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 571
AED 2,095 total
includes taxes & fees
4 Nov - 5 Nov
Backyard Retreat / 5 Min > Beach & Main St

2. 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 1,075 total
includes taxes & fees
13 Nov - 14 Nov
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

3. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (37 reviews)
"Ideal property to enjoy all Middletown & Newport have to offer!"
United States
kelly k.
The price is AED 261
AED 1,776 total
includes taxes & fees
4 Nov - 5 Nov
Beach house walking distance to Second Beach

4. 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)
"Beautiful and relaxing location."
United States
Lauren F.
The price is AED 826
AED 1,760 total
includes taxes & fees
30 Nov - 1 Dec
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

5. 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 1,102
AED 2,169 total
includes taxes & fees
4 Dec - 5 Dec
4br & 2ba Ranch style house w/ huge backyard!

6. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan
Middletown
9.6 out of 10, Exceptional, (18 reviews)
"Best stay "
United States
Justin R.
The price is AED 2,508
AED 3,879 total
includes taxes & fees
4 Dec - 5 Dec
9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

7. Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan

Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan
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 1,494
AED 2,797 total
includes taxes & fees
8 Nov - 9 Nov
Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan

8. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is AED 841
AED 1,645 total
includes taxes & fees
11 Nov - 12 Nov
Vineyard Luxury "Yurt"

9. 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 988
AED 2,536 total
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

10. 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

11. 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, (227 reviews)
"Great location "
United States
Stephanie B.
The price is AED 661
AED 1,921 total
includes taxes & fees
4 Nov - 5 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

12. 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 966
AED 2,261 total
includes taxes & fees
4 Nov - 5 Nov
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

13. 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

14. Spectacular View from Rooftop Deck | Sleeps 12

Spectacular View from Rooftop Deck | Sleeps 12
Easton's Point
8.0 out of 10, Very good, (3 reviews)
"Plenty of room, beautifully appointed. As advertised."
United States
Gerald L.
Spectacular View from Rooftop Deck | Sleeps 12

15. 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, (3 reviews)
"Awesome place. Clean and well kept"
United States
Michael G.
Walk to beach corner lot, 5 bed large yard

16. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (17 reviews)
"We had a family reunion and 75 Locust Street was the central hub of the four night stay. The house is beautiful, clean and we had family from all over stay there. We'd go back in a heartbeat. Easy access to downtown and the hosts were communicative and informative."
United States
Melissa L.
The price is AED 1,636
AED 4,076 total
includes taxes & fees
4 Nov - 5 Nov
Beautiful Home in Falmouth Village

17. 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.
Solo Fish - Family home, walk to beach and pool!

18. 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 7,346
AED 11,131 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful Estate with salt water pool & pond with kayaks

19. Double lot walk to beach 5 bed 7 bath, large yard

Double lot walk to beach 5 bed 7 bath, large yard
Easton's Point
9.6 out of 10, Exceptional, (29 reviews)
"Excellent property in an excellent location. The host was great and very communicative. 10/10 would recommend!"
United States
Lynn J.
Double lot walk to beach 5 bed 7 bath, large yard

20. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AED 1,142
AED 3,003 total
includes taxes & fees
4 Nov - 5 Nov
Walk to Beach! Oak Bluffs Home & Studio
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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