Waterfront holiday rentals in Oak Bluffs

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Top-rated waterfront accommodation in Oak Bluffs

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Guest favourite

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 101 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

18–25 Apr

$802 NZD per night

Superhost

Home in Oak Bluffs

4.82 out of 5 average rating, 179 reviews

Waterview, Private, Walk to Beach, Mile to Town

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. Please view our entire listing and reviews for more about our unique property.

23–30 May

$999 NZD per night

Guest favourite

Townhouse in Edgartown

4.97 out of 5 average rating, 33 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. PLEASE NOTE: In high season (late June to Labor Day,) we can only accept Saturday to Saturday requests.

4–11 Sep

$840 NZD per night

Guest favourite

Home in Fairhaven

4.95 out of 5 average rating, 146 reviews

Drop Anchor Waterfront

Drop Anchor at this quiet retreat. Have coffee in your rocking chair overlooking your waterfront escape. Enjoy drinks on a gracious sun terrace perched above your own private beach. Flip through a magazine in your waterside summerhouse. Outdoor showers. Water toys. Kayaks & fishing poles available upon request. ..All that before you've even set foot in a lovingly appointed home with large dining table, big screen TVs, fireplace. Moments from sandy town beaches or ferry ride to the islands.

3–8 May

$821 NZD per night

Guest favourite

Condo in Oak Bluffs

4.95 out of 5 average rating, 21 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Stay in one of the most desirable locations on the Vineyard! Enjoy amazing sunrises & SPECTACULAR ocean views from this family-run, premier top floor (3 of 3) condo. Across street from popular town beach, short walk to Ocean Park, Waban Park, Flying Horses, Steamship Authority & downtown Circuit Ave (restaurants, shops). Bring your car (one unreserved parking spot available) or walk over from boat. Bike delivery & storage avail. Bed linens & towels are included. We hope to accommodate you!!

22–29 Sep

$1,526 NZD per night

Guest favourite

Cottage in Falmouth

4.94 out of 5 average rating, 135 reviews

“Cozy Cottage” on Great Bay

Due to the coronavirus, we’re taking extra care to disinfect frequently touched surfaces between reservations.” Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach.We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.

12–19 Oct

$381 NZD per night

Guest favourite

Apartment in Tisbury

4.92 out of 5 average rating, 102 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, the 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! The new Martha's Vineyard Museum is a five minute walk, down the same street. My place is great for couples and solo adventurers.

5–12 Jun

$452 NZD per night

Guest favourite

Cottage in Sandwich

4.95 out of 5 average rating, 159 reviews

Waterfront Lake Cottage, Private Beach, Wow View!

Wake up to a magnificent view of a beautiful lake with waves lapping gently below your window! Guests love this stylish and open designed home dramatically located on the shores of a large, recreational lake. It's like being on your own luxury houseboat! Enjoy the wall-to-wall windows with a panoramic view, a beautiful new modern kitchen, your own private beach, a new luxurious King hybrid gel/coil bed, private office space, large bathroom with curved shower, and much more!

26 Feb – 5 Mar

$759 NZD per night

Guest favourite

Guesthouse in Oak Bluffs

5.0 out of 5 average rating, 48 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.

7–14 May

$904 NZD per night

Superhost

Cottage in Fairhaven

4.8 out of 5 average rating, 279 reviews

On the Beach Cottage in Fairhaven

Enjoy your own private beach at our comfortable Beach Cottage. Hop on the local bike rentals to the nearby soda shop for snacks and treats. Or throw a line in for the days fresh catch. Spend some time relaxing on the back deck overlooking the saltwater marsh. After a day of searching for Sea glass and building sand castles on your own beach you will fall right asleep to the sounds and smells of the ocean right outside your bedroom patio doors. Welcome to your vacation

8–15 Oct

$519 NZD per night

Guest favourite

Apartment in Oak Bluffs

4.88 out of 5 average rating, 146 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 4 open air restaurants (2 on each side) Guests must bring they’re own LINENS and TOWELS. Bed is queen. There is a futon reclining couch that could be slept on, but I’d prefer not to have it used that way.

15–22 Sep

$744 NZD per night

Guest favourite

Home in Falmouth

5.0 out of 5 average rating, 135 reviews

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

2–9 Nov

$738 NZD per night