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

Search Cuttyhunk Cottage Rentals from CA $650

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Check prices for these dates

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

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 CA $434
CA $719 total
includes taxes & fees
Sep 10 - Sep 11
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 CA $346
CA $650 total
includes taxes & fees
Sep 6 - Sep 7
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.
The price is CA $954
CA $1,483 total
includes taxes & fees
Sep 8 - Sep 9
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, (41 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is CA $716
CA $914 total
includes taxes & fees
Sep 9 - Sep 10
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

Harbor Landing Resort

Harbor Landing Resort

8/10 Good
"Great location, lots of parking lots of shelf, space and jars, large common areas."
KIMBERLY 3-night trip
Posted 5 hours ago
Harbor Landing Resort

Find out more about Cuttyhunk

Cuttyhunk Cottages information

Number of reviews
164
Accommodation
82 Cottages
Lowest Price
CA $650
Highest Price
CA $1,483

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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