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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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 AU$801
includes taxes & fees
2 Nov - 3 Nov
Backyard Retreat / 5 Min > Beach & Main St
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

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 AU$401
includes taxes & fees
10 Nov - 11 Nov
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
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!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"Beautiful and relaxing location."
United States
Lauren F.
The price is AU$652
includes taxes & fees
30 Nov - 1 Dec
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A modern kitchen with white appliances, a teal dining area, and a fireplace.

4. 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 AU$642
includes taxes & fees
3 Nov - 4 Nov
Ellery Bungalow #49 - Minutes from the Sand
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

5. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (36 reviews)
"Ideal property to enjoy all Middletown & Newport have to offer!"
United States
kelly k.
The price is AU$688
includes taxes & fees
2 Nov - 3 Nov
Beach house walking distance to Second Beach
Kitchen island with stools and bright windows

6. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan
Middletown
9.6 out of 10, Exceptional, (18 reviews)
"Best stay "
United States
Justin R.
The price is AU$818
includes taxes & fees
2 Nov - 3 Nov
9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan
A modern kitchen with stainless steel appliances, white cabinets, and a dining area set for four.

7. 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 AU$842
includes taxes & fees
2 Nov - 3 Nov
4br & 2ba Ranch style house w/ huge backyard!
A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

8. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is AU$671
includes taxes & fees
11 Nov - 12 Nov
Vineyard Luxury "Yurt"
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

Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan
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 AU$746
includes taxes & fees
2 Nov - 3 Nov
Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan
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.

10. 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 AU$959
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown
A modern kitchen with a central island, bar stools, stainless steel appliances, and a large window with a view of the outdoors.

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
Delightful 3-bedroom house with AC in Oak Bluffs
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

12. 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, (225 reviews)
"Great location "
United States
Stephanie B.
The price is AU$722
includes taxes & fees
2 Nov - 3 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A sunlit room with a wooden ceiling, large windows, and a stone floor.

13. Third Beach Road

Third Beach Road
Middletown
6.0 out of 10, (1 review)
"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 AU$2,168
includes taxes & fees
8 Nov - 9 Nov
Third Beach Road
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

14. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$1,146
includes taxes & fees
2 Nov - 3 Nov
Walk to Beach! Oak Bluffs Home & Studio
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (11 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A modern kitchen with a stainless steel refrigerator, wooden dining table, and light-colored flooring.

16. 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 AU$1,614
includes taxes & fees
2 Nov - 3 Nov
Spacious Private Cottage Close to Beaches & Newport
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, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A house with a blue door, white porch columns, and two white Adirondack chairs.

18. Spectacular View from Rooftop Deck | Sleeps 12

Spectacular View from Rooftop Deck | Sleeps 12
Easton's Point
8.0 out of 10, Very good, (3 reviews)
"Plenty of room, beautifully appointed. As advertised."
United States
Gerald L.
The price is AU$2,362
includes taxes & fees
2 Nov - 3 Nov
Spectacular View from Rooftop Deck | Sleeps 12
A modern kitchen with stainless steel appliances, a central island with bar stools, and light wood cabinetry.

19. Walk to beach corner lot, 5 bed large yard

Walk to beach corner lot, 5 bed large yard
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place. Clean and well kept"
United States
Michael G.
The price is AU$1,910
includes taxes & fees
2 Nov - 3 Nov
Walk to beach corner lot, 5 bed large yard
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

20. Allston Greens

Allston Greens
Middletown
10.0 out of 10, Exceptional, (14 reviews)
"Nice rental. Good location"
United States
David P.
The price is AU$1,400
includes taxes & fees
22 Nov - 23 Nov
Allston Greens
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

Shore Haven Inn

Shore Haven Inn

8/10 Good
"Relaxed tastefully decorated and furnished property that felt like a home. Laid back breakfast. Beach nearby and 20min walk to local eateries. Only downside was 100% polyester bedsheet, I would expect 100% cotton!"
Andrew 2-night trip
Posted 5 hours ago
Shore Haven Inn

Find out more about Cuttyhunk

Cuttyhunk Holiday Homes information

Number of reviews
143
Accommodation
432 Holiday Homes
Lowest Price
AU$401
Highest Price
AU$2,362

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