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

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Oak Bluffs cottages

A residential property with a stone staircase leading to a wooden door, surrounded by well-maintained grass and shrubs.

1. 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, (41 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is AU$930
includes taxes & fees
9 Sept - 10 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

2. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (54 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is AU$1,434
includes taxes & fees
8 Sept - 9 Sept
WATERFRONT Downtown Cottage w/ Beach
A wooden deck with wicker furniture, including two sofas and a chair, and a large umbrella.

3. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
A wooden deck with wicker furniture, including two sofas and a chair, and a large umbrella.

4. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
The price is AU$860
includes taxes & fees
5 Oct - 6 Oct
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
A wooden deck with a table and chairs, a red umbrella, and a view of the water.

5. Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (19 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
A house surrounded by dense forest, overlooking a body of water.

6. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
A sandy beach with a bench, a signpost, and a view of the ocean.

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, (53 reviews)
"We had a great stay! The community the home is located in was so quiet. The place was so clean, you would not know it was pet friendly! Our hosts had everything we needed and then some, from extra dog supplies to books to keep our toddler occupied. And our hosts kept the check in, stay and check out instructions simple. We would definitely book this place again!"
United States
Shawn A.
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
A wooden deck with a table and chairs, overlooking a forested area.

8. Mashpee Heaven Lake front

Mashpee Heaven Lake front
Mashpee
8.0 out of 10, Very good, (1 review)
"Location was very nice. The kayaks were a plus. The interior was like retro 1960's, but very comfortable. The exterior was a bit unkempt."
United States
Richard B.
The price is AU$1,288
includes taxes & fees
14 Sept - 15 Sept
Mashpee Heaven Lake front
A single-story house with a front door, a small porch, and a gravel driveway.

9. 1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
9.0 out of 10, Wonderful, (22 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
The price is AU$501
includes taxes & fees
2 Oct - 3 Oct
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
A single-story house with a front door, a small porch, and a gravel driveway.

10. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
The price is AU$505
includes taxes & fees
2 Oct - 3 Oct
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
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

Summercamp

Summercamp

10/10 Excellent
"The complimentary bicycle and the beach towels were a nice bonus."
franklin 3-night trip
Posted 14 hours ago
Summercamp

Find out more about Oak Bluffs

Oak Bluffs Cottages information

Number of reviews
1
Accommodation
228 Cottages
Lowest Price
AU$505
Highest Price
AU$861

Frequently asked questions

How much do cottages in Oak Bluffs cost?
Cottages in Oak Bluffs range between AU$505 and AU$861 per night. These stays offer a chance to get in touch with nature — at a price you can afford. This price was 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 the beauty of nature in one of the 228 cottages located in Oak Bluffs. To help you choose your ideal place, click on our handy filters to search for perks or amenities you prefer.
What is there to do in Oak Bluffs near my cottage?
Oak Bluffs has enough experiences and activities to keep you amused for weeks (or months!), beginning with Inkwell Beach. Oak Bluffs Town Beach, Falmouth Heights Beach and Marthas Vineyard Museum are other wonderful attractions. If you're lingering longer, Lighthouse Beach and Surf Drive Beach will add the finishing touches to your itinerary.