
House vacation rentals in Chappaquiddick
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Top-rated house rentals in Chappaquiddick
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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.
4.92 out of 5 average rating, 106 reviews
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.
5.0 out of 5 average rating, 32 reviews
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
4.92 out of 5 average rating, 212 reviews
**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.
4.96 out of 5 average rating, 135 reviews
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.
5.0 out of 5 average rating, 4 reviews
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.
4.95 out of 5 average rating, 19 reviews
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.
4.93 out of 5 average rating, 113 reviews
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.
5.0 out of 5 average rating, 170 reviews
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!
4.93 out of 5 average rating, 322 reviews
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).
4.87 out of 5 average rating, 180 reviews
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!
4.98 out of 5 average rating, 193 reviews
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.
4.95 out of 5 average rating, 142 reviewsPopular amenities for Chappaquiddick house rentals
House rentals with a pool

Private Pool, near beaches, 3 BR/3 BA, Central Air
4.96 out of 5 average rating, 143 reviews
Modern & Spacious Edgartown Home with Pool
5.0 out of 5 average rating, 23 reviews
Beautiful Edgartown 3500 sq ft home, heated pool
4.93 out of 5 average rating, 57 reviews
Coastal Charm New Seabury: 5BRs with Private Pool
4.94 out of 5 average rating, 51 reviews
Chic Oak Bluffs Home with Hot Tub, Walk to Town
5.0 out of 5 average rating, 20 reviews
Renovated ranch with pool access
4.98 out of 5 average rating, 40 reviews
Cape Cod multi-structure family compound with Pool
5.0 out of 5 average rating, 25 reviews
Beautiful home! Clubhouse pool, tennis, basketball
5.0 out of 5 average rating, 30 reviewsWeekly house rentals

Martha's Vineyard Cottage: Walk to Town and Beach
5.0 out of 5 average rating, 28 reviews
Edgartown Village/ Sun-filled Home/walk to town
4.85 out of 5 average rating, 61 reviews
The Blue Lagoon, Oak Bluffs
4.98 out of 5 average rating, 55 reviews
Lovely Farm View on Llewellyn
4.94 out of 5 average rating, 16 reviews
Beautiful Edgartown / Katama House
4.98 out of 5 average rating, 47 reviews
Edgartown Cottage, on bus route, walk to town!
4.86 out of 5 average rating, 80 reviews
On HGTV! Gorgeous, AC, Hot Tub, WALK Town & Beach
4.99 out of 5 average rating, 78 reviews
Ocean View Cape Cod Beach Cottage
5.0 out of 5 average rating, 44 reviewsPrivate house rentals

The Boat House
4.86 out of 5 average rating, 37 reviews
*NEW! Water Views | Falmouth Heights Beach
5.0 out of 5 average rating, 8 reviews
New Pristine Luxury Home on Martha's Vineyard
4.98 out of 5 average rating, 91 reviews
Beautiful lakefront vacation property in Mashpee
4.96 out of 5 average rating, 94 reviews
Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course
4.96 out of 5 average rating, 45 reviews
Fun, Authentic, Waterfront Cottage/air conditioned
4.98 out of 5 average rating, 50 reviews
Lake Shore Cottage - Waterfront with Beach Access
5.0 out of 5 average rating, 34 reviews
Edgartown Cottage By The Pond
4.9 out of 5 average rating, 62 reviewsDestinations to explore
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