Cuttyhunk Vacation Homes

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

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Our top choices for Cuttyhunk holiday homes

A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

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

Dartmouth

richard m.

HK$2,401 total

includes taxes & fees

22 Oct - 23 Oct

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

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

Fairhaven

HK$4,865 total

includes taxes & fees

13 Oct - 14 Oct

A water park with a large central pool, multiple slides, and a variety of play structures.

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

Fairhaven

Jainessa

HK$4,532 total

includes taxes & fees

31 Oct - 1 Nov

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.

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

Middletown

Dana N.

HK$3,731 total

includes taxes & fees

13 Oct - 14 Oct

A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

5. Ellery Bungalow #51- Island Calm Near Newport

Middletown

Stacey

HK$3,731 total

includes taxes & fees

13 Oct - 14 Oct

A patio area with wicker chairs, a small table, and a house with a shingled exterior.

6. Ellery Beach Bungalow #47- Relaxed Island Living

Middletown

Cristin C.

HK$3,731 total

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

7. Beach house walking distance to Second Beach

Easton's Point

Melissa G.

HK$5,091 total

includes taxes & fees

25 Oct - 26 Oct

A wooden deck with a built-in bench and a small enclosed area with a door.

8. 4br & 2ba Ranch style house w/ huge backyard!

PORTSMOUTH

Emo C.

HK$4,822 total

includes taxes & fees

13 Oct - 14 Oct

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

Middletown

Justin R.

HK$4,991 total

includes taxes & fees

14 Oct - 15 Oct

A backyard with a seating area, a white fence, and a variety of plants.

10. Delightful 3-bedroom house with AC in Oak Bluffs

Oak Bluffs

HK$8,987 total

includes taxes & fees

30 Oct - 31 Oct

A two-story house with a stone chimney, a red front door, and a porch with white railings.

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

Middletown

Michelle N.

HK$5,837 total

includes taxes & fees

13 Oct - 14 Oct

A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

Oak Bluffs

Karen M.

HK$8,459 total

includes taxes & fees

14 Oct - 15 Oct

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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

Oak Bluffs

Chris S.

HK$6,005 total

includes taxes & fees

11 Nov - 12 Nov

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

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

Falmouth

Stephanie B.

HK$4,087 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white appliances, a teal dining area, and a fireplace.

15. Ellery Bungalow #49 - Minutes from the Sand

Middletown

Semo A.

HK$3,731 total

includes taxes & fees

13 Oct - 14 Oct

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.

16. Stepping Stone

Middletown

George

HK$7,813 total

includes taxes & fees

13 Oct - 14 Oct

A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

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

Oak Bluffs

Priyanka D.

HK$16,804 total

includes taxes & fees

13 Oct - 14 Oct

A sunlit room with a wooden ceiling, large windows, and a stone floor.

18. Third Beach Road

Middletown

Janet S.

HK$13,623 total

includes taxes & fees

18 Oct - 19 Oct

A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

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

Oak Bluffs

Sherri R.

HK$10,729 total

includes taxes & fees

13 Oct - 14 Oct

A circular stone patio with Adirondack chairs and a small table in a forested area.

20. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

HK$5,610 total

includes taxes & fees

13 Oct - 14 Oct

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Top Cuttyhunk Hotel Reviews

New Bedford Harbor Hotel

8/10 Good

"ALL HOTELS EVERYWHERE should always have GOOD coffee on....ALWAYS....."

Whaler Inn and Suites

10/10 Excellent

"The staff were exceptional. Extremely friendly and helpful throughout my stay. Special shout out to receptionist April who was beyond superb. The continental breakfast was just what I needed. The rooms were spacious, very clean and came with a microwave fridge and coffee maker, and all worked perfectly. The bed was quite large and very comfortable. The parking lot is very safe. They have lights outside and security cameras. I felt very safe, leaving my car there and having contents within it. There are also a lot of nice restaurants nearby, but you won’t always need them because Ryan’s restaurant and pub inside the hotel is exceptional. Again, very kind and helpful waiting staff and the food is high quality. The hotel is also located not too far from the highway, making travel very convenient. It’s also close to downtown New Bedford so there’s much to do in the surrounding areas. I highly recommend this hotel and think it was just exceptional."

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