Compare Vacation Rentals & Airbnb in Oak Bluffs, MA

This Oak Bluffs holiday home is situated a short walk from a private beach and Waterview Farms Golf Course.
The four-bedroom property sleeps eight, boasts a chef's kitchen with dishwasher, offers a garden, parking, and internet access, and includes linen service (BYOL option available); a minimum seven-night stay applies during peak season (June-September).

This Oak Bluffs holiday home is conveniently situated less than 1.6km from Oak Bluffs Harbour and Eastville Beach, and a 15-minute walk from Martha's Vineyard Hospital.
This 186 square metre property boasts three bedrooms, two bathrooms, sleeps seven guests, and includes a fully equipped kitchen, private garden with barbecue, patio, and free Wi-Fi.

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 Oak Bluffs flat offers a central location, a 15-minute walk or 5-minute drive from beaches, shops, and dining.
This family-friendly accommodation sleeps up to 8 guests across 6 beds, featuring air conditioning, Wi-Fi, a full kitchen, and an outdoor shower, with an upper-level loft providing additional living or sleeping space.

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 three-bedroom Victorian house in Oak Bluffs, bordering Sunset Lake, is less than 1 km from the town centre, harbour, and public beaches.
Sleeping eight, it offers two bathrooms, Wi-Fi, pet-friendly accommodation, and is ideally located for exploring attractions such as the Cottage Museum, Martha's Vineyard Film Center, and the Flying Horses Carousel.

This Oak Bluffs residence is located near Inkwell Beach, providing easy access to attractions such as the Flying Horses Carousel and Island Cove Adventures.
This spacious four-bedroom, five-bathroom house spans 289 square meters, accommodating up to eight guests with amenities including a deck, garden, patio, gas grill, and an on-site tennis court.

This apartment is situated in prime downtown Oak Bluffs, offering ocean views and a short walk to Circuit Avenue and Trinity Park Tabernacle, with convenient access to Oak Bluffs Harbour and Woods Hole Terminal within 1 kilometre.
This 61 square metre condominium accommodates up to six guests across two bedrooms, featuring air conditioning, Wi-Fi, a fully equipped kitchen with an oven and microwave, a fireplace, and an in-unit washer and dryer.

This central Oak Bluffs flat is a short walk from the ferry terminal and Oak Bluffs Town Beach, with Edgartown Lighthouse 10 kilometres away.
This spacious two-bedroom holiday home accommodates up to nine guests and features a fully equipped kitchen, air conditioning, a balcony with city views, a patio, and on-site laundry facilities, with free WiFi available in public areas.

This spacious apartment is located in Oak Bluffs, just a short distance from the beaches, shops, restaurants, and the airport. It has excellent user, location, and cleanliness ratings.
The property has four bedrooms and three bathrooms, offering 219 square metres of living space and comfortable accommodation for up to ten guests. The apartment features a modern kitchen, a large dining area, a private garden, a spa, and parking, making it an ideal choice for families or groups.

This three-bedroom Tisbury cottage, perfect for families, is situated a short walk from Vineyard Haven's shops, restaurants, and ferry terminal.
The 3-bedroom property boasts a spacious living room, eat-in kitchen with dishwasher, two bathrooms, a large garden with outdoor shower, and parking; it comfortably sleeps six guests and offers Wi-Fi.

This Oak Bluffs property is situated just 1.5 kilometres from the town centre and beaches, and a short walk from Farm Neck Golf Course and Land Bank walking trails. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The home features a spacious and bright open plan layout with cathedral ceilings and plenty of natural light. Guests can enjoy a fully equipped kitchen with granite countertops, stainless steel appliances, a dining room, and a large deck with a covered porch and outdoor shower, perfect for enjoying the beautiful Vineyard weather.

This three-bedroom, two-bathroom detached house offers excellent proximity to the VH Yacht Club beach, just 240 metres away, and is within walking distance to downtown Vineyard Haven, providing easy access to the ferry, shops, and cinema.
This property can accommodate up to six guests and features a fully equipped kitchen with a double oven and large fridge, central air conditioning, ceiling fans, and off-street parking.