Holiday Rentals in Cuttyhunk

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Our top choices for Cuttyhunk holiday rentals

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is €329
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottage overlooking the bay in Padanaram Village.

The Charming Gem Near The Water!

The Charming Gem Near The Water!
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 €194
includes taxes & fees
4 Jan - 5 Jan 2026
The Charming Gem Near The Water!

Blue Haven Houseboat

Blue Haven Houseboat
2.0 star property
New Bedford
Blue Haven Houseboat

Seapowet suite

Seapowet suite
Tiverton
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
The price is €97
includes taxes & fees
3 Jan - 4 Jan 2026
Seapowet suite

Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape
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 €379
includes taxes & fees
13 Jan - 14 Jan 2026
Ellery Beach Bungalow #45- A Refined Island Escape

Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
9.0 out of 10, Wonderful, (2)
"My friend and I were looking for a place to stay for a last minute day-trip to Nantucket. This property was great for that purpose and Angelino was a very responsive host. One thing to note is that while there is plenty of free street parking, there is no onsite parking even though we were told there was one spot available. I think this might have been due to some confusion regarding which property we had actually booked."
United States
Elizabeth C.
The price is €305
includes taxes & fees
22 Dec - 23 Dec
Lovely 4- Bedroom apartment for rent

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
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 €393
includes taxes & fees
13 Jan - 14 Jan 2026
Ellery Bungalow #51- Island Calm Near Newport

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
10.0 out of 10, Exceptional, (4)
"Fantastic stay! "
United States
Cristin C.
The price is €391
includes taxes & fees
13 Jan - 14 Jan 2026
Ellery Beach Bungalow #47- Relaxed Island Living

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA
Dartmouth
The price is €267
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

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, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is €432
includes taxes & fees
22 Dec - 23 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
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 €485
includes taxes & fees
1 Jan - 2 Jan 2026
Beach house walking distance to Second Beach

Middletown Modern Apartment - RIBryan Property

Middletown Modern Apartment - RIBryan Property
Middletown
9.6 out of 10, Exceptional, (16)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is €337
includes taxes & fees
22 Dec - 23 Dec
Middletown Modern Apartment - RIBryan Property

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
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 €950
includes taxes & fees
30 Dec - 31 Dec
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Between Beaches

Between Beaches
Easton's Point
8.0 out of 10, Very good, (1)
The price is €585
includes taxes & fees
28 Dec - 29 Dec
Between Beaches

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
The price is €403
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy efficiency apartment/heated pool

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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 €783
includes taxes & fees
22 Dec - 23 Dec
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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 €1,062
includes taxes & fees
22 Dec - 23 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft
Mattapoisett
9.8 out of 10, Exceptional, (8)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
United States
Catherine T.
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property
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 €585
includes taxes & fees
29 Dec - 30 Dec
Little Creek Retreat - RIBryan Property

Stones Throw Waterfront

Stones Throw Waterfront
Dartmouth
8.8 out of 10, Excellent, (6)
"Perfect spot for our long weekend visiting local family and we wish we could have stayed longer. Close to the village, kayaks on site/ water view- house clean and decorated thoughtfully. Pet friendly, we brought our small dog. The outdoor shower is a must try! We hope to be back soon! "
United States
Lauren G.
The price is €540
includes taxes & fees
3 Jan - 4 Jan 2026
Stones Throw Waterfront
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, apart-hotels, 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 favorite 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 depends 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 €540 per night. Entering your travel dates in the search wizard you might find 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 Chilmark Chocolates, 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.