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.
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.
$351 nightly
The price is $392
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.

Seapowet suite

Seapowet suite
Tiverton
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
$100 nightly
The price is $110
Jan 1 - Jan 2, 2026
Total with taxes and fees
Seapowet suite

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.
$200 nightly
The price is $223
Jan 22 - Jan 23, 2026
Total with taxes and fees
The Charming Gem Near The Water!

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.
$312 nightly
The price is $349
Dec 31 - Jan 1, 2026
Total with taxes and fees
Lovely 4- Bedroom apartment for rent

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.
$397 nightly
The price is $450
Jan 20 - Jan 21, 2026
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

Blue Haven Houseboat

Blue Haven Houseboat
2.0 star property
New Bedford
$124 nightly
The price is $139
Jan 6 - Jan 7, 2026
Total with taxes and fees
Blue Haven Houseboat

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.
$394 nightly
The price is $446
Jan 4 - Jan 5, 2026
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)
"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.
$396 nightly
The price is $449
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport

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.
$1,629 nightly
The price is $1,722
Jan 13 - Jan 14, 2026
Total with taxes and fees
The Beach Estate, Panoramic Ocean Views, 5700 sqft

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

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

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.
Cozy efficiency apartment/heated pool

Between Beaches

Between Beaches
Easton's Point
8.0 out of 10, Very Good, (1)
$590 nightly
The price is $669
Jan 2 - Jan 3, 2026
Total with taxes and fees
Between Beaches

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.
$503 nightly
The price is $553
Jan 1 - Jan 2, 2026
Total with taxes and fees
Beach house walking distance to Second Beach

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)
"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.
$1,293 nightly
The price is $1,444
Jan 4 - Jan 5, 2026
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

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.
$800 nightly
The price is $894
Dec 31 - Jan 1, 2026
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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.
$354 nightly
The price is $383
Jan 1 - Jan 2, 2026
Total with taxes and fees
Middletown Modern Apartment - RIBryan Property

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.
$1,085 nightly
The price is $1,212
Dec 31 - Jan 1, 2026
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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.
$432 nightly
The price is $494
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

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.
$971 nightly
The price is $1,085
Jan 1 - Jan 2, 2026
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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)
"We enjoyed our stay at the home. Very well maintained."
United States
Anmol P.
$1,357 nightly
The price is $1,539
Jan 5 - Jan 6, 2026
Total with taxes and fees
Double lot walk to beach 5 bed 7 bath, large yard
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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: 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. 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 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.