Vacation Rentals in Oak Bluffs, MA

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.

Maushop By The Sea, a self-catering cottage in the New Seabury resort community of Mashpee, Massachusetts, is located steps from a private Maushop beach and a short walk (less than 0.8 km) from Popponesset Marketplace with its renowned Raw Bar.
This one-bedroom holiday home, sleeping up to four guests, features a sunroom, full bathroom, kitchen with dishwasher, washer/dryer, Wi-Fi, and a patio; nearby attractions include Mashpee Commons (a short drive away), the Cape Cod Children's Museum, and the Cape Cod Baseball League.

This Mashpee holiday home is situated approximately 21 kilometres from both the Sandwich Glass Museum and Heritage Museums & Gardens.
This two-bedroom, two-bathroom property offers 186 square metres of space, sleeping up to 17 guests and boasting a fully equipped kitchen, private garden, free Wi-Fi, and free on-site parking.

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 East Falmouth holiday let is located in the town centre, a single property from Great Neck Pond, offering direct water views, and is within 2 kilometres of Falmouth Village and Bristol Beach.
This spacious 104 square metre maisonette accommodates up to six guests with two bedrooms and two bathrooms, featuring air conditioning, a dishwasher, a balcony, and a garden, with dogs up to 14 kilograms welcomed.

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 spacious 272 m² holiday home in Oak Bluffs offers convenient access, being just an 11-minute drive from the Martha's Vineyard Preservation Trust Historic Buildings.
The family-friendly property accommodates up to 10 guests with 5 bedrooms and 5 bathrooms, featuring a private swimming pool, terrace with a fire pit, and a well-equipped kitchen with a dishwasher and microwave, alongside Wi-Fi and air conditioning.

This Falmouth apartment is a short walk from Falmouth Marina Park, Falmouth Harbour, and ferries to Martha's Vineyard, with beaches and the town centre a short drive away.
This 79 square metre dwelling sleeps four people and features two bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a garden, and an enclosed yard with an outdoor shower, offering easy access to local attractions and water-based activities.

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.

This East Falmouth holiday home is situated 3-16km from several beaches including Bristol Beach, Menauhant Beach, Old Silver Beach, and South Cape Beach State Park, and is also conveniently located 3km from Cape Cod Winery and 6km from Falmouth town centre.
The 65 square metre property sleeps four guests in two bedrooms and one bathroom, and boasts a fully equipped kitchen, patio with gas grill, laundry facilities, ample parking, and access to a pond, plus a Smart TV and board games.

This West Falmouth cottage is a 2-minute walk from the Shining Sea Bikeway, offering easy access to Woods Hole and ferry services, and is a short drive from multiple beaches and 2 minutes on foot from Falmouth's shops and restaurants.
The family-friendly apartment sleeps four guests in two bedrooms and one bathroom, featuring air conditioning, a fully equipped kitchen with a dishwasher, and a garden with an outdoor shower.

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.