
House vacation 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.

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 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.

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.

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.

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.

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.
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

Cape Cod multi-structure family compound with Pool

Beautiful home! Clubhouse pool, tennis, basketball
Weekly house rentals

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

Beautiful Edgartown / Katama House

Edgartown Cottage, on bus route, walk to town!

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

Ocean View Cape Cod Beach Cottage
Private house rentals

The Boat House

*NEW! Water Views | Falmouth Heights Beach

New Pristine Luxury Home on Martha's Vineyard

Beautiful lakefront vacation property in Mashpee

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

Fun, Authentic, Waterfront Cottage/air conditioned

Lake Shore Cottage - Waterfront with Beach Access

Edgartown Cottage By The Pond
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Salem Vacation rentals
- York County Vacation rentals
- Bar Harbor Vacation rentals
- 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
- Pinehills Golf Club
- Popponesset Peninsula
- Cape Cod Canal
- The Breakers
- Second Beach
- Coast Guard Beach
- Inkwell Beach
- Cape Cod Inflatable Park
- Easton's Beach





