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

Cuttyhunk Holiday Rentals

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Our top choices for Cuttyhunk holiday rentals

1. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is AU$731
includes taxes & fees
22 Oct - 23 Oct
Charming cottage overlooking the bay in Padanaram Village.

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is AU$889
includes taxes & fees
19 Oct - 20 Oct
Backyard Retreat / 5 Min > Beach & Main St

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)
"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$804
includes taxes & fees
31 Oct - 1 Nov
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

4. 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, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is AU$441
includes taxes & fees
22 Oct - 23 Oct
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

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 AU$863
includes taxes & fees
18 Oct - 19 Oct
4br & 2ba Ranch style house w/ huge backyard!

6. Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.4 out of 10, Exceptional, (13 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveller
The price is AU$538
includes taxes & fees
29 Oct - 30 Oct
Lovely 3 bedroom apartment 3rd floor

7. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (33 reviews)
"Fabulous property! Clean and very comfy."
United States
Claudia
The price is AU$754
includes taxes & fees
18 Oct - 19 Oct
Brand new! Lovely apartment-Vineyard Haven

8. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is AU$1,525
includes taxes & fees
18 Oct - 19 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is AU$1,612
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs

10. 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 AU$924
includes taxes & fees
19 Oct - 20 Oct
9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

11. Seapowet suite

Seapowet suite
Tiverton
9.0 out of 10, Wonderful, (15 reviews)
"Beautiful area Wonderful accommodationsPlenty of space and welcoming host! "
United States
Dena E.
The price is AU$363
includes taxes & fees
1 Nov - 2 Nov
Seapowet suite

12. 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)
"Great place and very welcoming host. Nearby to second beach in a quiet neighborhood."
United States
Melissa G.
The price is AU$907
includes taxes & fees
25 Oct - 26 Oct
Beach house walking distance to Second Beach

13. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (47 reviews)
"Lovely flat in a convenient part of town with lots of supermarket and facilities nearby. We loved our stay."
United States
Thomas C.
The price is AU$323
includes taxes & fees
18 Oct - 19 Oct
The Charming Gem Near The Water!

14. 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 AU$999
includes taxes & fees
21 Oct - 22 Oct
Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan

15. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is AU$855
includes taxes & fees
24 Oct - 25 Oct
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

16. Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan

Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan
Middletown
9.6 out of 10, Exceptional, (21 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is AU$642
includes taxes & fees
18 Oct - 19 Oct
Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan

17. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (98 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is AU$675
includes taxes & fees
19 Oct - 20 Oct
Ellery Bungalow #51- Island Calm Near Newport

18. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
The price is AU$485
includes taxes & fees
12 Nov - 13 Nov
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

19. 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$665
includes taxes & fees
18 Oct - 19 Oct
Ellery Bungalow #49 - Minutes from the Sand

20. 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$1,401
includes taxes & fees
19 Oct - 20 Oct
Stepping Stone
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

Everything you need to know about Cuttyhunk holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cuttyhunk holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cuttyhunk holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cuttyhunk. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cuttyhunk holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cuttyhunk rentals

At Expedia, we put the best Cuttyhunk holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cuttyhunk rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cuttyhunk holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cuttyhunk. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find a holiday rental in Cuttyhunk?

Yes, there are holiday rentals close to the most popular sights in Cuttyhunk, or you can select a more secluded option if you're looking for a relaxing stay. Cuttyhunk is known for its beaches.

What are some of the best holiday rentals that Cuttyhunk has to offer?

Quaint, ranch style home in Oak Bluffs with central air: This holiday home rental outside of Cuttyhunk is located near the beach, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Cuttyhunk?

Explore the area and family-friendly sights such as Buttonwood Park Zoo, or get out into nature at a spot like Aquinnah Cliffs. Gay Head Lighthouse and Horseneck Beach State Reservation are a couple of places you'll find in the wider area.

What’s a holiday rental in Cuttyhunk like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cuttyhunk. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.