Beachfront holiday rentals in Dukes County

Serenity on Martha's Vineyard

This 2BR, 2 Full Bath Condo with air condition (AC) and elevator access is located across the street from State Beach (AKA the "Ink Well") in Oak Bluffs. It's on the top floor, recently redecorated, with all the amenities for a wonderful vacation. Both bedrooms have Smart TVs & AC. Free Wi-Fi. Great location, within walking distance to the ferry, beach and downtown Oak Bluffs, restaurants and shops. Car not needed! Get ready to relax and unwind. It's the perfect location! Welcome to Serenity!

Oceanfront cottage on Surf Drive beach in Falmouth

Smell the salty air and listen to the sounds of the ocean from this renovated charming cottage - just cross the street to the beach! This 3BR, 2BA has kitchen, LR, bedrooms with sliders to patio. Home has gorgeous water views of Martha's Vineyard. 1 mile to town center with restaurants & shops, less than a mile to Shining Sea bikeway. This is a premier location in beautiful Falmouth! Please note that summer rentals are a 7-night minimum, most weeks with Saturday check-in / check-out.

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.

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Enjoy one of THE most desirable locations on the Vineyard! Enjoy AMAZING sunrises & SPECTACULAR ocean views from this family-run, premier top floor condo. Across street from popular town beach, short walk to Ocean Park, Waban Park, Flying Horses, Steamship Authority & downtown Circuit Ave (restaurants, shops). Bring a car (one unreserved parking spot available) or walk over from boat. Bike delivery & storage available. Linens, beach towels & chairs provided. Island Paradise! ☀️🏖️

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!

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

Spacious 2 BR Cottage, Ocean View, Path to Beach

Forecastle is a two bedroom and one bath, full kitchen, living room with wood burning fireplace and Roku TV. It includes a private deck with chairs and a screened-in porch with a picnic table. Additional amenities include outside showers, BBQ grill, use of the inn's facilities, and walk-on or car passes to a choice of Chilmark's Private Beaches - Lucy Vincent or Squibnocket during beach pass season.

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.

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.

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.

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.

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!