Compare Vacation Rentals & Airbnb in Oak Bluffs, MA

Captain Blake Adams' historic 1881 whaling captain's residence in West Tisbury offers a unique stay, situated within easy walking distance of Alley's General Store and 7A, and boasting private access to Lambert's Cove beach.
This restored holiday home accommodates up to 10 guests, featuring air conditioning, three bathrooms, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, with excellent bus links for island exploration.

This Falmouth, Cape Cod holiday home is conveniently located near Green Pond, 9.6km from Menauhant, 12.8km from Surf Drive, and 22.4km from Old Silver Beach.
This two-bedroom, one-bathroom property sleeps four, boasting a private 688 sq m plot with an outdoor shower, BBQ, firepit, two TVs, a gas fireplace, and an outdoor fireplace with a TV; in-unit laundry and Wi-Fi are included.

Winnetu Oceanside Resort at South Beach is situated near South Beach in Edgartown, Massachusetts, a short 5.1 km walk from the beach and 5.1 km from Edgartown's Main Street.
The resort, offering studios to four-bedroom suites, some with kitchenettes, boasts seasonal heated pools, a health club, a children's program, tennis courts, The Dunes restaurant with ocean views, and arranges clambakes, lighthouse tours, and kayak trips.

This East Falmouth cottage is located 6.4 kilometres from Bristol Beach and offers proximity to Cape Cod attractions within a 17.7 to 46.7 kilometre radius.
This property provides accommodation for up to seven guests with two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher and oven, air conditioning, complimentary Wi-Fi, private parking, and a deck overlooking a private pond.

This five-bedroom, four-bathroom house in Katama, Edgartown, is situated a 4.8km drive from Edgartown town centre, known for its historic architecture and shops, and a short walk or cycle from South Beach.
The property boasts a private beach on Katama Bay, a spacious open-plan living area, a newly renovated kitchen with dishwasher, and features including a Weber gas grill, outdoor shower, private wood pier, and rooftop deck with sunset views; sleeping up to eight guests.

This expansive five-bedroom, four-bathroom holiday home, accommodating up to ten guests, is situated on the northern edge of Manuel F. Correllus State Forest, offering convenient access within 6 kilometres of Oak Bluffs and its shops, waterfront dining, and beaches, as well as being 6 kilometres from Vineyard Haven and 8 kilometres from Edgartown.
Guests can enjoy a private heated outdoor swimming pool, a spacious terrace and garden, a foosball table for entertainment, a fully equipped kitchen with a dishwasher, an outdoor shower, and driveway parking for six vehicles, with the property being a 6-kilometre drive from Oak Bluffs Town Beach.

This accommodation is situated in Teaticket, Falmouth, a 19-minute walk from Bristol Beach and 750 meters from the water.
This 92 square meter house offers 3 bedrooms, a fully equipped kitchen with a dishwasher, air conditioning, and a patio with an outdoor dining area, suitable for up to 11 guests with on-site cycling and a children's playground available.

This Oak Bluffs apartment is centrally located, a short walk from Inkwell Beach and just steps from the Flying Horses Carousel and Back Door Donuts.
The one-bedroom flat sleeps four, boasting a fully equipped kitchen with dishwasher, modern amenities including fast Wi-Fi and a washer/dryer, plus comfy sleeper sofas.

This Falmouth apartment is less than 2km from Main Street and Cape Cod beaches, and within a 15-minute drive of the Falmouth Museums on the Green and the College Light Opera Company.
The one-bedroom flat sleeps five, includes air conditioning, Wi-Fi, and amenities such as a hairdryer and iron, offering a convenient base for exploring Falmouth's attractions.

This Falmouth cottage, near Woods Hole, offers easy access to the Martha's Vineyard ferry (minutes away) and the Shining Sea Bike Path.
The self-catering property sleeps two in one bedroom with a king-size bed, boasting a full kitchen, a shared saltwater pool (June-September), and on-site parking.

The Cygnet, a Falmouth holiday home, is a seven-minute walk from Surf Drive Beach and within 19-34 kilometres of attractions including the Sandwich Glass Museum, the John F. Kennedy Hyannis Museum, and Heritage Museums & Gardens.
This 79 square metre property offers two bedrooms, one bathroom, sleeps seven guests, and includes a fully equipped kitchen with oven, microwave, and washing machine, plus an on-site restaurant and children's playground.

This spacious five-bedroom residence, situated in the private Fresh Pond Estates of Oak Bluffs, offers direct access to a freshwater pond and is conveniently located 3.2 kilometres from Oak Bluffs centre, 152 metres from a bike path, and a five-minute drive from Edgartown and Vineyard Haven.
This family-friendly holiday home, covering 418 square metres and accommodating up to 12 guests, boasts a heated saltwater pool, Jacuzzi, outdoor kitchen, two fully equipped kitchens including a commercial-grade one, and ample outdoor space with a 21-metre deck perfect for enjoying the surroundings.