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

Holiday Homes in Cuttyhunk

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Our top choices for Cuttyhunk holiday homes

1. 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, (1 review)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
Cozy Autumn Escape Near Fall Foliage 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 AU$689
includes taxes & fees
30 Sept - 1 Oct
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, (97 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is AU$675
includes taxes & fees
20 Sept - 21 Sept
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.
The price is AU$725
includes taxes & fees
24 Sept - 25 Sept
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.
The price is AU$660
includes taxes & fees
22 Sept - 23 Sept
Ellery Bungalow #49 - Minutes from the Sand

6. Pop, Bubble, and sun-drenched Cutie Cottage!

Pop, Bubble, and sun-drenched Cutie Cottage!
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We loved our stay! The cottage was the perfect size for what we needed and a great location! We would definitely stay again."
United States
Lauren C.
The price is AU$742
includes taxes & fees
26 Sept - 27 Sept
Pop, Bubble, and sun-drenched Cutie Cottage!

7. 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 AU$1,158
includes taxes & fees
17 Sept - 18 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 AU$896
includes taxes & fees
24 Sept - 25 Sept
Beach house walking distance to Second Beach

9. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AU$1,123
includes taxes & fees
4 Oct - 5 Oct
Charming Vacation Home in Oak Bluffs.

10. 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
The price is AU$1,413
includes taxes & fees
20 Sept - 21 Sept
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

11. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$1,317
includes taxes & fees
1 Oct - 2 Oct
Walk to Beach! Oak Bluffs Home & Studio

12. 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 AU$979
includes taxes & fees
21 Sept - 22 Sept
Little Creek Retreat Private hot tub & yard - RIBryan Properties

13. 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.
The price is AU$1,350
includes taxes & fees
13 Oct - 14 Oct
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

14. 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 AU$896
includes taxes & fees
5 Oct - 6 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

15. Spacious Private Cottage Close to Beaches & Newport

Spacious Private Cottage Close to Beaches & Newport
Middletown
10.0 out of 10, Exceptional, (3 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.
The price is AU$1,886
includes taxes & fees
28 Sept - 29 Sept
Spacious Private Cottage Close to Beaches & Newport

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.
Third Beach Road

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 AU$1,835
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
The price is AU$1,360
includes taxes & fees
7 Oct - 8 Oct
Stepping Stone

19. 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 AU$3,044
includes taxes & fees
19 Sept - 20 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

Solo Fish - Family home, walk to beach and pool!
Middletown
9.0 out of 10, Wonderful, (2 reviews)
"Everything about our stay was perfect. The house was extremely clean and very spacious! We were there celebrating my wedding and hosting many people. All the girls got ready there in the morning and we had so much room! Taking pictures in the home that will last us a lifetime made is super easy due to how clean and modern the home was. We all felt so comfortable there and really enjoyed the backyard as well. We will definitely be coming back!Lastly, the management team was 10/10. They answered...
United States
Jenna M.
The price is AU$2,036
includes taxes & fees
13 Oct - 14 Oct
Solo Fish - Family home, walk to beach and pool!
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

Find out more about Cuttyhunk

Cuttyhunk Holiday Homes information

Number of reviews
496
Accommodation
454 Holiday Homes
Lowest Price
AU$660
Highest Price
AU$3,044

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