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, (1 review)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is AED 481
AED 1,186 total
includes taxes & fees
25 Sep - 26 Sep
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 826
AED 1,854 total
includes taxes & fees
30 Sep - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

3. 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 1,759 total
includes taxes & fees
10 Sep - 11 Sep
Ellery Beach Bungalow #45- A Refined Island Escape

4. 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 639
AED 1,961 total
includes taxes & fees
13 Sep - 14 Sep
Ellery Bungalow #51- Island Calm Near Newport

5. 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 632
AED 1,948 total
includes taxes & fees
13 Sep - 14 Sep
Ellery Beach Bungalow #47- Relaxed Island Living

6. 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 1,157
AED 3,118 total
includes taxes & fees
11 Sep - 12 Sep
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

7. 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 823
AED 2,504 total
includes taxes & fees
13 Sep - 14 Sep
Beach house walking distance to Second Beach

8. Little Creek Retreat Private hot tub & yard - RIBryan Properties

Little Creek Retreat Private hot tub & yard - RIBryan Properties
Middletown
9.4 out of 10, Exceptional, (16 reviews)
"Best stay "
United States
Justin R.
The price is AED 1,192
AED 2,754 total
includes taxes & fees
14 Sep - 15 Sep
Little Creek Retreat Private hot tub & yard - RIBryan Properties

9. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AED 1,429
AED 3,430 total
includes taxes & fees
13 Sep - 14 Sep
Walk to Beach! Oak Bluffs Home & Studio

10. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AED 1,466
AED 3,044 total
includes taxes & fees
27 Sep - 28 Sep
Charming Vacation Home in Oak Bluffs.

11. 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, (18 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.
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

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, (221 reviews)
"Great location "
United States
Stephanie B.
The price is AED 1,010
AED 2,379 total
includes taxes & fees
5 Oct - 6 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

13. 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

14. 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, (8 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
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

15. Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow
Falmouth
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

16. 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

17. Spacious Private Cottage Close to Beaches & Newport

Spacious Private Cottage Close to Beaches & Newport
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"This property was great for our combined family vacation. Situated on a quiet side street safe enough for our children to ride bikes and an after dinner family bike ride. The property provided ample adult sized bikes, beach chairs, beach toys and even 2 large wagons - close enough to walk or ride a bike to Easton’s beach. Would definitely book again."
United States
Ryan R.
Spacious Private Cottage Close to Beaches & Newport

18. 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 7,865 total
includes taxes & fees
10 Sep - 11 Sep
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

19. 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.
Third Beach Road

20. 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)
Walk to beach corner lot, 5 bed large yard
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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