Cuttyhunk Vacation Rentals

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Our top choices for Cuttyhunk vacation rentals

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
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.
$397 nightly
The price is $443
May 5 - May 6
Total with taxes and fees
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, (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.
$196 nightly
The price is $218
Apr 23 - Apr 24
Total with taxes and fees
The Charming Gem Near The Water!

Middletown Modern Apartment - RIBryan Property

Middletown Modern Apartment - RIBryan Property
Middletown
9.6 out of 10, Exceptional, (16 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
$356 nightly
The price is $387
Apr 22 - Apr 23
Total with taxes and fees
Middletown Modern Apartment - RIBryan Property

Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.8 out of 10, Exceptional, (12 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveler
$289 nightly
The price is $322
Apr 25 - Apr 26
Total with taxes and fees
Lovely 3 bedroom apartment 3rd floor

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
New Bedford
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.
$279 nightly
The price is $312
Apr 26 - Apr 27
Total with taxes and fees
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

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.
$383 nightly
The price is $437
Apr 22 - Apr 23
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
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.
$382 nightly
The price is $436
Apr 27 - Apr 28
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport

Seapowet suite

Seapowet suite
Tiverton
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful area Wonderful accommodationsPlenty of space and welcoming host! "
United States
Dena E.
$169 nightly
The price is $192
Apr 26 - Apr 27
Total with taxes and fees
Seapowet suite

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (28 reviews)
"Beautiful home with everything you could need. Great location too! "
United States
Luc C.
$536 nightly
The price is $611
Apr 26 - Apr 27
Total with taxes and fees
Beach house walking distance to Second Beach

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic stay! "
United States
Cristin C.
$382 nightly
The price is $436
Apr 27 - Apr 28
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (25 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
$383 nightly
The price is $427
May 4 - May 5
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Dartmouth
$289 nightly
The price is $323
May 6 - May 7
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
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.
$281 nightly
The price is $314
Apr 24 - Apr 25
Total with taxes and fees
Lovely 4- Bedroom apartment for rent

Drift Loft Houseboat

Drift Loft Houseboat
New Bedford
$190 nightly
The price is $212
Apr 27 - Apr 28
Total with taxes and fees
Drift Loft Houseboat

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 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.
$1,085 nightly
The price is $1,212
Apr 22 - Apr 23
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (15 reviews)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
$559 nightly
The price is $608
Apr 22 - Apr 23
Total with taxes and fees
Middletown Bungalow - RIBryan Property

Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (15 reviews)
"Best stay "
United States
Justin R.
$618 nightly
The price is $672
Apr 22 - Apr 23
Total with taxes and fees
Little Creek Retreat - RIBryan Property

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, (215 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
$476 nightly
The price is $545
Apr 27 - Apr 28
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
$822 nightly
The price is $918
May 1 - May 2
Total with taxes and fees
4-bedroom house in lovely Edgartown..Centrally located

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 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.
$800 nightly
The price is $894
Apr 22 - Apr 23
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cuttyhunk vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cuttyhunk in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $545 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cuttyhunk rentals

At Expedia, we put the best Cuttyhunk vacation 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 vacation.

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 vacation rental in Cuttyhunk?

Yes, there are vacation rentals near popular attractions in Cuttyhunk, or you can select a more remote option if you want a relaxing place to stay. Cuttyhunk is known for its beaches.

What are some of the best vacation home rentals in Cuttyhunk?

Luxury Beach House, Easton Point. Ocean Views, 2 Master BRs, Walk to Everything: This vacation home rental near Cuttyhunk is located in the city center and has a furnished patio, a private yard, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a 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 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 larger area.

What’s a vacation rental in Cuttyhunk like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Cuttyhunk. Vacation rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.