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Chappaquiddick Island Vacation Rentals

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    Check prices for these dates, December 13 – 14, 2026

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    Our top choices for Chappaquiddick Island vacation rentals

    1. The Club at New Seabury

    A golf course with a clubhouse, a lake, and surrounding trees.

    2. InnSeason Resorts Captain's Quarters

    A hotel room with a large bed, two bedside lamps, a wooden nightstand, and a view of a balcony with outdoor furniture.

    3. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

    Room

    4. Walk to Beach & Lighthouse: Oak Bluffs Studio!

    An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

    5. Charming studio in tranquil Falmouth with AC

    A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

    6. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

    A boat docked at a concrete pier with a sandy shore in the background.

    7. Charming Guesthouse | Walk to Beach | Downtown

    Exterior

    8. Oak Bluffs 4BR • 5 Min Drive to Downtown

    A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

    9. Vineyard Luxury "Yurt"

    A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

    10. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

    A circular stone patio with Adirondack chairs and a small table in a forested area.

    11. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

    A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

    12. LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

    A wooden staircase leading to a beach area with a small building and a view of the ocean.

    13. Love Sand, Madaket on the Beach, Lovely Seaside Home

    A two-story house with a balcony, a front porch with columns, and a sign that reads 'LIVE SWIM'.

    14. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

    A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

    15. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

    A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

    16. Nantucket - on the outskirts of the city

    A single-story house with a brick chimney, white trim, and a small porch.

    17. Coastal chic meets French Provençal in this newly renovated oceanfront home.

    A covered outdoor seating area with a view of the ocean, a ceiling fan, and a flat-screen TV on the wall.

    18. Spacious 5BR Falmouth Family Retreat with Deck, Ping Pong Table & Central A/C

    A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

    19. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

    A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

    20. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

    A kitchen with a dining area, a ceiling fan, and a view to an outdoor patio.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Top Chappaquiddick Island Hotel Reviews

    Vineyard Square Hotel & Suites

    A multi-story hotel with a grand entrance, a flagpole, and a well-lit facade.

    Harbor View Hotel

    A spacious living area with a dining table, sofas, and a view of the sea.

    Faraway Martha's Vineyard

    A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

    Inn on the Sound

    A cozy room with wicker furniture, a stone fireplace, and a view of the ocean.

    InnSeason Resorts Captain's Quarters

    A hotel room with a large bed, two bedside lamps, a wooden nightstand, and a view of a balcony with outdoor furniture.

    Shore Haven Inn

    A large, multi-story house with a covered porch and a well-maintained lawn.

    The Palmer House Inn

    An outdoor patio with a fire table, seating, and a table set for a meal.

    Inn on the Square

    A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.

    Vineyard Harbor Motel - Private Beach

    A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.

    Madison Inn

    A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

    The Franklin Hotel Martha's Vineyard

    A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

    Admiralty Inn & Suites - a Red Collection Hotel

    A modern hotel room with a large bed, a separate bathroom with a bathtub, and a blue rug.

    Red Horse Inn

    Exterior

    Hyannis Travel Inn

    A man sitting at a table with a laptop, overlooking a pool area with chairs and tables.

    Frederick William House

    A two-story house with a stone facade, a balcony, and a well-maintained garden.

    The Coonamessett

    A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

    Iris Hotel Cape Cod

    A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.

    Find out more about Chappaquiddick Island

    Everything you need to know about Chappaquiddick Island vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaquiddick Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaquiddick Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Chappaquiddick Island vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Chappaquiddick Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chappaquiddick Island in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Chappaquiddick Island rentals

    At Expedia, we put the best Chappaquiddick Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Chappaquiddick Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaquiddick Island vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaquiddick Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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