A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Cuttyhunk cottages

A wooden deck with Adirondack chairs and a table, surrounded by potted plants and overlooking a body of water.

1. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (16 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is €446
includes taxes & fees
10 Sept - 11 Sept
Charming cottage overlooking the bay in Padanaram Village.
A sandy beach with a bench, a signpost, and a view of the ocean.

2. 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.
The price is €408
includes taxes & fees
7 Sept - 8 Sept
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

3. 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.
WATERFRONT Downtown Cottage w/ Beach
A residential property with a stone staircase leading to a wooden door, surrounded by well-maintained grass and shrubs.

4. 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, (40 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is €573
includes taxes & fees
6 Sept - 7 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
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 Cuttyhunk Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Nice place to stay on the beach."
Rama 1-night trip
Posted 1 hour ago
Vineyard Harbor Motel - Private Beach

Find out more about Cuttyhunk

Cuttyhunk Cottages information

Number of reviews
163
Accommodation
82 Cottages
Lowest Price
€408
Highest Price
€573

Frequently asked questions

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What is there to do in Cuttyhunk near my cottage?
The ideal travel accessory is a well-planned to-do list. Barges Beach is a terrific place to kick off your sightseeing in Cuttyhunk.

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