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 vacation homes

1. 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 AED 433
AED 1,136 total
includes taxes & fees
22 Oct - 23 Oct
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

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 AED 1,047
AED 2,133 total
includes taxes & fees
31 Oct - 1 Nov
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

3. 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
Ellery Bungalow #51- Island Calm Near Newport

4. 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.
Ellery Beach Bungalow #47- Relaxed Island Living

5. 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.
Ellery Bungalow #49 - Minutes from the Sand

6. 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 AED 658
AED 2,383 total
includes taxes & fees
25 Oct - 26 Oct
Beach house walking distance to Second Beach

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 AED 1,010
AED 2,274 total
includes taxes & fees
18 Oct - 19 Oct
4br & 2ba Ranch style house w/ huge backyard!

8. 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 AED 932
AED 2,340 total
includes taxes & fees
21 Oct - 22 Oct
Little Creek Retreat Private hot tub & yard - RIBryan Properties

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is AED 1,646
AED 4,206 total
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs

10. 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)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is AED 1,818
AED 3,959 total
includes taxes & fees
17 Oct - 18 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 AED 1,098
AED 2,737 total
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

12. 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 AED 1,321
AED 2,736 total
includes taxes & fees
9 Nov - 10 Nov
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

13. 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, (224 reviews)
"Great location "
United States
Stephanie B.
The price is AED 661
AED 1,913 total
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

14. 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

15. 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 AED 4,959
AED 8,123 total
includes taxes & fees
17 Oct - 18 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

16. 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 AED 2,556
AED 6,376 total
includes taxes & fees
18 Oct - 19 Oct
Third Beach Road

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

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is AED 1,161
AED 2,626 total
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

18. Beach! Beach! Beach! Walk to Easton's Beach!

Beach! Beach! Beach! Walk to Easton's Beach!
Middletown
9.8 out of 10, Exceptional, (42 reviews)
"a very nice, clean and comfortable home. perfect for families and couples staying near Newport RI. Host is amazing and we highly recommend this place."
United States
marc p.
Beach! Beach! Beach! Walk to Easton's Beach!

19. 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 AED 1,462
AED 5,022 total
includes taxes & fees
17 Oct - 18 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

20. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is AED 9,183
AED 14,056 total
includes taxes & fees
18 Oct - 19 Oct
Beautiful Estate with salt water pool & pond with kayaks
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

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