Oak Bluffs, MA Vacation Homes from ￥24,655

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Our top choices for Oak Bluffs vacation homes

A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

1. Vineyard Luxury "Yurt"

Oak Bluffs

David C.

￥77,088 total

includes taxes & fees

Nov 16 - Nov 17

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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

Oak Bluffs

Chris S.

￥112,112 total

includes taxes & fees

Nov 20 - Nov 21

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

3. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

￥99,940 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

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

Oak Bluffs

"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...

Kate K.

￥144,922 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Oak Bluffs

Lamar A.

￥492,085 total

includes taxes & fees

Nov 30 - Dec 1

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

6. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

￥136,215 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Katama

Susan M.

￥264,118 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Seconsett Island

Michele M.

￥69,198 total

includes taxes & fees

Nov 10 - Nov 11

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

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

Falmouth

Stephanie B.

￥82,891 total

includes taxes & fees

Nov 10 - Nov 11

A covered outdoor seating area with a view of the ocean, a ceiling fan, and a flat-screen TV on the wall.

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

East Falmouth

Ben L.

￥152,941 total

includes taxes & fees

Nov 19 - Nov 20

A spacious living area with wooden beams, a dining table, and a sofa.

11. The Seashell Cove - Martha's Vineyard

Katama

Eric C.

￥168,702 total

includes taxes & fees

Nov 10 - Nov 11

A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

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

Falmouth

Kelsey B.

￥124,790 total

includes taxes & fees

Dec 1 - Dec 2

A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

13. West Falmouth Family Retreat Near Chapoquoit Beach

Falmouth

￥162,539 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck overlooking a calm lake with trees and houses in the background.

14. Stunning 4-bedroom Private Fresh Water Beach Front

East Falmouth

Kathryn C.

A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

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

Fairhaven

￥90,381 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Sandwich

￥59,130 total

includes taxes & fees

Nov 10 - Nov 11

A backyard with a pool, lounge chairs, a fire pit, and string lights along the fence.

17. Pool Escape in East Falmouth

East Falmouth

Gloria C.

￥198,558 total

includes taxes & fees

Nov 10 - Nov 11

A wooden deck with a table and chairs, overlooking a body of water and trees.

18. Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Barnstable

Molly R.

￥175,715 total

includes taxes & fees

Nov 10 - Nov 11

A water park with a large central pool, multiple slides, and a variety of play structures.

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

Fairhaven

Lauren F.

￥75,589 total

includes taxes & fees

Nov 30 - Dec 1

A beach with sand, flowers, and a clear sky.

20. Sal's Place

Hyannis

￥64,363 total

includes taxes & fees

Nov 10 - Nov 11

View all properties

Learn more about Oak Bluffs

The colorful 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.

Top reviews in Oak Bluffs

A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

Madison Inn

Oak Bluffs

10/10 Excellent

Anonymous traveler

A spacious living room with a sofa, chairs, a coffee table, and a staircase.

Morgan Hotel

Oak Bluffs

10/10 Excellent

Raymond

A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.

Vineyard Harbor Motel - Private Beach

Vineyard Haven

10/10 Excellent

Martina

A cozy room with wicker furniture, a stone fireplace, and a view of the ocean.

Inn on the Sound

Falmouth Heights

10/10 Excellent

Lisa

A multi-story hotel with a grand entrance, a flagpole, and a well-lit facade.

Vineyard Square Hotel & Suites

Edgartown

10/10 Excellent

Lynn

A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

Faraway Martha's Vineyard

Edgartown

10/10 Excellent

Cathy

An outdoor patio with a fire table, seating, and a table set for a meal.

The Palmer House Inn

Falmouth

10/10 Excellent

My husband and I loved our stay at the antiques-filled Palmer House Inn. We were able to easily walk to the active Main Street and had our choice of excellent restaurants and gift shops to browse. We also walked to the beach (mostly sandy, but with many sharp rocks as you enter the water), rented bikes and rode to a lighthouse, and enjoyed the delicious breakfasts while sitting on the porch in the cooler weather. I would definitely recommend this property to anyone heading to Cape Cod.

Lori

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

Shore Haven Inn

Falmouth

10/10 Excellent

Nicole

A spacious living area with a dining table, sofas, and a view of the sea.

Harbor View Hotel

Edgartown

10/10 Excellent

Anonymous traveler

A cozy living room with a fireplace, comfortable seating, and a bookshelf.

The Ashley Inn

Edgartown

10/10 Excellent

Anonymous traveler

A bedroom with a bed, two bedside lamps, a window, and a framed picture on the wall.

The Lightkeepers Inn

Edgartown

10/10 Excellent

Anonymous traveler

A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

The Franklin Hotel Martha's Vineyard

Edgartown

10/10 Excellent

Kathryn

Red Horse Inn

Falmouth Heights

10/10 Excellent

Meredith

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

Frederick William House

Falmouth

10/10 Excellent

My friend and I spent 4 nights in this beautiful bed and breakfast. The property is conveniently located on Route 28 in Falmouth. Not only is the house on a bike trail, but you are allowed to use the bikes for free, even to take to the Vinyard, a 40 minute ride by ferry. We went over twice using the Queen Authority first from Falmouth and the Steamship Authority from Woods Hole the next. The Steamship was cheaper and better. But there are really nice beaches nearby. Woods Hole is nearby where...

Elm