Vacation rentals in Chappaquiddick

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Top-rated vacation rentals in Chappaquiddick

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A charming two-story cottage features a shingled exterior with yellow trim. A white picket fence encloses the front yard, which is landscaped with greenery. Windows allow natural light to illuminate the interior. Clear blue skies and fluffy clouds provide a serene backdrop.

Cottage in Oak Bluffs

5 out of 5 average rating, 8 reviews

The Island Collection MV: Sandy Shores

Your vacation stay will be unforgettable in this charming cottage. Being on vacation in Martha's Vineyard in the heart of downtown Oak Bluffs has its privileges! You are close to shopping, nightlife, and restaurants and lots of fun! Located 100 ft from the beach, this lovely furnished cottage has 2 full bedrooms, 2 full private bathrooms, and 1 powder room. There is one parking space available, and the patio has a gas grill for outdoor dining. Tenant brings own linens/sheets/towels/beach towels.

Top guest favorite

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

Apartment in Oak Bluffs

4.92 out of 5 average rating, 109 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Guest favorite

The serene water reflects the soft colors of a sunset, with hints of pink and orange blending into the sky. Lush greenery surrounds the calm water, creating a tranquil atmosphere. Gentle ripples are visible on the surface, enhancing the peaceful setting.

Home in Barnstable

4.86 out of 5 average rating, 148 reviews

Cottage with private beach in Hyannis Port

Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Guest favorite

Home in Mashpee

4.94 out of 5 average rating, 110 reviews

Newly Renovated! Seconds to sand, fire pit, A/C

Recently Renovated! This Cape Cod Cottage is completely refreshed top to bottom. Less than 60 seconds to the sand. Cape cod vacations do not get any better than this! Located on idyllic Monomoscoy Island known for its gorgeous wildlife and stunning waterways, our home is the perfect choice to rent on Cape Cod. We are less than 10 Mins to Mashpee Commons and famous Mashpee Town Beach, Less than 5 mins to New Seabury and the Popponesset Inn, and only 15 mins to downtown Falmouth. Linens included!

Superhost

Home in Falmouth

4.86 out of 5 average rating, 35 reviews

Cape Vacation in style! Close to Main St & Beaches

We affectionately call this house 'The Local,' as it sits in the heart of beautiful Falmouth, within short walking distance to the quaint Main St. shops, delectable restaurants, fish markets, entertainment like bowling and axe-throwing (!), and is a short drive to Woods Hole and many of the Cape's most breathtaking beaches along the coast. Great summer or off-season destination, the house is complete with high-end finishes and furnishings to make your vacation especially comfortable. Enjoy!

Superhost

Condo in Yarmouth

4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 19-26. Sleeps 8

This unit is on second level. It is a beautifully renovated two-bedroom/two and a half -bathroom unit, sleeps eight. Available July 19-July 26, 2025. NO ELEVATOR to 2nd floor. Master king-size bedroom en-suite; second ensuite bedroom has two full-size beds; there is a sleeper sofa in living room, hallway half bath. All rooms have sliders to beautiful river view and TVs. Full-size fridge in unit. Indoor pool/hot tub. Access fully equipped kitchen, washer/dryer, exercise room, indoorpool.

Guest favorite

The kitchen features a spacious granite countertop with seating at three bar stools. Large windows and overhead lighting enhance the bright and airy atmosphere. Appliances including a stove and refrigerator are integrated into the cabinetry, providing a modern look in the renovated space.

Apartment in Oak Bluffs

4.95 out of 5 average rating, 168 reviews

Beautiful private apartment walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

Guest favorite

Home in Mashpee

4.93 out of 5 average rating, 44 reviews

Tranquil Cape getaway#2 with AC Kid & Pet friendly

Welcome to this peaceful Cape retreat! With its charming Cape style home and serene surroundings, this two-level residence offers a perfect getaway for relaxation and quality time with loved ones. Property Features: Four Cozy Bedrooms Outdoor Deck and Grill Complete Fenced-In Yard Swing Set Whether you're looking to relax indoors, enjoy outdoor activities, or spend quality time with family and friends, this idyllic haven offers all the necessary amenities for a memorable vacation.

Top guest favorite

A circular arrangement of chairs in various colors surrounds a small stone fire pit. The scene overlooks a serene pond, framed by lush trees and bathed in warm sunlight. Subtle outdoor lighting is positioned along the perimeter.

Cottage in Barnstable

4.99 out of 5 average rating, 142 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Superhost

Home in Edgartown

4.91 out of 5 average rating, 54 reviews

Updated Beautiful Cottage in Edgartown AC

A true island charmer. Light, airy and central-air-conditioned home offers all the comforts of modern living centrally located in Edgartown. Recently completed extensive upgrades completed enhance all of the space, including a new kitchen, both bathrooms, basement, and more. A spacious outdoor furnished deck with enclosed outdoor shower and an expansive grassy lawn make for a great space to relax. Great location makes Island travel a breeze.

Superhost

A wooden gazebo is nestled among lush greenery, featuring an intricate design and a shingled roof. A well-maintained stone pathway, lined with soft lighting, leads through the vibrant grass and towards a backdrop of surrounding trees and a deck area.

Home in Falmouth

4.9 out of 5 average rating, 48 reviews

Cape Cod's Best Winter Getaway / Hidden Gem

Nestled amidst snow-draped trees, a winter getaway house stands like a hidden gem in a sea of white. Its charming open concept and stone hearth exude a warmth that beckons, a refuge from the biting chill. Inside, the crackle of a glowing fireplace mingles with the scent of pine and hot cocoa. Here, time slows, and the world melts away, leaving only peace, comfort, and the hush of a winter wonderland.

Top guest favorite

The kitchen features sleek black countertops and white cabinetry, creating a contemporary look. Stainless steel appliances, including a microwave and refrigerator, are present. A window above the sink allows natural light to illuminate the space, enhancing the overall brightness of the room.

Home in Yarmouth

5 out of 5 average rating, 9 reviews

Cape Escape House

Beautiful freshly renovated house . Your family will be close to everything when you stay at this centrally-located place. Short walk to the beach with playground and access to public boat launch ramp. Walk to restaurants, coffee shop, liquor superstore and local shopping plaza. Located on a quiet street with plenty of parking. Fenced in backyard with patio and grill.