Search accommodations in Oak Bluffs, MA

Winnetu Oceanside Resort at South Beach in Edgartown, Massachusetts enjoys an oceanfront location on South Beach, a short distance from Edgartown's town centre and its historic sites.
The resort offers comfortable lodgings with selected rooms including towels, promising a relaxing stay near Edgartown's shops, restaurants, and various attractions.

This custom-built estate in Oak Bluffs, due for completion in May 2026, offers a private retreat with convenient access to local attractions.
This luxury residence sleeps eight and features a main house with three bedrooms and 3.5 bathrooms, alongside a separate one-bedroom, 1.5-bathroom guest home, complete with a heated swimming pool, hot tub, and extensive grounds.

This stylish five-bedroom house in Upper Makonikey, West Tisbury, is a five-minute walk from private association beaches and a 1.6-kilometre drive from West Tisbury's town centre.
Offering a private pool with Vineyard Sound views, this three-acre property sleeps ten guests and features three bathrooms, a fully equipped kitchen, and ample parking; nearby amenities include a tennis court.

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 Katama holiday home is situated within 3.2km of Edgartown's Old Whaling Church, Vincent House Museum, and Public Library, and within 4.8km of Katama Plains and Lighthouse Beach.
This spacious 4-bedroom, 4-bathroom property sleeps 8 guests and boasts a fully equipped kitchen, private patio, garden, spa, and parking; DVD player and barbecue grills are also available.

This Oak Bluffs holiday home is centrally located, a short walk from Circuit Avenue, Ocean Park, the Cottage Museum, and within 0.8 km of Trinity Park Tabernacle and the Flying Horses Carousel.
This five-bedroom property boasts 279 square metres of floor space, sleeps up to 10 guests, and includes a fully equipped kitchen, a jacuzzi, a terrace, a garden, a spa, a fitness centre, and free Wi-Fi; nearby activities include the beach and various historical sites.

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 Oak Bluffs holiday home is situated within 5km of Farm Neck Golf Club, Gus Ben David's World of Reptiles and Birds Park, and Oak Bluffs Public Library, offering easy access to Circuit Avenue and Trinity Park Tabernacle.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a Jacuzzi, tennis court, private garden with barbecue, in-unit laundry, and smart TV, alongside a fully equipped kitchen and air conditioning.

This apartment in Oak Bluffs offers a prime location, just a short walk to Inkwell Beach, Ocean Park, and the Flying Horses Carousel, with local amenities and the ferry to Nantucket also within an 800-1000 meter stroll. This property accommodates up to eight guests with four bedrooms and two bathrooms, featuring complimentary Wi-Fi, a fully equipped kitchen, air conditioning, and parking for three cars.

This two-bedroom cottage is located on a quiet private road in Oak Bluffs, within 1 kilometre of Circuit Avenue and Main Street shops, restaurants, and the historic Flying Horses Carousel.
This 69 square metre dwelling accommodates up to six guests, featuring a fully equipped kitchen with stainless steel appliances, air conditioning, Wi-Fi, a wraparound deck, private patio with an outdoor fire pit, and private parking.

This waterside flat in Oak Bluffs is located on Brush Pond, offering views of Lagoon Pond and Vineyard Sound, and is within 1.6 kilometres of the Oak Bluffs Steamship Authority and Oak Bluffs Town Beach.
This 77 square metre apartment sleeps four guests, featuring two bedrooms, one bathroom, a full kitchen with a dishwasher, air conditioning, a terrace, a garden, an outdoor shower, and a private washer and dryer, with the Flying Horses Carousel a few blocks away and Joseph Sylvia State Beach 6.4 kilometres distant.

This Oak Bluffs holiday home is less than 1.6km from the beaches and a 15-minute walk from Oak Bluffs Town Beach, with Martha's Vineyard Airport 8km away.
The 102 square metre property offers two bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, air conditioning, free Wi-Fi, parking, and a garden.

This Oak Bluffs studio apartment, situated in a converted barn a short distance from Oak Bluffs' beaches and attractions, offers a unique setting.
The open-plan self-catering unit sleeps up to four guests, featuring a queen bed, a full-size pull-out sofa, a kitchenette with a fridge, air conditioning, and access to a shared patio; parking is also available.

This charming cottage is situated in a peaceful part of Oak Bluffs, just 0.8km from the beaches, shops, and restaurants, making it a convenient base for exploring the town. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage offers two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the private hot tub, outdoor shower, and fully equipped kitchen, along with a relaxing patio for enjoying the garden.

This Oak Bluffs holiday home is situated a short walk (under 1.6km) from Eastville Beach and Martha's Vineyard Hospital, and less than 1.6km from East Chop Lighthouse and the Oak Bluffs Public Library.
The 130 square metre property boasts four bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, terrace, garden, parking, and free Wi-Fi.

This Oak Bluffs apartment is conveniently located just 0.5 km from the ferry, beaches, and public transport, making it easy to explore the island's attractions. The apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment has three bedrooms and can accommodate up to eight guests, making it ideal for families or groups of friends. The apartment features a fully equipped kitchen, air conditioning, a garden, and parking, along with a welcome package that includes beach towels, sunscreen, and other essentials.