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 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

Fairhaven

HK$5,704 total

includes taxes & fees

31 Oct - 1 Nov

A living room with a sofa, armchairs, a coffee table with a plant, a side table with a lamp, and a window with curtains.

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

Dartmouth

richard m.

HK$2,549 total

includes taxes & fees

10 Nov - 11 Nov

A patio with outdoor furniture, a tree, and a lattice fence.

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

Fairhaven

Jainessa

HK$4,555 total

includes taxes & fees

31 Oct - 1 Nov

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

4. Ellery Bungalow #49 - Minutes from the Sand

Middletown

Semo A.

HK$3,783 total

includes taxes & fees

3 Nov - 4 Nov

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$4,141 total

includes taxes & fees

27 Oct - 28 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

Jason L.

HK$4,169 total

includes taxes & fees

27 Oct - 28 Oct

7. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

Middletown

Justin R.

HK$4,988 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with stainless steel appliances, white cabinets, and a dining area set for four.

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

PORTSMOUTH

Emo C.

HK$5,105 total

includes taxes & fees

27 Oct - 28 Oct

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

9. Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan

Middletown

Michelle N.

HK$4,710 total

includes taxes & fees

27 Oct - 28 Oct

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

10. Beach house walking distance to Second Beach

Easton's Point

kelly k.

HK$4,418 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Oak Bluffs

Collins E.

HK$8,454 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with a central island, bar stools, stainless steel appliances, and a large window with a view of the outdoors.

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

Oak Bluffs

HK$9,016 total

includes taxes & fees

30 Oct - 31 Oct

A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

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

Oak Bluffs

Chris S.

HK$5,913 total

includes taxes & fees

11 Nov - 12 Nov

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

14. Third Beach Road

Middletown

Janet S.

HK$12,936 total

includes taxes & fees

1 Nov - 2 Nov

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.

15. Stepping Stone

Middletown

George

HK$8,529 total

includes taxes & fees

27 Oct - 28 Oct

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

Falmouth

Stephanie B.

HK$4,102 total

includes taxes & fees

1 Nov - 2 Nov

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

17. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

HK$5,072 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Oak Bluffs

Sherri R.

HK$10,722 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Oak Bluffs

Priyanka D.

HK$17,511 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with a stainless steel refrigerator, wooden dining table, and light-colored flooring.

20. Spacious Private Cottage Close to Beaches & Newport

Middletown

jeffrey w.

HK$9,793 total

includes taxes & fees

1 Nov - 2 Nov

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Top Cuttyhunk Hotel Reviews

New Bedford Harbor Hotel

10/10 Excellent

"Wonderful hotel, I’d love to stay here again."

Best Western Dartmouth-New Bedford

10/10 Excellent

"It was easy to park. Staff were friendly and courteous. The room was clean. The fitness center had a few peices of equipment that are nice if you want to get some cardio or a bit of weight training in. Didnt use the pool but saw a life guaed there during pool swimming hours."

Inn on the Square

8/10 Good

"We enjoyed having a glass of wine by the fire pit in the courtyard area, and the adjoining restaurant for breakfast. Our primary interest was proximity to the Shining Sea Bikeway which was just a block away. Easy stroll to the downtown area with lots of shops and restaurants. We did not use the indoor pool as it was crowded with families which wasn’t our vibe but they were obviously having a great time on a rainy night. Free parking a plus. We would stay here again."

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