because of the Renovated Kitchen, Renovated Bathrooms, Comfortable Furniture, Convenience to Everything, Outdoor Shower, Deck. My place is good for couples, solo adventurers, and families (with kids).

Close to Edgartown Village Center!
This 1800 square foot Ranch-style Condo with loft was built in 2018 and is set on a large nicely landscaped lot with plenty of room inside and out. It has 3 bedrooms and a loft and sleeps 9. It’s a 20-minute walk to the Edgartown village center, a 10-minute walk to Morning Glory Farm, and just a 10-minute drive to South Beach! All updated furnishings, beds, linens, appliances. Read our reviews! Immaculate!

Walk To Town - Beautiful Edgartown Cottage
Walk to downtown Edgartown in minutes from this newly renovated 3BR/2BA home just off Upper Main St. Enjoy new bathrooms, a modern kitchen, and bright, stylish living spaces. Just a 10-min stroll to top restaurants, shops, and the harbor. Bike to South Beach or State Beach via scenic paths just moments from our home. The perfect blend of location, comfort, and summer living on Martha’s Vineyard.

Katama Barn
Selected dog friendly, Immaculate beach house this is the perfect property to bike to the beach and then to dinner in Edgartown. 1.2 miles from beach South Beach, and 1 mile from Edgartown's Main Street. Outdoor shower, large private yard.heated bathroom floors, a/c, heat, modern kitchen, brand new appliances/washer dryer, sleeping loft, and separate storage loft. Location, location, location.
Popular amenities for Chappaquiddick house rentals
House rentals with a pool

Private Pool, near beaches, 3 BR/3 BA, Central Air

Modern & Spacious Edgartown Home with Pool

Beautiful Edgartown 3500 sq ft home, heated pool

Coastal Charm New Seabury: 5BRs with Private Pool

Chic Oak Bluffs Home with Hot Tub, Walk to Town

Renovated ranch with pool access

Summer Serenity on Cape Cod (heated pool)

Waterfront Home w/Dock, Deck, Central A/C & Kayaks
Weekly house rentals

Chappaquidick contemporary cottage with sauna

Chappaquiddick Island - Whispering Pines

Martha's Vineyard Cottage: Walk to Town and Beach

Edgartown Village/ Sun-filled Home/walk to town

The Blue Lagoon, Oak Bluffs

Lovely Farm View on Llewellyn

On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach

Beautiful Edgartown / Katama House
Private house rentals

The Boat House

The Kennedy Guesthouse

South Beach | Katama | Outdoor Shower

Vineyard Meadow Writer's Cottage with Hot Tub

Cottage + Guest House | Beach 100 Yards | Sleeps 8

Lake Shore Cottage - Waterfront with Beach Access

Pinkletink Plantation

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
Destinations to explore
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- Bonnet Shores Beach
- East Sandwich Beach
- Duxbury Beach
- Easton Beach
- Saquish Beach
- Sandy Neck Beach
- Nauset Beach
- New Silver Beach
- Skaket Beach
- Falmouth Heights Beach
- Popponesset Peninsula
- Cape Cod Canal
- Pinehills Golf Club
- The Breakers
- Inkwell Beach
- Second Beach
- Coast Guard Beach
- Cape Cod Inflatable Park
- Easton's Beach





