Waterfront holiday rentals in Dukes County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Dukes County

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 112 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

4.96 out of 5 average rating, 26 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.

Superhost

Home in Oak Bluffs

4.95 out of 5 average rating, 19 reviews

Coastal Chic Cape Centrally Located Oak Bluffs, MA

Charming coastal Cape centrally located and privately situated on 1.3 acres of lush land. Sleeps up to 6 guests comfortably. Open living/dining, hardwood flooring, cathedral ceilings, stainless appliances, island eatery, dining for 6. Deck with views of the duck pond, outdoor seating, dining and BBQ grill. Living room with comfortable wrap around couch and large flatscreen TV. 2 Full bathrooms with shower/tub combo. Bedrooms: Primary; King Guest 2xDoubles Loft; Double Bungalow; Queen

Guest favourite

Rental unit in Tisbury

4.93 out of 5 average rating, 120 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

Rental unit in Falmouth

4.9 out of 5 average rating, 78 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.

Guest favourite

Cottage in Tisbury

4.98 out of 5 average rating, 43 reviews

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

Superhost

Home in Oak Bluffs

4.82 out of 5 average rating, 188 reviews

Waterview, Private, Walk to Beach, Mile to Town

Ask the host about ferry reservations if they appear to be sold out! Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing.

Guest favourite

Guest house in Oak Bluffs

4.98 out of 5 average rating, 60 reviews

Coastal Bungalow

Discover this newly renovated property located just minutes from downtown on the Lagoon. The rental sits separately behind the main house in what once held a media room, lovingly converted to an open concept guest suite with queen bed, kitchenette, bath, and living space with convertible sleeper sofa. USB charging bedside lamps are some of the amenities offered. Accommodates 2 guests and possible 1-2 children. Private beach access on the Lagoon and 5 minutes from town.

Guest favourite

Guest house in Tisbury

4.97 out of 5 average rating, 72 reviews

King bed, Stunning Water Views,AC,Near Bike Path

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

Apartment in Oak Bluffs

4.75 out of 5 average rating, 12 reviews

Ocean View Gem, Walk to it All, No Car Needed!

Martha’s Vineyard vacationers dream! Enjoy walking everywhere from this recently renovated condo with private balcony and spectacular ocean views: Inkwell Beach, Circuit Avenue, Linda Jeans, OB ferry and harbor, Campground Cottages, Tabernacle, Illumination, shops, restaurants and more! No car needed. Lovely 2 BR/1 BA condo sleeps up to 4 guests. Amazing location with spectacular views! Experience island living at its finest.

Guest favourite

Townhouse in Edgartown

4.98 out of 5 average rating, 40 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

Rental unit in Oak Bluffs

4.88 out of 5 average rating, 152 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)