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

Cuttyhunk Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Cuttyhunk vacation 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 CA $267
CA $878 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $406
CA $820 total
includes taxes & fees
Oct 31 - Nov 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A wooden deck with a built-in bench and a small enclosed area with a door.

3. 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 CA $392
CA $879 total
includes taxes & fees
Oct 12 - Oct 13
4br & 2ba Ranch style house w/ huge backyard!
A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

4. Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Furnished & Flexible – Perfect for Longer Stays 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 CA $168
CA $441 total
includes taxes & fees
Oct 22 - Oct 23
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
A bedroom with a white bed, two nightstands with lamps, a window with curtains, and a ceiling vent.

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

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is CA $191
CA $683 total
includes taxes & fees
Oct 12 - Oct 13
Ellery Beach Bungalow #45- A Refined Island Escape
A backyard with a seating area, a white fence, and a variety of plants.

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is CA $639
CA $1,639 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs
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, (98 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is CA $191
CA $683 total
includes taxes & fees
Oct 12 - Oct 13
Ellery Bungalow #51- Island Calm Near Newport
A sunlit room with a wooden ceiling, large windows, and a stone floor.

8. 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 CA $992
CA $2,475 total
includes taxes & fees
Oct 18 - Oct 19
Third Beach Road
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.

9. 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
The price is CA $530
CA $1,419 total
includes taxes & fees
Oct 12 - Oct 13
Stepping Stone
A patio area with wicker chairs, a small table, and a house with a shingled exterior.

10. 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 CA $191
CA $683 total
includes taxes & fees
Oct 12 - Oct 13
Ellery Beach Bungalow #47- Relaxed Island Living
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

11. 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)
"Great place and very welcoming host. Nearby to second beach in a quiet neighborhood."
United States
Melissa G.
The price is CA $255
CA $925 total
includes taxes & fees
Oct 25 - Oct 26
Beach house walking distance to Second Beach
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, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is CA $706
CA $1,537 total
includes taxes & fees
Oct 12 - Oct 13
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

13. 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.
The price is CA $567
CA $1,908 total
includes taxes & fees
Oct 12 - Oct 13
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

14. 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 CA $426
CA $1,089 total
includes taxes & fees
Nov 11 - Nov 12
Oak Bluffs 4BR • 5 Min Drive to Downtown
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

15. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $555
CA $1,319 total
includes taxes & fees
Oct 12 - Oct 13
Walk to Beach! Oak Bluffs Home & Studio
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

16. Allston Greens

Allston Greens
Middletown
10.0 out of 10, Exceptional, (14 reviews)
"Nice rental. Good location"
United States
David P.
The price is CA $616
CA $1,531 total
includes taxes & fees
Oct 30 - Oct 31
Allston Greens
A modern kitchen with a stainless steel refrigerator, wooden dining table, and light-colored flooring.

17. 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 CA $753
CA $1,865 total
includes taxes & fees
Oct 12 - Oct 13
Spacious Private Cottage Close to Beaches & Newport
A spacious living room with a dark blue sectional sofa, a white coffee table, and a patterned armchair.

18. Solo Fish - Family home, walk to beach and pool!

Solo Fish - Family home, walk to beach and pool!
Middletown
9.4 out of 10, Exceptional, (3 reviews)
"Good space. Fun backyard area."
United States
Rosie G.
The price is CA $971
CA $2,121 total
includes taxes & fees
Oct 12 - Oct 13
Solo Fish - Family home, walk to beach and pool!
An aerial view of a coastal residential area with houses, a beach, and a body of water.

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, (1 review)
The price is CA $731
CA $1,929 total
includes taxes & fees
Nov 5 - Nov 6
Walk to beach corner lot, 5 bed large yard
A modern kitchen with white appliances, a teal dining area, and a fireplace.

20. 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 CA $191
CA $683 total
includes taxes & fees
Oct 12 - Oct 13
Ellery Bungalow #49 - Minutes from the Sand
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

Inn on the Square

Inn on the Square

10/10 Excellent
"Very comfortable bed!"
Tyler 1-night trip
Posted 18 hours ago
Inn on the Square

Find out more about Cuttyhunk

Cuttyhunk Vacation Homes information

Number of reviews
228
Accommodation
440 Vacation Homes
Lowest Price
CA $441
Highest Price
CA $2,475

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