Waterfront holiday rentals in Dukes County

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Top-rated waterfront rentals in Dukes County

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

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Guest favourite

Home in Edgartown

4.83 out of 5 average rating, 69 reviews

Spacious, Old Vineyard charm with Private Beach

This is a classic, rare vintage Vineyard property: a beautifully simple, comfortable, and charming family house located directly on its own private beach on Katama Bay. Peaceful and secluded, yet a short walk or bike ride to the popular, public surf beach, and 3 miles from bustling, historic Edgartown. The house is both intimate and expansive: equally perfect for small families or larger groups, for quiet retreats or festive reunions. Spacious and soulful indoors and out. A magical refuge. .

Top guest favourite

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 116 reviews

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

Guest favourite

Home in Chilmark

4.97 out of 5 average rating, 32 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

This authentic beach cottage is centrally-located in the fishing village of Menemsha with stunning views of the sunset, the harbor, the beach and Menemsha Creek. Charter a fishing boat in the harbor across the street or spend the day on the beach just a few steps away. As you meander back to the house, pick up fresh fish to grill on the deck or pre-cooked lobsters and steamers. If you prefer to eat out, rinse off in the outdoor shower and take a walk around the corner to dinner with a view.

Guest favourite

Flat in Falmouth

4.89 out of 5 average rating, 84 reviews

On Eel Pond: Woods Hole Waterfront Retreat

Enjoy a different pace of life in the village of Woods Hole. Situated on Eel Pond, this charming 3rd floor apartment overlooks the pond, with Water Street and Vineyard Sound beyond. You can walk to everything, or just relax in the Adirondack chairs along the seawall. You are a short walk from the ferry to Martha's Vineyard, the Shining Sea Bikeway, and only 1/3 mile to Stoney Beach. A perfect opportunity for relaxation and activity, along with excellent dining options and fresh ocean breezes.

Top guest favourite

Flat in Tisbury

4.92 out of 5 average rating, 130 reviews

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

Guest favourite

Townhouse in Edgartown

5 out of 5 average rating, 8 reviews

Bright townhome with private ponds, pickleball

Beautifully furnished condo is centrally located in a park-like setting. This property is perfect for anyone who loves to explore the outdoors or just relax on the private deck at home. The Sengekontacket Assoc. in Oak Bluffs is a desirable waterfront community easily located off the bike path and on the bus route to town. Private amenities include a freshwater pond just 2-min walk down a quiet road; a large saltwater pond about a 10-min walk to a community dock; and tennis/pickleball courts.

Top guest favourite

Flat in Falmouth

5 out of 5 average rating, 23 reviews

Peaceful Pond view apartment close to beach

Nestled in nature, minutes from Falmouth and Woods Hole. Relax in this tranquil setting looking over Oyster Pond. Enjoy the view from deck, take a paddle on the pond. While apartment is in home of owner there is a private living room, and separate bed/bath and own entrance. Queen bed with linens. Limited cooking with microwave mini fridge and outdoor grill. All rooms with views of pond, it will be hard to leave this peaceful setting! Falmouth has dining, beaches and nightlife.

Guest favourite

Guest house in Tisbury

4.98 out of 5 average rating, 80 reviews

King bed, Water Views,AC,Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay.

Superhost

Cottage in Chilmark

4.88 out of 5 average rating, 8 reviews

Chilmark, Martha' s Vineyard Water View Cottage

Topside is a lovely one 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.

Guest favourite

Townhouse in Edgartown

4.98 out of 5 average rating, 47 reviews

Surf and Turf Townhouse

Cozy 2 bdr, 1.5 bath townhouse perfect for a family of four looking for an action-packed Martha's Vineyard vacation. We are located right between Oak Bluffs and Edgartown offering easy access to all down-island towns and bike paths. The development provides access to dock on Sengekontacket (where you'll find our two kayaks) a freshwater pond, and tennis/pickle ball courts for you to enjoy.

Superhost

Flat in Oak Bluffs

4.88 out of 5 average rating, 155 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

3rd fl Waterfront Oak Bluffs Harbor Penthouse- Sleeps 2 comfortably-3 in a pinch. (356sqft) . Queen bed & a reclining futon couch. With kitchenette & amazing harbor views, you cannot get closer to harbor, unless you fell in. Located above a seasonal restaurant, with 5 open air restaurants (2 on each side, & were in the middle with our restaurant Lobsterville Bar & Grille below)

Guest favourite

Home in Chilmark

4.87 out of 5 average rating, 55 reviews

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.