Beachfront vacation rentals in Dukes County

4.94 out of 5 average rating, 63 reviews

The exterior of the house is surrounded by lush greenery, featuring a spacious yard with a picnic table and a stone wall. A guest cottage is visible, alongside a deck with outdoor seating and an umbrella. Tall trees provide shade on a sunny day.

Home in Oak Bluffs

First-class 4+ BR Lagoon Pond Camp

Ultimate getaway house!!! Situated on Lagoon Pond in Oak Bluffs. Sleeps 10 people plus 2 in the optional guest cottage. The house is proximate to OB center - convenient for walking and bike riding. Beach access! The house boasts an outdoor pizza oven, outdoor nooks (hammocks!), and a spacious yard. There are amenities galore including, but not limited to: an outdoor shower, grill, board games, wifi, cable & roku, towels, linens, etc. 1 week min stay, with Sunday turnovers in July & August!

Top guest favorite

A serene view of the ocean is framed by white wooden architecture. The calm water reflects a clear blue sky, while a sandy beach lies in the foreground, accompanied by a stone jetty. Benches are positioned along the walkway, inviting relaxation.

Condo in Oak Bluffs

5 out of 5 average rating, 28 reviews

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

Enjoy one of the most desirable locations on the Vineyard!! Enjoy AMAZING sunrises & gorgeous ocean views from this lovingly kept, super clean condo. Literally across the street from town beach, adjacent to Waban Park, a few blocks to Ocean Park, Flying Horses, Steamship Authority & downtown Circuit Avenue (restaurants, shops)! Bring a car (one unreserved parking spot) or walk over from the boat. Bike delivery & storage available. We hope to see you this summer in this fantastic summer condo!

The cottage exterior is framed by lush greenery and stone landscaping, featuring a welcoming porch with rocking chairs. Colorful flower pots and pumpkins are placed around, while a serene view of the water is visible in the background.

Cottage in Oak Bluffs

5 out of 5 average rating, 3 reviews

The WestLake

This unique 3-level Vineyard style cottage perched on a 25' bluff offers you a panoramic view of the Lagoon's shimmering waters, and private beach access to the Nantucket Sound. From across the bay, you can see and faintly hear the Vineyard Haven Ferry departing. Simply follow the wooded path leading to over 110 feet of your own sandy beach with clean, calm waters which allows for safe kayaking and canoeing yet has the perfect breezes for windsurfing and sailing from your own mooring.

Top guest favorite

A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.

Cottage in Edgartown

5 out of 5 average rating, 21 reviews

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

The exterior of a classic Cape home is showcased, featuring shingle siding and white trim. A welcoming entrance is highlighted by a red door and a white porch. Lush greenery surrounds the house, with a pink chair positioned on the porch.

4.95 out of 5 average rating, 19 reviews

Woods Hole with views of Great Harbor.

Stunning water views in both directions. A large private backyard, Plenty of spaces to gather or have some solitude. A short walk away from Stony Beach, Woods Hole village with its various delicious restaurants, and the Martha's Vineyard Ferry. Parking in the driveway can accommodate two cars. Pets are allowed upon approval with a $50 fee. *Please see my personal reviews for previous reviews of the property. *WE ARE BOOKED ⬇️ JULY 1 - OCTOBER 1 2026

New place to stay

Mill Pond Family Retreat

🌊 Welcome to Your Cape Escape — Sleeps 7 | Falmouth, MA Your Cape escape begins here! Located in Falmouth and only a quick stroll or ride to the beach, this cozy and spacious home features a lovely view of Mill Pond. With downtown Falmouth and Woods Hole both close by, you’ll be right in the middle of classic Cape Cod beaches, dining, shops, and coastal adventures.

4.89 out of 5 average rating, 61 reviews

A charming waterfront cottage is depicted, featuring a light gray shingle exterior and a welcoming entryway with wooden steps. The expansive ocean view is visible in the background, enhancing the serene landscape, with clear skies and greenery surrounding the property.

Home in Chilmark

Cozy Waterfront Cottage, Newly Remodeled!

Beautifully upgraded WATERFRONT cottage in Menemsha with (essentially a) PRIVATE BEACH! Direct access to Vineyard Sound from your own staircase leading down to the water’s edge. Enjoy stunning sunsets and breathtaking views from every room. Private and peaceful but conveniently located just a short drive or bike ride to Menemsha or the Chilmark village center.

An aerial view showcases the property nestled along Edgartown Harbor, surrounded by lush greenery. Boats are docked along the marina, with well-maintained gardens visible near the buildings. The architecture reflects the local charm, complementing the serene waterfront setting.

Apartment in Edgartown

Edgartown Harbor King Suite

Martha’s Vineyard has plenty of family-friendly activities, a fantastic array of dining options and much more. Situated on Edgartown Harbor among flowering English gardens, this property is ideally located on Martha's Vineyard. Guests will enjoy watching the boats come and go as they listen to the peaceful sounds of the ocean while sitting harbor side.

5 out of 5 average rating, 8 reviews

A two-story building designed in a classic Cape Cod style is showcased, featuring a large balcony on the front. Lush green landscaping surrounds the building, enhancing the tranquil outdoor setting. Nearby structures are visible, displaying similar architectural features.

Condo in Falmouth

Beachside Villiage-Oceanfront

Located across from the popular Surf Drive Beach, Beachside Village Resort is built in true Cape Cod style all rooms being outfitted in comfortable East Coast furnishings. The beach is just a few short steps away. At Beachside Village you get the homey comfort of an East Coast Bed and Breakfast with the amenities and privacy of a resort.

4.88 out of 5 average rating, 32 reviews

An aerial view captures the expansive property nestled near the coastline. Lush greenery surrounds the home, while the blue waters of the ocean and a winding pond are visible. A sandy beach and marshy areas create a natural landscape that invites exploration.

Vacation home in Tisbury

Stunning MV Cottage on 7 acres w/ Private Beach

Enjoy nature's majesty at this classic 7 acre seaside MV escape. Sunbathe on 100 feet of private beach, explore Lake Tashmoo by kayak, read a book in the pondside hammock, have cocktails on the screened in porches, barbecue every night: make lifelong memories with your loved ones in one of the most beautiful places on earth.

4.84 out of 5 average rating, 106 reviews

Charming Falmouth Heights Steps to Beach

Prime location in Falmouth Heights!!! Steps from beloved Falmouth Heights beach, the Black Dog Café, Shipwrecked, and the finish line to the Falmouth Road Race! We are also a short walk to the Island Queen Ferry to Martha’s Vineyard, the Falmouth Yacht Club, and the delights of Falmouth’s marvelous Main Street!

A view from a window captures a quiet street lined with parked vehicles. Beyond the road, water is visible, suggesting proximity to a harbor. Green grass frames the scene, creating a sense of openness in the neighborhood.