Holiday Rentals in Cuttyhunk

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Our top choices for Cuttyhunk holiday rentals

10.0 out of 10, Exceptional, (17 reviews)
"Great location, clean house. Well stocked with supplies and beach items."
United States
Tyler M.
The price is €310
includes taxes & fees
25 Mar - 26 Mar
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Apartment in New Bedford

Lovely 3 bedroom apartment for rent
9.8 out of 10, Exceptional, (12 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveller
The price is €266
includes taxes & fees
22 Mar - 23 Mar
Lovely 3 bedroom apartment for rent

Holiday Home in New Bedford

Blue Haven Houseboat
The price is €149
includes taxes & fees
30 Mar - 31 Mar
Blue Haven Houseboat
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "
United States
ralpjh c.
The price is €374
includes taxes & fees
23 Mar - 24 Mar
Charming cottage overlooking the bay in Padanaram Village.
9.6 out of 10, Exceptional, (94 reviews)
"This was the perfect size and location for our group of 5, would definitely stay again! "
United States
toni g.
The price is €376
includes taxes & fees
31 Mar - 1 Apr
Ellery Bungalow #51- Island Calm Near Newport

Apartment in New Bedford

The Charming Gem Near The Water!
9.6 out of 10, Exceptional, (35 reviews)
"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 €198
includes taxes & fees
7 Apr - 8 Apr
The Charming Gem Near The Water!
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 €390
includes taxes & fees
13 Apr - 14 Apr
Ellery Beach Bungalow #45- A Refined Island Escape
9.6 out of 10, Exceptional, (10 reviews)
"We love it here quite neighbors are really nice Angelino is on top of everything great host "
United States
Joann E.
The price is €283
includes taxes & fees
22 Mar - 23 Mar
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Apartment in Tiverton

Seapowet suite
9.8 out of 10, Exceptional, (9 reviews)
"Adequate for one night. Host friendly."
United States
Louise
The price is €160
includes taxes & fees
22 Mar - 23 Mar
Seapowet suite

Holiday Home in Easton's Point

Beach house walking distance to Second Beach
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful home with everything you could need. Great location too! "
United States
Luc C.
The price is €435
includes taxes & fees
23 Mar - 24 Mar
Beach house walking distance to Second Beach
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is €398
includes taxes & fees
22 Mar - 23 Mar
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
9.6 out of 10, Exceptional, (16 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is €361
includes taxes & fees
19 Apr - 20 Apr
Middletown Modern Apartment - RIBryan Property
10.0 out of 10, Exceptional, (4 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.
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Apartment in New Bedford

Lovely 4- Bedroom apartment for rent
6.8 out of 10, (3 reviews)
"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 €262
includes taxes & fees
22 Mar - 23 Mar
Lovely 4- Bedroom apartment for rent
10.0 out of 10, Exceptional, (7 reviews)
"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 €1,053
includes taxes & fees
22 Mar - 23 Mar
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic stay! "
United States
Cristin C.
The price is €391
includes taxes & fees
13 Apr - 14 Apr
Ellery Beach Bungalow #47- Relaxed Island Living
9.4 out of 10, Exceptional, (3 reviews)
"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 €765
includes taxes & fees
24 Mar - 25 Mar
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Holiday Home in Middletown

Middletown Bungalow - RIBryan Property
9.4 out of 10, Exceptional, (14 reviews)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
The price is €486
includes taxes & fees
22 Mar - 23 Mar
Middletown Bungalow - RIBryan Property

Holiday Home in Oak Bluffs

Oak Bluffs - Quiet neighborhood
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
Oak Bluffs - Quiet neighborhood
10.0 out of 10, Exceptional, (26 reviews)
"Enjoyed the stay good location nice place overall"
United States
Jeff B.
The price is €271
includes taxes & fees
18 Apr - 19 Apr
Spacious 3 bedroom 1st Floor closeby attractions
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 €160 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?

Luxury Beach House, Easton Point. Ocean Views, 2 Master BRs, Walk to Everything: This holiday home rental outside of Cuttyhunk is located in the city centre, and has a furnished patio, a private garden and a BBQ 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. You can relax into your holiday with 1 hot tub and a selection of books.

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.