A row of colorful, historic houses with a central path.

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Oak Bluffs cottages

Property grounds

1. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is AED 918
AED 1,875 total
includes taxes & fees
2 Sep - 3 Sep
Make Lasting Memories In This Adorable Vineyard Cottage!
Property grounds

2. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (39 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is AED 3,118
AED 3,971 total
includes taxes & fees
6 Sep - 7 Sep
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Terrace/patio

3. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (53 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is AED 3,306
AED 4,862 total
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT Downtown Cottage w/ Beach
Outdoor dining

4. Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
Chappy cottage with private beach
Exterior

5. Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Barnstable
8.6 out of 10, Excellent, (30 reviews)
"It was very comfortable with upgraded kitchen and bathroom. It had all we needed. The owner was very responsive . Easy check in process. The location was perfect, just across from a beautiful ocean beach and very near Hyannis and many attractions. "
United States
Helene M.
The price is AED 975
AED 1,974 total
includes taxes & fees
19 Aug - 20 Aug
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
House (3 Bedrooms) | Interior

6. Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
3.0 star property
Centerville
The price is AED 911
AED 2,328 total
includes taxes & fees
19 Aug - 20 Aug
Bike to Beach: Centerville Home w/ Deck!
Beach nearby, sun loungers, beach umbrellas, beach towels

7. 3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Mattapoisett
9.6 out of 10, Exceptional, (52 reviews)
"The area was beautiful! We went mid August and the neighborhood had gorgeous flowers blooming everywhere. The beach area was private and so relaxing. Our pup loved exploring the doggy beach. Good area for restaurants too… we really enjoyed Turk’s!"
United States
Helen R.
The price is AED 918
AED 1,731 total
includes taxes & fees
6 Sep - 7 Sep
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
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

Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Perfect location, great ambiance, beautiful sunsets! Great restaurant on property including the best ice cream store must try Oreo cookie flavor. Loved it!"
Sheerlee 4-night trip
Posted 7 hours ago
Sea Crest Beach Resort

Frequently asked questions

How much do cottages in Oak Bluffs cost?
Cottages in Oak Bluffs range between AED 1,731 and AED 5,777 per night. These stays offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Oak Bluffs?
Enjoy reconnecting with nature in one of the 238 cottages available in Oak Bluffs. To help you choose a property that's right for you, take advantage of our filters to search for perks or amenities you need.
Why book your cottage in Oak Bluffs with Expedia?
We think that traveling should be easy, so if you're after cottages in Oak Bluffs at a nice price, Expedia delivers. Stick to the budget and pick a thrifty option far from the rush of the city, or book an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Oak Bluffs?
Expedia is here to help you track down cheap cottages in Oak Bluffs. To book your special stay in a couple of clicks, simply use the filter tool to refine your search by star rating, budget and amenities.