Holiday Homes in Cuttyhunk

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Cuttyhunk holiday homes

Exterior detail
Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (1)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is NZ$742
includes taxes & fees
20 Jan - 21 Jan 2026
Ellery Beach Bungalow #45- A Refined Island Escape
TV
Blue Haven Houseboat

Blue Haven Houseboat

Blue Haven Houseboat
2.0 star property
New Bedford
The price is NZ$237
includes taxes & fees
6 Jan - 7 Jan 2026
Blue Haven Houseboat
Property grounds
Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
10.0 out of 10, Exceptional, (4)
"Fantastic stay! "
United States
Cristin C.
The price is NZ$746
includes taxes & fees
20 Jan - 21 Jan 2026
Ellery Beach Bungalow #47- Relaxed Island Living
TV
Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (94)
"My family had an amazing stay at this bungalow. It is very clean and offered everything we needed for our stay in Newport. The beach is very close and there are plenty of restaurants and convenience store within walking distance. "
United States
Tamara C.
The price is NZ$762
includes taxes & fees
20 Jan - 21 Jan 2026
Ellery Bungalow #51- Island Calm Near Newport
Interior
Beach house walking distance to Second Beach

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (26)
"What a great location, well appointed home, and a very professional VRBO host. You know that love and care goes into making guests feel welcomed and special. Lots of amenities and space to make your stay memorable. "
United States
Victoria L.
The price is NZ$947
includes taxes & fees
1 Jan - 2 Jan 2026
Beach house walking distance to Second Beach
TV
Between Beaches

Between Beaches

Between Beaches
Easton's Point
8.0 out of 10, Very good, (1)
The price is NZ$1,144
includes taxes & fees
4 Jan - 5 Jan 2026
Between Beaches
Interior
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is NZ$846
includes taxes & fees
4 Jan - 5 Jan 2026
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Dining
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Dartmouth
The price is NZ$524
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Exterior
The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft
Mattapoisett
9.8 out of 10, Exceptional, (8)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
United States
Catherine T.
The price is NZ$3,092
includes taxes & fees
7 Jan - 8 Jan 2026
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is NZ$2,074
includes taxes & fees
26 Dec - 27 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Exterior detail
Stones Throw Waterfront

Stones Throw Waterfront

Stones Throw Waterfront
Dartmouth
8.8 out of 10, Excellent, (6)
"Perfect spot for our long weekend visiting local family and we wish we could have stayed longer. Close to the village, kayaks on site/ water view- house clean and decorated thoughtfully. Pet friendly, we brought our small dog. The outdoor shower is a must try! We hope to be back soon! "
United States
Lauren G.
The price is NZ$1,091
includes taxes & fees
26 Dec - 27 Dec
Stones Throw Waterfront
Fridge, microwave, oven, stovetop
Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (14)
"Great place! So many bedrooms! Nice private yard, great if you have a dog. Had a wonderful stay, would stay again. Close enough to Newport to drive in and out no problem, plus close to beaches. "
United States
Todd C.
The price is NZ$1,142
includes taxes & fees
29 Dec - 30 Dec
Little Creek Retreat - RIBryan Property
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (3)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is NZ$1,529
includes taxes & fees
26 Dec - 27 Dec
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Fridge, microwave, oven, stovetop
Allston Greens

Allston Greens

Allston Greens
Middletown
10.0 out of 10, Exceptional, (9)
"Great location and perfect layout of the home for our needs"
United States
Anna P.
The price is NZ$1,645
includes taxes & fees
6 Jan - 7 Jan 2026
Allston Greens
Exterior
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is NZ$1,856
includes taxes & fees
30 Dec - 31 Dec
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Exterior
Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (13)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
The price is NZ$1,181
includes taxes & fees
22 Jan - 23 Jan 2026
Middletown Bungalow - RIBryan Property
Exterior
Double lot walk to beach 5 bed 7 bath, large yard

Double lot walk to beach 5 bed 7 bath, large yard

Double lot walk to beach 5 bed 7 bath, large yard
Easton's Point
9.8 out of 10, Exceptional, (26)
"We enjoyed our stay at the home. Very well maintained."
United States
Anmol P.
The price is NZ$2,634
includes taxes & fees
5 Jan - 6 Jan 2026
Double lot walk to beach 5 bed 7 bath, large yard
Smart TV, books
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Dartmouth
10.0 out of 10, Exceptional, (14)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
The price is NZ$2,472
includes taxes & fees
27 Dec - 28 Dec
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Beach nearby
Walk to beach corner lot, 5 bed large yard

Walk to beach corner lot, 5 bed large yard

Walk to beach corner lot, 5 bed large yard
Middletown
The price is NZ$4,904
includes taxes & fees
6 Jan - 7 Jan 2026
Walk to beach corner lot, 5 bed large yard
Interior
Third Beach Road

Third Beach Road

Third Beach Road
2.0 star property
Middletown
6.0 out of 10, (1)
"Renovated house, very cute. Kitchen was definitely a highlight as it was a good space for cooking and gathering together. Some amenities of house were not exactly as listed in description. Location of house was nice-close to beach and park with pickleball courts, easy access to Newport wharves and restaurants "
United States
Janet S.
The price is NZ$2,577
includes taxes & fees
6 Jan - 7 Jan 2026
Third Beach Road
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

Residence Inn by Marriott New Bedford Dartmouth

Residence Inn by Marriott New Bedford Dartmouth

10/10 Excellent
"Everyone was awesome. Especially the young man working the desk as well as housekeeping. We spent the weekend for my daughter’s bday and she had so much fun. Breakfast was not the greatest. We got there at 745 and it was all cold and hard but everything else was awesome. Thank you for having us. Merry Christmas "
Amanda 2-night trip
Posted 3 days ago
Residence Inn by Marriott New Bedford Dartmouth

Find out more about Cuttyhunk

Cuttyhunk Holiday Homes information

Number of reviews
393
Accommodation
468 Holiday Homes
Lowest Price
NZ$237
Highest Price
NZ$4,904

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