
House vacation rentals in Chappaquiddick
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Top-rated house rentals in Chappaquiddick
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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

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.

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.

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

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.

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.

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).
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

ShoestringBayHouse, waterfront & pool in Cotuit

Coastal Charm New Seabury: 5BRs with Private Pool

Cape Cod multi-structure family compound with Pool

Chic Oak Bluffs Home with Hot Tub, Walk to Town

Renovated ranch with pool access
Weekly house rentals

The Blue Lagoon, Oak Bluffs

Beautiful Edgartown / Katama House

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

Valentine's Retreat Hot Tub Fire Pit Trails Beach

Edgartown Cottage, on bus route, walk to town!

The Kennedy Guesthouse

Newer construction Edgartown with AC, new furn.

Oak Bluffs 4BR • 5 Min Drive to Downtown
Private house rentals

Custom crafted Makonikey home

Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ

Beautiful lakefront vacation property in Mashpee

Edgartown Cottage By The Pond

Lake Shore Cottage - Waterfront with Beach Access

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

Charming 3-Bedrm w/Loft.New Construct! Walk 2 town

The Boat House
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