Search Oak Bluffs Cottage Rentals from CA $344

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Oak Bluffs Cottages

Cozy Beach Cottage
Stroll along the beach and enjoy the calm waters from the end of the pier.

Cozy Beach Cottage

10.0 out of 10, Exceptional, (48)
"The property was prepared, very thoughtful and had everything you could think of for a wonderful beach Island stay. The only downside was cable because I’m addicted to TV and I would’ve appreciated at least a smart TV that I could connect my own Netflix. "
Cozy Beach Cottage
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Enjoy cooking in this well-equipped kitchen with a stove, microwave, and sink.

Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach

9.6 out of 10, Exceptional, (5)
"The Pinkletink was a quaint home for a wonderful visit to Martha's Vinyard. It is in a quiet neighborhood and a nice walk from both the beach and the town of Oak Bluffs. Perfect location for a couple wanting to visit Martha's Vinyard and enjoy the island."
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Make Lasting Memories In This Adorable Vineyard Cottage!
Set amidst lush greenery, this charming chapel offers a serene atmosphere.

Make Lasting Memories In This Adorable Vineyard Cottage!

9.8 out of 10, Exceptional, (146)
"Absolutely loved this place. Had everything we needed. Such cute decor. Perfect cute little rental in convenient location. "
The price is CA $344
CA $701 total
includes taxes & fees
Sep 1 - Sep 2
Make Lasting Memories In This Adorable Vineyard Cottage!
Cozy Family Cottage Circuit Ave OB Walk to Everything
Enjoy the view from this cozy porch with a wicker chair and a glimpse of the surrounding neighborhood.

Cozy Family Cottage Circuit Ave OB Walk to Everything

2.0 star property
Cozy Family Cottage Circuit Ave OB Walk to Everything
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Relax and unwind in this serene outdoor space, featuring a TV for entertainment, a dining table, and comfortable seating.

Charming MV Cottage: Walk to Dtwn Oak Bluffs!

3.0 star property
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Relax in an outdoor space with a hot tub and patio.

Cozy vineyard cottage close to downtown with outdoor living space and amentiies.

8.0 out of 10, Very good, (1)
"The property manager was wonderful to work with. The property location was perfect. The property was fairly clean but did have a musty smell. Would suggest the use of a dehumidifier. Overall, our stay here was great and enjoyable. We would definitely stay here again."
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Beautiful Carriage House on the Chop
Two-story house with a stone wall and mature trees surrounding the property.

Beautiful Carriage House on the Chop

10.0 out of 10, Exceptional, (24)
"Loved staying at The Carriage House! Very beautiful place to relax and plan all the wonderful things you get to do on the island. Easy communication, very comfortable beds and well stocked kitchen."
Beautiful Carriage House on the Chop
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
Enter a stylish space with a plush sofa, wicker stool, and patterned rug.

OB Cozy-Cottage-Glam off Circuit with Great Outdoor living

9.2 out of 10, Wonderful, (7)
"Great location for quick access to all Oak Bluffs hotspots. Great porch and outdoor space. Owner was extremely responsive and helpful."
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
Spacious Home - 1500 ft from Beach & Circuit Ave
Relax in this inviting living room with a leather sofa, armchair, and coffee table.

Spacious Home - 1500 ft from Beach & Circuit Ave

10.0 out of 10, Exceptional, (12)
"Great stay, clean, great location and Judy the owner was always available if anything came up!"
Spacious Home - 1500 ft from Beach & Circuit Ave
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Relax on the covered deck with a TV, table, and bench.

Charming MV Cottage: Walk to Dtwn Oak Bluffs!

9.6 out of 10, Exceptional, (4)
"The location is very convenient. The family enjoyed the fun in the sun."
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Oak Bluffs 3-Bed Cottage, Walk to Town
Compact kitchen with oven, stainless steel range hood, microwave, and modern sink.

Oak Bluffs 3-Bed Cottage, Walk to Town

3.5 star property
Oak Bluffs 3-Bed Cottage, Walk to Town
Steps to Inkwell Beach: Victorian Home!
House (6 Bedrooms) | Interior

Steps to Inkwell Beach: Victorian Home!

3.0 star property
Steps to Inkwell Beach: Victorian Home!
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
House (2 Bedrooms) | Interior

Martha's Vineyard Home: Walk to Oak Bluffs Beach!

3.0 star property
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Traditional Martha's Vineyard Home w/ Porch & Yard
Relax on the covered porch with a view of the outdoors, featuring two comfortable chairs and large windows.

Traditional Martha's Vineyard Home w/ Porch & Yard

3.0 star property
Traditional Martha's Vineyard Home w/ Porch & Yard
Vineyard Gem < 2 Mi to Beach & Oak Bluffs!
Microwave, oven, stovetop, dishwasher

Vineyard Gem < 2 Mi to Beach & Oak Bluffs!

3.0 star property
Vineyard Gem < 2 Mi to Beach & Oak Bluffs!
Vineyard charm island memories
Enjoy dining on the porch with a gabled roof and balcony overlooking the surroundings.

Vineyard charm island memories

Vineyard charm island memories
GingerBread Cottage at Oak Bluffs
Enjoy a serene beach experience with access to turquoise waters and a sandy shore.

GingerBread Cottage at Oak Bluffs

GingerBread Cottage at Oak Bluffs
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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Top Oak Bluffs Hotel Reviews

The Attleboro House

The Attleboro House

10/10 Excellent
"We will be staying here again in the future!"
Matthew 2-night trip
Posted 2 days ago
The Attleboro House