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

Holiday Homes in Cuttyhunk

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cuttyhunk holiday homes

A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

1. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is NZ$1,043
includes taxes & fees
30 Sept - 1 Oct
Backyard Retreat / 5 Min > Beach & Main St
A water park with a large central pool, multiple slides, and a variety of play structures.

2. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
The price is NZ$872
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

3. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Dartmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is NZ$572
includes taxes & fees
22 Oct - 23 Oct
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
A wooden deck with a built-in bench and a small enclosed area with a door.

4. 4br & 2ba Ranch style house w/ huge backyard!

4br & 2ba Ranch style house w/ huge backyard!
PORTSMOUTH
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic spot - house was great for visiting with family. Basemen is a great spot for kids to escape. "
United States
Emo C.
The price is NZ$910
includes taxes & fees
27 Sept - 28 Sept
4br & 2ba Ranch style house w/ huge backyard!
A single-story house with a grey siding exterior, a front door with a blue doorbell, and a small front yard with a gravel pathway and various plants.

5. Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (1 review)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is NZ$842
includes taxes & fees
29 Sept - 30 Sept
Ellery Beach Bungalow #45- A Refined Island Escape
A patio area with wicker chairs, a small table, and a house with a shingled exterior.

6. Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
8.6 out of 10, Excellent, (7 reviews)
"Fantastic stay! "
United States
Cristin C.
The price is NZ$842
includes taxes & fees
28 Sept - 29 Sept
Ellery Beach Bungalow #47- Relaxed Island Living
A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

7. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (97 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is NZ$897
includes taxes & fees
22 Oct - 23 Oct
Ellery Bungalow #51- Island Calm Near Newport
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

8. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (35 reviews)
"This is a hidden gem, off the beaten path, yet accessible to all the splendors of this beautiful area. The home is spacious and welcoming. The kitchen offers the opportunity to cook all meals comfortably if wanted. The fire pit is a definite bonus."
United States
Kelley
The price is NZ$1,108
includes taxes & fees
25 Oct - 26 Oct
Beach house walking distance to Second Beach

9. Little Creek Retreat Private hot tub & yard - RIBryan Properties

Little Creek Retreat Private hot tub & yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (18 reviews)
"Best stay "
United States
Justin R.
The price is NZ$2,075
includes taxes & fees
13 Oct - 14 Oct
Little Creek Retreat Private hot tub & yard - RIBryan Properties
A beach with a sandy shore and calm water.

10. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
The price is NZ$1,521
includes taxes & fees
28 Sept - 29 Sept
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

11. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is NZ$1,444
includes taxes & fees
27 Sept - 28 Sept
Oak Bluffs 4BR • 5 Min Drive to Downtown
A spacious living area with a high ceiling, a dining table, and a kitchen area.

12. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is NZ$1,904
includes taxes & fees
4 Oct - 5 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

13. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is NZ$1,605
includes taxes & fees
10 Oct - 11 Oct
Walk to Beach! Oak Bluffs Home & Studio
A modern kitchen with white appliances, a teal dining area, and a fireplace.

14. Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Very close to the beach. Would highly recommend"
United States
Semo A.
The price is NZ$842
includes taxes & fees
28 Sept - 29 Sept
Ellery Bungalow #49 - Minutes from the Sand
A two-story house with a stone chimney, a red front door, and a porch with white railings.

15. Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay at this lovely home. The hot tub was very fun and huge kitchen table was nice for our family. It was conveniently located and well cleaned before our arrival. We recommend this fun spot in Newport."
United States
Michelle N.
The price is NZ$1,550
includes taxes & fees
26 Oct - 27 Oct
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

16. 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, (223 reviews)
"Great location "
United States
Stephanie B.
The price is NZ$1,005
includes taxes & fees
18 Oct - 19 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

17. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is NZ$2,306
includes taxes & fees
10 Oct - 11 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A room with a sliding glass door leading to a patio with a table and chairs, a sofa, and a small table with a vase of flowers.

18. Stepping Stone

Stepping Stone
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"This vacation place was clean, beautiful and comfortable with easy access to downturn Newport, the beaches and all the area has to offer. Perfect stay for our family wedding weekend."
United States
George
Stepping Stone
A modern kitchen with a stainless steel refrigerator, wooden dining table, and light-colored flooring.

19. Spacious Private Cottage Close to Beaches & Newport

Spacious Private Cottage Close to Beaches & Newport
Middletown
9.6 out of 10, Exceptional, (4 reviews)
"One of the best VRBO properties we’ve ever stayed at!"
United States
jeffrey w.
The price is NZ$2,591
includes taxes & fees
15 Oct - 16 Oct
Spacious Private Cottage Close to Beaches & Newport
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

20. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is NZ$3,801
includes taxes & fees
10 Oct - 11 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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

Town & Beach Motel

Town & Beach Motel

10/10 Excellent
"Very nice clean room. I enjoyed it very much"
eddie 1-night trip
Posted 5 hours ago
Town & Beach Motel

Find out more about Cuttyhunk

Cuttyhunk Holiday Homes information

Number of reviews
483
Accommodation
432 Holiday Homes
Lowest Price
NZ$572
Highest Price
NZ$3,801

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