Historic Oak Bluffs Cottage – Porch with View

Exterior view of a multi-story white house with dark roofing, gabled dormers, upper balconies, and a gravel walkway leading to a covered porch entry.

A covered front porch with dark wood flooring, white rocking chairs with striped cushions, and small side tables overlooking a neighborhood street.

Living room with a stone fireplace, wood floors, a flat-screen television, a large coffee table, and various armchairs and a sofa.

Living room with hardwood floors, a teal sofa, vintage armchairs, and a marble-topped coffee table.

Kitchen dining corner with a small wooden table, two chairs, stainless steel refrigerator, and wall shelf with metal pots.

Close-up view of a kitchen area featuring a stainless steel refrigerator, an electric stove, dark upper cabinets, and decorative kitchenware.

A kitchen with white countertops, dark blue and white cabinetry, a sink, small appliances, and a washing machine next to a window.

A kitchen with white walls, black and white cabinets with glass doors, countertop appliances, a sink, and a dishwasher.

Kitchen with white cabinetry, a sink, an exterior door, a tiled floor, and laundry appliances including a dryer topped with coffee makers.

Dining room with a table covered in a light blue cloth surrounded by wooden chairs on hardwood floors.

Dining room with a table covered in a light blue cloth, wooden chairs, a brass chandelier, and built-in white cabinets full of dishware.

Bathroom with a clawfoot bathtub, blue and white striped shower curtain, white vanity sink, and toilet.

Bathroom showing a sink and bathtub with a blue and white striped shower curtain.

A corner seating area with a red velvet chaise lounge, decorative pillows, a small side table, and a window.

A cozy sitting corner featuring a tall wicker chair with an ottoman, a wooden side table with books, a small upholstered chair, and sheer curtains over a window.

Covered porch with white rocking chairs and a safety gate looking out at a neighborhood street.

Covered porch with white rocking chairs, wicker furniture, and potted plants.

View from a porch overlooking lush green bushes, a street, and neighboring historic-style houses under an overcast sky.

A covered outdoor front porch with potted plants, an exterior wall lantern, and views of a lush green lawn and neighborhood houses.

Exterior front view of a multi-story white house with upper balconies, a screened porch, front steps, and a pea gravel walkway.

Bedroom with a white-quilted bed, wooden headboard, window with an air conditioner, and vintage dresser.

Bedroom with a white comforter on a bed featuring an ornate carved headboard, beside a white wicker accent chair and a small nightstand with a lamp.

Bedroom with a sloped ceiling, striped accent wall behind the bed, a white wicker armchair, and glass doors with floral curtains.

Bedroom with blue walls, sloped ceiling, white wicker loveseat, and double doors opening to a small balcony overlooking a street.

Bedroom with floral wallpaper, two wooden twin beds with pink bedding, and a wooden nightstand in between.

Bedroom with floral wallpaper, twin beds topped with pink gingham blankets, a rustic wooden dresser, and a ceiling fan.

Bedroom with floral wallpaper and sloped ceilings showing an open screen door leading to a small balcony overlooking greenery.

Elevated view from a balcony overlooking a residential street with Victorian-style houses, lawns, trees, and water visible in the distance under an overcast sky.

A narrow upper-level hallway with white paneled walls, framed artwork, patterned rug runners, and a staircase leading down.

A long interior hallway with white plank ceilings, an exposed brick pillar, a red patterned runner rug, and a striped settee with pillows.

Bedroom with two beds made with pale yellow bedding, a ceiling fan, a vintage dresser with an oval mirror, and a door with a window curtain.

Bedroom with two twin beds dressed in yellow quilts, an antique dresser with an oval mirror, a ceiling fan, and light yellow walls.

Bedroom with two twin beds made up with white sheets and light yellow blankets, flanking a small nightstand with a lamp.

Enclosed shower stall with textured glass door next to a window with lace curtains and patterned rugs on a wood floor.

A cozy room corner with sloped ceiling, rocking chairs, framed artwork, and a red washstand.

Narrow bathroom with white vanity, toilet, lace window curtains, and striped rug.

A paved coastal street bordered by green lawns, trees, and houses leading toward the ocean in the distance under a blue sky.

Exterior of a two-story white house with an enclosed porch, upper-level balconies, and green shrubs on a sunny day.

Street view looking down a coastal road toward the water with nearby historic houses and a fire hydrant.

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House in Oak Bluffs, Massachusetts

8 guests • 4 bedrooms • 6 beds • 2 full baths

5.00

• 3 reviews

Step into the charm of a bygone era at this classic Oak Bluffs home, filled with antiques, Persian rugs, and vintage character. From the front porch, you can take in views of the pier while rocking in the chairs, enjoying the same simple pleasures that have made this neighborhood a beloved summer destination for generations. This is not a modern, luxury home—it’s a historic Vineyard cottage, complete with creaky floors, unique décor, and plenty of personality. It’s the perfect setting for families and groups who want a comfortable, lived-in space with history at its heart. Inside the home you’ll find the following: Spacious living areas decorated with antique furnishings, including a red velvet camel-back sofa, pink chesterfield, striped chairs, and a striped settee. Air conditioning in most rooms to help keep things cool during summer days. Dining options with a six-seat dining table and a two-seat dinette in the kitchen. Full kitchen with a stainless steel stove, refrigerator, dishwasher, and all the essentials. Family room with two couches and a brand-new 50" TV for downtime. Bedrooms (all with new mattresses): Primary suite: King bed, hardwood floors, dresser, wicker sofa, and a private balcony. Second bedroom: Queen bed with a rocking chair and Persian rug. Two additional bedrooms: Each with two twin beds—great for kids or extra guests. Two full bathrooms plus an outdoor shower. Extras for your stay: Washer and dryer Free WiFi and cable TV Four beach chairs Gas grill on the back deck Location highlights: 5 minutes to Inkwell Beach and the Steamship Authority Dock Half a mile to the Flying Horses Carousel Close to parks, shops, and plenty of local attractions This stately, antique-filled home offers the true Oak Bluffs experience—comfortable, welcoming, and full of character. If you’re looking for a unique stay that blends history with family-friendly amenities, this is the place.

What this place offers

Outdoor shower
Hair dryer
TV
Microwave
Heating
Desk
Wifi
Baking sheet
Barbecue utensils
Blender

Where you'll sleep

1/2

Bedroom 1

1 king

Bedroom 2

1 queen

Bedroom 3

2 twins

Bedroom 4

2 twins

Oak Bluffs, MA, USA

About the neighborhood

This historic cottage is only five minutes away from Inkwell Beach and the Steamship Authority Dock, and is just a half mile from the Flying Horses Carousel. Circuit Avenue shops and restaurants, arcades, bowling alleys, and ice cream parlors are all nearby.

Getting around

There is 1 off street parking spot. You can walk around Vineyard Haven from here, and a bus is available to explore the rest of the island.

Things to know

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum

Safety & property

Carbon monoxide alarm installed
Fire extinguisher
First aid kit

Cancellation policy

Add your trip dates to get the cancellation details for your stay.

This property is managed through Fairly. It is also available on sites like Airbnb and Vrbo, but the lowest price is always at Fairly.com. Avoid service fees by booking direct.

For homeowners

Company

Connect