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

Search Holiday Homes in Cuttyhunk

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cuttyhunk holiday homes

A water park with a large central pool, multiple slides, and a variety of play structures.

1. 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 £376
includes taxes & fees
30 Sept - 1 Oct
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

2. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is £562
includes taxes & fees
27 Sept - 28 Sept
Backyard Retreat / 5 Min > Beach & Main St
A modern kitchen with white appliances, a teal dining area, and a fireplace.

3. 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 £355
includes taxes & fees
23 Sept - 24 Sept
Ellery Bungalow #49 - Minutes from the Sand
A patio area with wicker chairs, a small table, and a house with a shingled exterior.

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 £355
includes taxes & fees
23 Sept - 24 Sept
Ellery Beach Bungalow #47- Relaxed Island Living
A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

5. 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 £355
includes taxes & fees
23 Sept - 24 Sept
Ellery Bungalow #51- Island Calm Near Newport
A wooden deck with a built-in bench and a small enclosed area with a door.

6. 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 £378
includes taxes & fees
27 Sept - 28 Sept
4br & 2ba Ranch style house w/ huge backyard!
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

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 £523
includes taxes & fees
27 Sept - 28 Sept
Beach house walking distance to Second Beach
A room with a ceiling fan, a blue sofa, a wooden coffee table, a kitchen area with stools, and a view through a window.

8. 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 £377
includes taxes & fees
26 Sept - 27 Sept
Pop, Bubble, and sun-drenched Cutie Cottage!

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 £542
includes taxes & fees
27 Sept - 28 Sept
Little Creek Retreat Private hot tub & yard - RIBryan Properties
A two-story house with a stone chimney, a red front door, and a porch with white railings.

10. 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 £530
includes taxes & fees
23 Sept - 24 Sept
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
A living room with a television, a sofa, a coffee table, and a large window with a view of the outdoors.

11. Delightful, Charming, Oversized 2 bedroom 2 bath Cottage!

Delightful, Charming, Oversized 2 bedroom 2 bath Cottage!
Middletown
9.4 out of 10, Exceptional, (27 reviews)
"Nice place"
United States
Rachael M.
The price is £571
includes taxes & fees
2 Oct - 3 Oct
Delightful, Charming, Oversized 2 bedroom 2 bath Cottage!
A beach with a sandy shore and calm water.

12. 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 £658
includes taxes & fees
28 Sept - 29 Sept
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
A dining area with a table set for six, a chandelier, and large windows offering a view of the outdoors.

13. 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 £774
includes taxes & fees
28 Sept - 29 Sept
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow
A spacious living area with a high ceiling, a dining table, and a kitchen area.

14. 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 £812
includes taxes & fees
4 Oct - 5 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A single-story house with a grey siding exterior, a front door with a blue doorbell, and a small front yard with a gravel pathway and various plants.

15. 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 £348
includes taxes & fees
29 Sept - 30 Sept
Ellery Beach Bungalow #45- A Refined Island Escape
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

16. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
The price is £631
includes taxes & fees
4 Oct - 5 Oct
Oak Bluffs 4BR • 5 Min Drive to Downtown
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

17. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is £692
includes taxes & fees
25 Sept - 26 Sept
Walk to Beach! Oak Bluffs Home & Studio
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

18. 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, (223 reviews)
"Great location "
United States
Stephanie B.
The price is £436
includes taxes & fees
18 Oct - 19 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

19. 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 £1,019
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A modern kitchen with a stainless steel refrigerator, wooden dining table, and light-colored flooring.

20. Spacious Private Cottage Close to Beaches & Newport

Spacious Private Cottage Close to Beaches & Newport
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"One of the best VRBO properties we’ve ever stayed at!"
United States
jeffrey w.
The price is £972
includes taxes & fees
23 Sept - 24 Sept
Spacious Private Cottage Close to Beaches & Newport
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cuttyhunk Hotel Reviews

Residence Inn by Marriott New Bedford Dartmouth

Residence Inn by Marriott New Bedford Dartmouth

10/10 Excellent
"Try the top air bus tour."
Jan 1-night trip
Posted 3 hours ago
Residence Inn by Marriott New Bedford Dartmouth

Find out more about Cuttyhunk

Cuttyhunk Holiday Homes information

Number of reviews
513
Accommodation
440 Holiday Homes
Lowest Price
£348
Highest Price
£1,019

Explore a world of travel with Expedia