Cuttyhunk Holiday Rentals

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Holiday Rentals in Cuttyhunk

Cottage in Dartmouth

2.0 star property
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is AU$643
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottage overlooking the bay in Padanaram Village.

Apartment in New Bedford

9.6 out of 10, Exceptional, (34)
"I had stayed here last year and it's so close to several of my family members. This is my go to place when I travel to the New Bedford area."
United States
Judy C.
The price is AU$360
includes taxes & fees
15 Dec - 16 Dec
The Charming Gem Near The Water!

Holiday Home in Middletown

10.0 out of 10, Exceptional, (1)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is AU$666
includes taxes & fees
7 Dec - 8 Dec
Ellery Beach Bungalow #45- A Refined Island Escape

Apartment in Tiverton

9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
The price is AU$273
includes taxes & fees
3 Jan - 4 Jan 2026
Seapowet suite

Holiday Home in Middletown

10.0 out of 10, Exceptional, (4)
"Fantastic stay! "
United States
Cristin C.
The price is AU$666
includes taxes & fees
4 Dec - 5 Dec
Ellery Beach Bungalow #47- Relaxed Island Living

Holiday Home in Middletown

9.6 out of 10, Exceptional, (94)
"My family had an amazing stay at this bungalow. It is very clean and offered everything we needed for our stay in Newport. The beach is very close and there are plenty of restaurants and convenience store within walking distance. "
United States
Tamara C.
The price is AU$680
includes taxes & fees
17 Dec - 18 Dec
Ellery Bungalow #51- Island Calm Near Newport

Holiday Home in New Bedford

2.0 star property
The price is AU$214
includes taxes & fees
16 Dec - 17 Dec
Blue Haven Houseboat

Holiday Home in Falmouth

10.0 out of 10, Exceptional, (209)
"We had a great stay. House is spacious, clean and well-stocked with everything we needed. We loved that we were able to walk to downtown shops and restaurants, the ferry to Martha’s Vineyard and the beach. Would definitely stay here again. "
United States
Ava B.
The price is AU$761
includes taxes & fees
10 Dec - 11 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Holiday Home in Dartmouth

The price is AU$470
includes taxes & fees
9 Dec - 10 Dec
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Holiday Home in Westport

9.8 out of 10, Exceptional, (22)
"Beautiful house! Had a wonderful time!"
United States
RYAN S.
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Apartment in Middletown

9.6 out of 10, Exceptional, (16)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is AU$591
includes taxes & fees
14 Dec - 15 Dec
Middletown Modern Apartment - RIBryan Property

Holiday Home in Easton's Point

8.0 out of 10, Very good, (1)
The price is AU$1,027
includes taxes & fees
4 Dec - 5 Dec
Between Beaches

Apartment in Chilmark

9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
The price is AU$708
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy efficiency apartment/heated pool

Holiday Home in Middletown

9.4 out of 10, Exceptional, (14)
"Great place! So many bedrooms! Nice private yard, great if you have a dog. Had a wonderful stay, would stay again. Close enough to Newport to drive in and out no problem, plus close to beaches. "
United States
Todd C.
The price is AU$1,026
includes taxes & fees
4 Dec - 5 Dec
Little Creek Retreat - RIBryan Property

Holiday Home in Easton's Point

9.8 out of 10, Exceptional, (26)
"What a great location, well appointed home, and a very professional VRBO host. You know that love and care goes into making guests feel welcomed and special. Lots of amenities and space to make your stay memorable. "
United States
Victoria L.
The price is AU$907
includes taxes & fees
4 Dec - 5 Dec
Beach house walking distance to Second Beach

Holiday Home in Tisbury

10.0 out of 10, Exceptional, (16)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is AU$1,668
includes taxes & fees
23 Dec - 24 Dec
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Holiday Home in Oak Bluffs

9.4 out of 10, Exceptional, (3)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is AU$1,374
includes taxes & fees
4 Dec - 5 Dec
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Holiday Home in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is AU$1,864
includes taxes & fees
7 Dec - 8 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Holiday Home in Middletown

9.4 out of 10, Exceptional, (13)
"Very clean and roomy for our 8 guests. Perfect location for access to Second Beach and downtown Newport."
United States
William H.
The price is AU$970
includes taxes & fees
17 Dec - 18 Dec
Middletown Bungalow - RIBryan Property

Holiday Home in Middletown

10.0 out of 10, Exceptional, (1)
"Had a wonderful stay; loved that it was within walking distance to great places to eat and also the beach.Everything was clean and cozy. I highly recommend it if you would like to check out Newport and the surrounding towns.Owners were very responsive if needed. We loved our trip!"
United States
Cheryl H.
The price is AU$695
includes taxes & fees
17 Dec - 18 Dec
Ellery Bungalow #49 - Minutes from the Sand
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 AU$970 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. 

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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Cuttyhunk is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Gooseberry Island 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.