Compare Vacation Rentals & Airbnb in Oak Bluffs, MA

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.

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 four-bedroom house in Edgartown, Martha's Vineyard, is centrally located on a 0.2-hectare plot, offering privacy and convenient access to Edgartown centre, Oak Bluffs (approximately 6.4 kilometres away), and Vineyard Haven (approximately 7.2 kilometres away), with a state beach just 5.6 kilometres distant.
This property accommodates up to ten guests with a king bed, queen bed, four twin beds, and a futon, featuring three bathrooms, air conditioning, and Wi-Fi, and is situated near Inkwell Beach, the Vincent House Museum, and the Flying Horses Carousel.

This Falmouth flat is less than 1.6km from Main Street and Cape Cod beaches, and within a 24km radius of the Falmouth Museums on the Green and the College Light Opera Company.
The one-bedroom, one-bathroom apartment sleeps six, offering air conditioning, Wi-Fi, a hair dryer, iron and ironing board, and is ideally located for exploring Falmouth's attractions and enjoying nearby shops and restaurants.

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 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 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.

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 Heights family-friendly yacht, situated in the Historic District, is steps from the Black Dog Café, 0.48km from Heights Beach, and an 8-minute walk from the Island Queen Ferry.
Sleeping up to 11 guests in six bedrooms across three levels, this 1893 gingerbread-style house boasts two bathrooms, a fully equipped kitchen, a large garden with a 7.6m rope swing, and beach equipment; owners provide a personal welcome.

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.

Maushop By The Sea, a self-catering property in Mashpee, Massachusetts, is located 2.1km from South Cape Beach and 4.7km from South Cape Beach State Park, offering easy access to the coastline and within a 24km radius of attractions such as the Sandwich Glass Museum and Heritage Museums & Gardens.
This one-bedroom house, sleeping seven guests, boasts a 54 square metre floor area, a fully equipped kitchen with dishwasher and coffee machine, a private garden, free Wi-Fi, and is near a children's playground and cycling routes.

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.