Cuttyhunk Vacation Rentals

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Our top choices for Cuttyhunk vacation rentals

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Dartmouth
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
$1,252 nightly
The price is $1,399
Feb 19 - Feb 20
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Blue Haven Houseboat

Blue Haven Houseboat
New Bedford
$150 nightly
The price is $168
Mar 1 - Mar 2
Total with taxes and fees
Blue Haven Houseboat

Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (14 reviews)
"Best stay "
United States
Justin R.
$614 nightly
The price is $667
Feb 19 - Feb 20
Total with taxes and fees
Little Creek Retreat - RIBryan Property

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.
$387 nightly
The price is $432
Feb 24 - Feb 25
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.

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
Feb 19 - Feb 20
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
$971 nightly
The price is $1,085
Feb 20 - Feb 21
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Allston Greens

Allston Greens
Middletown
10.0 out of 10, Exceptional, (9 reviews)
"Great location and perfect layout of the home for our needs"
United States
Anna P.
$839 nightly
The price is $957
Feb 19 - Feb 20
Total with taxes and fees
Allston Greens

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
Feb 19 - Feb 20
Total with taxes and fees
A NOSTALGIC SPACE! 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 reviews)
"Great stay! Great property!"
United States
Liz A.
$1,772 nightly
The price is $1,873
Mar 9 - Mar 10
Total with taxes and fees
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (14 reviews)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
$527 nightly
The price is $573
Feb 19 - Feb 20
Total with taxes and fees
Middletown Bungalow - RIBryan Property

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (34 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.
$200 nightly
The price is $223
Feb 19 - Feb 20
Total with taxes and fees
The Charming Gem Near The Water!

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
$596 nightly
The price is $666
Feb 21 - Feb 22
Total with taxes and fees
Oak Bluffs - Quiet neighborhood

Third Beach Road

Third Beach Road
Middletown
6.0 out of 10, (1 review)
"Renovated house, very cute. Kitchen was definitely a highlight as it was a good space for cooking and gathering together. Some amenities of house were not exactly as listed in description. Location of house was nice-close to beach and park with pickleball courts, easy access to Newport wharves and restaurants "
United States
Janet S.
$1,324 nightly
The price is $1,509
Feb 19 - Feb 20
Total with taxes and fees
Third Beach Road

Seapowet suite

Seapowet suite
Tiverton
9.8 out of 10, Exceptional, (8 reviews)
"Adequate for one night. Host friendly."
United States
Louise
$100 nightly
The price is $114
Feb 19 - Feb 20
Total with taxes and fees
Seapowet suite

Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"Great location, clean house. Well stocked with supplies and beach items."
United States
Tyler M.
$332 nightly
The price is $371
Mar 15 - Mar 16
Total with taxes and fees
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Spectacular View from Rooftop Deck | Sleeps 12

Spectacular View from Rooftop Deck | Sleeps 12
Easton's Point
10.0 out of 10, Exceptional, (1 review)
"After finding out we had booked hotel rooms with the wrong hotel there were no rooms available last minute for a group of six. Stay Newport was able to get us in last minute and the lodging was wonderful. Very responsive communication. Great location. Very clean and well taken care of property. We wish we could have stayed for a few more days!"
United States
Devon D.
$1,465 nightly
The price is $1,670
Feb 19 - Feb 20
Total with taxes and fees
Spectacular View from Rooftop Deck | Sleeps 12

Double lot walk to beach 5 bed 7 bath, large yard

Double lot walk to beach 5 bed 7 bath, large yard
Easton's Point
9.8 out of 10, Exceptional, (26 reviews)
"We enjoyed our stay at the home. Very well maintained."
United States
Anmol P.
$1,353 nightly
The price is $1,543
Feb 19 - Feb 20
Total with taxes and fees
Double lot walk to beach 5 bed 7 bath, large yard

Walk to beach corner lot, 5 bed large yard

Walk to beach corner lot, 5 bed large yard
Middletown
$2,507 nightly
The price is $2,858
Feb 19 - Feb 20
Total with taxes and fees
Walk to beach corner lot, 5 bed large yard

Between Beaches

Between Beaches
Easton's Point
8.0 out of 10, Very Good, (1 review)
$585 nightly
The price is $667
Feb 19 - Feb 20
Total with taxes and fees
Between Beaches

Solo Fish - Family home, walk to beach and pool!

Solo Fish - Family home, walk to beach and pool!
Middletown
9.0 out of 10, Wonderful, (2 reviews)
"Everything about our stay was perfect. The house was extremely clean and very spacious! We were there celebrating my wedding and hosting many people. All the girls got ready there in the morning and we had so much room! Taking pictures in the home that will last us a lifetime made is super easy due to how clean and modern the home was. We all felt so comfortable there and really enjoyed the backyard as well. We will definitely be coming back!Lastly, the management team was 10/10. They answered...
United States
Jenna M.
$1,195 nightly
The price is $1,363
Mar 17 - Mar 18
Total with taxes and fees
Solo Fish - Family home, walk to beach and pool!
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 $422 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?

9-bedroom vacation home near Cape Cod Beaches: This vacation home rental near Cuttyhunk is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so 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 Demarest Lloyd State Park 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.