Cuttyhunk Vacation Rentals

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Our top choices for Cuttyhunk vacation rentals

Blue Haven Houseboat

Blue Haven Houseboat
2.0 star property
New Bedford
$124 nightly
The price is $139
Jan 14 - Jan 15
Total with taxes and fees
Blue Haven Houseboat

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.
$199 nightly
The price is $222
Jan 18 - Jan 19
Total with taxes and fees
The Charming Gem Near The Water!

Seapowet suite

Seapowet suite
Tiverton
9.8 out of 10, Exceptional, (7 reviews)
"Adequate for one night. Host friendly."
United States
Louise
$100 nightly
The price is $114
Jan 13 - Jan 14
Total with taxes and fees
Seapowet suite

Spacious 3 bedroom 1st Floor closeby attractions

Spacious 3 bedroom 1st Floor closeby attractions
New Bedford
10.0 out of 10, Exceptional, (25 reviews)
"Enjoyed the stay good location nice place overall"
United States
Jeff B.
Spacious 3 bedroom 1st Floor closeby attractions

Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
9.0 out of 10, Wonderful, (2 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.
$304 nightly
The price is $340
Jan 13 - Jan 14
Total with taxes and fees
Lovely 4- Bedroom apartment for rent

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.
$381 nightly
The price is $435
Jan 13 - Jan 14
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape

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.
Middletown Modern Apartment - RIBryan Property

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.
$381 nightly
The price is $435
Jan 13 - Jan 14
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

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 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.
$421 nightly
The price is $470
Feb 1 - Feb 2
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (94 reviews)
"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.
$381 nightly
The price is $435
Jan 13 - Jan 14
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport

Between Beaches

Between Beaches
Easton's Point
8.0 out of 10, Very Good, (1 review)
$590 nightly
The price is $672
Jan 13 - Jan 14
Total with taxes and fees
Between Beaches

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 reviews)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
$432 nightly
The price is $494
Jan 13 - Jan 14
Total with taxes and fees
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 reviews)
"The house was clean, had every thing you could possibly need. Great location."
United States
Sarah S.
$502 nightly
The price is $572
Jan 19 - Jan 20
Total with taxes and fees
Beach house walking distance to Second Beach

Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (14 reviews)
"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.
$618 nightly
The price is $672
Jan 13 - Jan 14
Total with taxes and fees
Little Creek Retreat - RIBryan Property

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.
$528 nightly
The price is $574
Jan 13 - Jan 14
Total with taxes and fees
Middletown Bungalow - RIBryan Property

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)
"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.
$1,573 nightly
The price is $1,663
Feb 11 - Feb 12
Total with taxes and fees
The Beach Estate, Panoramic Ocean Views, 5700 sqft

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
Jan 13 - Jan 14
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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.
$848 nightly
The price is $967
Jan 13 - Jan 14
Total with taxes and fees
Allston Greens

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)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
$971 nightly
The price is $1,085
Jan 14 - Jan 15
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Drift Loft Houseboat

Drift Loft Houseboat
2.0 star property
New Bedford
$161 nightly
The price is $180
Jan 14 - Jan 15
Total with taxes and fees
Drift Loft Houseboat
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 $1,212 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?

MOST CHIC SPOT! Your Martha's Vineyard Getaway!: This vacation home rental near Cuttyhunk is located in the city center and has a patio, a garden, 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.

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 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.