Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Find holiday rentals that suit your style
Aparthotels
Apartments
Our top choices for Cuttyhunk holiday homes
1. Backyard Retreat / 5 Min > Beach & Main St
Backyard Retreat / 5 Min > Beach & Main StFairhaven
The price is NZ$1,008
includes taxes & fees
11 Nov - 12 Nov
2. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MADartmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
richard m.
The price is NZ$517
includes taxes & fees
13 Nov - 14 Nov
3. 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."
Lauren F.
The price is NZ$849
includes taxes & fees
30 Nov - 1 Dec
4. Beach house walking distance to Second Beach
Beach house walking distance to Second BeachEaston's Point
10.0 out of 10, Exceptional, (38 reviews)
"Ideal property to enjoy all Middletown & Newport have to offer!"
kelly k.
The price is NZ$889
includes taxes & fees
18 Nov - 19 Nov
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. "
Emo C.
The price is NZ$1,068
includes taxes & fees
11 Nov - 12 Nov
6. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan
9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryanMiddletown
10.0 out of 10, Exceptional, (17 reviews)
"Best stay "
Justin R.
The price is NZ$1,202
includes taxes & fees
16 Nov - 17 Nov
7. 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."
David C.
The price is NZ$880
includes taxes & fees
16 Nov - 17 Nov
8. Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs 4BR • 5 Min Drive to DowntownOak 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!"
Chris S.
The price is NZ$1,235
includes taxes & fees
24 Nov - 25 Nov
9. Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan
Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryanMiddletown
9.6 out of 10, Exceptional, (19 reviews)
"Great house and easy ride to everything in Newport!"
Terry S.
The price is NZ$1,282
includes taxes & fees
16 Nov - 17 Nov
10. Third Beach Road
Third Beach RoadMiddletown
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 "
Janet S.
The price is NZ$2,721
includes taxes & fees
11 Nov - 12 Nov
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 BeachFalmouth
10.0 out of 10, Exceptional, (227 reviews)
"Great location "
Stephanie B.
The price is NZ$886
includes taxes & fees
8 Dec - 9 Dec
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"
Eli R.
The price is NZ$1,105
includes taxes & fees
11 Nov - 12 Nov
13. Spacious Private Cottage Close to Beaches & Newport
Spacious Private Cottage Close to Beaches & NewportMiddletown
9.6 out of 10, Exceptional, (4 reviews)
"One of the best VRBO properties we’ve ever stayed at!"
jeffrey w.
The price is NZ$2,106
includes taxes & fees
11 Nov - 12 Nov
14. Spectacular View from Rooftop Deck | Sleeps 12
Spectacular View from Rooftop Deck | Sleeps 12Easton's Point
8.0 out of 10, Very good, (3 reviews)
"Plenty of room, beautifully appointed. As advertised."
Gerald L.
The price is NZ$2,998
includes taxes & fees
11 Nov - 12 Nov
15. Walk to beach corner lot, 5 bed large yard
Walk to beach corner lot, 5 bed large yardMiddletown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place. Clean and well kept"
Michael G.
The price is NZ$2,426
includes taxes & fees
11 Nov - 12 Nov
16. Beautiful Estate with salt water pool & pond with kayaks
Beautiful Estate with salt water pool & pond with kayaksOak 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."
Lamar A.
The price is NZ$5,343
includes taxes & fees
30 Nov - 1 Dec
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."
Rosie G.
The price is NZ$2,374
includes taxes & fees
11 Nov - 12 Nov
18. Double lot walk to beach 5 bed 7 bath, large yard
Double lot walk to beach 5 bed 7 bath, large yardEaston'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!"
Lynn J.
The price is NZ$2,807
includes taxes & fees
11 Nov - 12 Nov
19. Walk to Beach! Oak Bluffs Home & Studio
Walk to Beach! Oak Bluffs Home & StudioOak Bluffs
The price is NZ$1,501
includes taxes & fees
11 Nov - 12 Nov
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.
Learn more about Cuttyhunk
Come to relaxing Cuttyhunk and enjoy its kayaking, history and beaches.
Top reviews in Cuttyhunk
Delano Homestead Bed & Breakfast
Delano Homestead Bed & BreakfastFairhaven
10/10 Excellent
We were pleasantly surprised at the historic nature of the B&B and the ambience of it, beautiful antiques and stylish decoration. Host was very welcoming and extra helpful re nearby ferry service from New Bedford to Martha's Vineyard. His knowledge allowed us to make the most of our stay on the island. Plentiful breakfast provided.
Helen
