COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Search Oak Bluffs Cottages

Search over 1 million properties and 550 airlines worldwide.

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Most hotels are fully refundable. Because flexibility matters.

Browse Select Oak Bluffs Cottages

Cozy Beach Cottage
Oak Bluffs, MA
Located in the heart of Oak Bluffs, this cottage is within a 15-minute walk of Oak Bluffs Public Library and Oak Bluffs Harbor. Inkwell Beach is 0.9 mi (1.4 ...
5/5Exceptional! (5 reviews)
Relaxing stay
"Great location and cottage in oaks bluff. Very well furnished kitchen and really nicely decorated—felt very homey. We really enjoyed our stay. Note: the bedrooms are on the second floor"

Reviewed on Jul 27, 2021

Cozy Beach Cottage
Brand new Carriage House on the Chop
Located in the heart of Oak Bluffs, this romantic cottage is within a 15-minute walk of East Chop Light and Oak Bluffs Harbor. Inkwell Beach is 1.8 mi (2.8 km) ...
5/5Exceptional! (7 reviews)
Beautiful East Chop Carriage House
"Wonderful two bedroom carriage house on a gorgeous East Chop property directly across from East Chop Lighthouse. The carriage house is beautifully appointed, with two spacious bedrooms and a well-equipped gourmet kitchen. Can accommodate two couples or a small family with no problems. The property ..."

Reviewed on Jul 30, 2021

Brand new Carriage House on the Chop
Private Beach Waterfront Oak-bluffs Family Cottage
Nestled on the beach, this Oak Bluffs cottage is within 2 mi (3 km) of Farm Neck Golf Club, Inkwell Beach, and Oak Bluffs Harbor. Seaview Beach and Oak Bluffs ...
5/5Exceptional! (1 review)
Excellent
"Beautiful house and nice view with access to de beach"

Reviewed on Jun 18, 2021

Private Beach Waterfront Oak-bluffs Family Cottage
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
Oak Bluffs 3-Bed Cottage, Walk to Town!
3.5 out of 5
14 Rose Avenue, Oak Bluffs, MA
Situated in Oak Bluffs, this cottage is within a 10-minute walk of Martha's Vineyard Hospital Development and Oak Bluffs Harbor. Inkwell Beach is 1 mi (1.7 km) ...
Oak Bluffs 3-Bed Cottage, Walk to Town!
New! Oak Bluffs Family Home < 1 Mi to Town & Beach
Situated in Oak Bluffs, this cottage is within a 10-minute walk of Oak Bluffs Public Library and Oak Bluffs Harbor. Inkwell Beach is 0.9 mi (1.4 km) away.
New! Oak Bluffs Family Home < 1 Mi to Town & Beach
Don't see what you're looking for?
See all available properties in Oak Bluffs
View all properties
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.

Other property types in Oak Bluffs

MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue, Oak Bluffs, MA
The price is $359 per night from Aug 23 to Aug 23
4.4/5Excellent! (458 reviews)
"Great location."

Reviewed on Jul 31, 2021

MV Surfside Hotel
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is $289 per night from Aug 11 to Aug 11
4.5/5Wonderful! (348 reviews)
"Loved sitting on the porch in a rocker to reflect on our adventures for the day. It is in a great location of everything. Please learn the short cuts to Circuit Street through the cottages. We learned about that on our last day. :) we also did the African American Trail Tour. It was very ..."

Reviewed on Jul 8, 2021

Summercamp
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
4.5/5Wonderful! (261 reviews)
"The hotel is charming. The staff very pleasant and accommodating. There were beach chairs and towels available. The only negative, there were water heater issues, therefore a few cold showers."

Reviewed on Jul 31, 2021

Pequot Hotel
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.

More trip options