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A historic two-story house with a balcony and a porch, surrounded by a well-maintained garden.

Photo by William Keller

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    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Oak Bluffs holiday homes

    1. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

    A circular stone patio with Adirondack chairs and a small table in a forested area.

    2. Vineyard Luxury "Yurt"

    A circular skylight with wooden beams radiating inward, a white air conditioning unit, and three circular windows with greenery views.

    3. Oak Bluffs 4BR • 5 Min Drive to Downtown

    A beach with large rocks, a sandy shore, and a cliff.

    4. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

    A covered patio with wicker furniture, a wooden deck, and a window overlooking the yard.

    5. Beautiful Estate with salt water pool & pond with kayaks

    A swimming pool with a pergola and outdoor seating area.

    6. Walk to Beach! Oak Bluffs Home & Studio

    An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

    7. New 4 BR house near center and beaches with bikes

    A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

    8. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

    A boat docked at a concrete pier with a sandy shore in the background.

    9. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

    A single-story house with a front porch, a garage, and a fenced backyard.

    10. Coastal chic meets French Provençal in this newly renovated oceanfront home.

    A large, two-story house with a garage, a well-maintained lawn, and a view of the ocean.

    11. The Seashell Cove - Martha's Vineyard

    A wooden deck with a table and chairs, surrounded by lush greenery.

    12. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

    A beach with clear water and a sandy shore.

    13. Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

    A covered outdoor seating area with a ceiling fan, cushioned seating, and curtains.

    14. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

    A wooden deck with a table and chairs, a sliding glass door, and a grill area.

    15. Spacious 5BR Falmouth Family Retreat with Deck, Ping Pong Table & Central A/C

    A two-story house with a front porch, a well-maintained lawn, and mature trees in the background.

    16. Nice home near Mashpee Commons and all Falmouth has to offer

    A modern kitchen with white cabinets, a dining table with chairs, and a view of the outdoors.

    17. Backyard Retreat / 5 Min > Beach & Main St

    A residential street with houses, a speed limit sign, a utility pole, and a clear sky.

    18. Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!

    An aerial view of a large house with a swimming pool, a tennis court, and a well-maintained lawn.

    19. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

    A patio with outdoor furniture, a tree, and a lattice fence.

    20. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

    A kitchen with a dining area, a ceiling fan, and a view to an outdoor patio.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Oak Bluffs

    The colourful gingerbread cottages of the Martha's Vineyard Campground will charm you with their whimsical Victorian details. Take the Flying Horses carousel for a spin, then stroll along Ocean Park's waterfront where locals gather for sunset picnics.

    See all hotels in Oak Bluffs

    A historic two-story house with a balcony and a porch, surrounded by a well-maintained garden.

    Photo by William Keller

    Top reviews in Oak Bluffs

    Morgan Hotel

    A modern living room with a sofa, armchairs, and a coffee table. A neon sign with the name "MORGAN" is visible on the wall.

    Mansion House Inn And Spa

    A marina with boats docked along the shore, surrounded by greenery and a sandy beach.

    Vineyard Harbor Motel - Private Beach

    Beach

    The Coonamessett

    A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

    Shore Haven Inn

    A large, multi-story house with a covered porch and a well-maintained lawn.

    Faraway Martha's Vineyard

    A two-story building with a symmetrical facade, featuring a central entrance with a green door, flanked by windows with green shutters.

    The Lightkeepers Inn

    A residential property with a gravel driveway, a wooden bench, and a house with a shingled exterior.

    Inn on the Sound

    A wooden deck with a white umbrella, two blue lounge chairs, and a view of the ocean.

    Frederick William House

    A two-story house with a stone facade, a balcony, and a well-maintained garden.

    Lamberts Cove Inn

    A wooden deck with Adirondack chairs and a pergola.

    AutoCamp Cape Cod

    A spacious outdoor seating area with sofas and chairs, a central table, and a view of the landscape.

    The Palmer House Inn

    A rocky beach with people relaxing and fishing.

    The Club at New Seabury

    A row of white lounge chairs with blue cushions, arranged under a white canopy, overlooking the sea.