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. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is AED 634
AED 2,070 total
includes taxes & fees
30 Sep - 1 Oct
Backyard Retreat / 5 Min > Beach & Main St

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 826
AED 1,731 total
includes taxes & fees
30 Sep - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

3. 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 481
AED 1,132 total
includes taxes & fees
22 Oct - 23 Oct
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

4. 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 735
AED 1,809 total
includes taxes & fees
27 Sep - 28 Sep
4br & 2ba Ranch style house w/ huge backyard!

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

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (1 review)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is AED 492
AED 1,671 total
includes taxes & fees
28 Sep - 29 Sep
Ellery Beach Bungalow #45- A Refined Island Escape

6. 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 AED 492
AED 1,671 total
includes taxes & fees
29 Sep - 30 Sep
Ellery Beach Bungalow #47- Relaxed Island Living

7. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (97 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is AED 577
AED 1,777 total
includes taxes & fees
22 Oct - 23 Oct
Ellery Bungalow #51- Island Calm Near Newport

8. 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)
"This is a hidden gem, off the beaten path, yet accessible to all the splendors of this beautiful area. The home is spacious and welcoming. The kitchen offers the opportunity to cook all meals comfortably if wanted. The fire pit is a definite bonus."
United States
Kelley
The price is AED 658
AED 2,249 total
includes taxes & fees
25 Oct - 26 Oct
Beach house walking distance to Second Beach

9. 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 1,915
AED 3,360 total
includes taxes & fees
26 Oct - 27 Oct
Little Creek Retreat Private hot tub & yard - RIBryan Properties

10. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
The price is AED 1,451
AED 3,077 total
includes taxes & fees
28 Sep - 29 Sep
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

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 1,319
AED 2,917 total
includes taxes & fees
27 Sep - 28 Sep
Oak Bluffs 4BR • 5 Min Drive to Downtown

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, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is AED 1,818
AED 3,701 total
includes taxes & fees
4 Oct - 5 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

13. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AED 1,429
AED 3,311 total
includes taxes & fees
9 Oct - 10 Oct
Walk to Beach! Oak Bluffs Home & Studio

14. 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

15. 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 1,762
AED 3,094 total
includes taxes & fees
26 Oct - 27 Oct
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

16. 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 845
AED 2,043 total
includes taxes & fees
18 Oct - 19 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is AED 1,462
AED 4,735 total
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

18. 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

19. 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.
Spacious Private Cottage Close to Beaches & Newport

20. 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 7,746 total
includes taxes & fees
27 Sep - 28 Sep
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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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