Cuttyhunk Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Cuttyhunk

Fridge, microwave, oven, stovetop
The Charming Gem Near The Water!

Apartment in 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.
$210 nightly
The price is $235
Dec 9 - Dec 10
Total with taxes and fees
The Charming Gem Near The Water!
On the beach, sun loungers, beach towels
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Vacation Home in Dartmouth

10.0 out of 10, Exceptional, (17)
"Property ideal for our needs of visiting family and meeting our first grandchild "
United States
Carol M.
$324 nightly
The price is $362
Dec 1 - Dec 2
Total with taxes and fees
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
Marina
Charming cottage overlooking the bay in Padanaram Village.

Cottage in Dartmouth

2.0 star property
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
$387 nightly
The price is $432
Dec 1 - Dec 2
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
Fridge, microwave, oven, stovetop
Ellery Bungalow #49 - Minutes from the Sand

Vacation Home in Middletown

10.0 out of 10, Exceptional, (1)
"Had a wonderful stay; loved that it was within walking distance to great places to eat and also the beach.Everything was clean and cozy. I highly recommend it if you would like to check out Newport and the surrounding towns.Owners were very responsive if needed. We loved our trip!"
United States
Cheryl H.
$382 nightly
The price is $433
Nov 30 - Dec 1
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand
Exterior
Seapowet suite

Apartment in Tiverton

9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
$175 nightly
The price is $188
Nov 30 - Dec 1
Total with taxes and fees
Seapowet suite
TV
Blue Haven Houseboat

Vacation Home in New Bedford

2.0 star property
$124 nightly
The price is $139
Dec 1 - Dec 2
Total with taxes and fees
Blue Haven Houseboat
Interior
Ellery Beach Bungalow #47- Relaxed Island Living

Vacation Home in Middletown

10.0 out of 10, Exceptional, (4)
"Fantastic stay! "
United States
Cristin C.
$382 nightly
The price is $433
Nov 30 - Dec 1
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living
Fridge, microwave, oven, stovetop
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Vacation Home in Dartmouth

$274 nightly
The price is $306
Nov 30 - Dec 1
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Vacation Home in Falmouth

10.0 out of 10, Exceptional, (209)
"We had a great stay. House is spacious, clean and well-stocked with everything we needed. We loved that we were able to walk to downtown shops and restaurants, the ferry to Martha’s Vineyard and the beach. Would definitely stay here again. "
United States
Ava B.
$433 nightly
The price is $496
Nov 30 - Dec 1
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Interior
Ellery Bungalow #51- Island Calm Near Newport

Vacation Home in 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.
$398 nightly
The price is $451
Dec 16 - Dec 17
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport
Beach nearby, beach towels
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Vacation Home in Westport

9.8 out of 10, Exceptional, (22)
"Beautiful house! Had a wonderful time!"
United States
RYAN S.
$400 nightly
The price is $439
Dec 1 - Dec 2
Total with taxes and fees
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
2 bedrooms, desk, iron/ironing board, free WiFi
Middletown Modern Apartment - RIBryan Property

Apartment in Middletown

9.6 out of 10, Exceptional, (16)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
$356 nightly
The price is $384
Nov 30 - Dec 1
Total with taxes and fees
Middletown Modern Apartment - RIBryan Property
TV
Between Beaches

Vacation Home in Easton's Point

8.0 out of 10, Very Good, (1)
$590 nightly
The price is $668
Dec 1 - Dec 2
Total with taxes and fees
Between Beaches
Exterior
Beach house walking distance to Second Beach

Vacation Home in 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.
$546 nightly
The price is $590
Nov 30 - Dec 1
Total with taxes and fees
Beach house walking distance to Second Beach
Fridge, microwave, oven, stovetop
Little Creek Retreat - RIBryan Property

Vacation Home in Middletown

9.4 out of 10, Exceptional, (14)
"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 $667
Nov 29 - Nov 30
Total with taxes and fees
Little Creek Retreat - RIBryan Property
TV
Ellery Beach Bungalow #45- A Refined Island Escape

Vacation Home in Middletown

10.0 out of 10, Exceptional, (1)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
$382 nightly
The price is $433
Nov 30 - Dec 1
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape
Fridge, microwave, oven, stovetop
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Vacation Home in 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
Dec 22 - Dec 23
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Vacation Home in 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
Nov 29 - Nov 30
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Outdoor dining
Remodeled Seaside Village Retreat, 5-minute walk to village center

Vacation Home in Dartmouth

10.0 out of 10, Exceptional, (13)
"Our family returned this year for a week and enjoyed it even more than last year, which was very hard to top!"
United States
Wilson P.
$1,471 nightly
The price is $1,643
Nov 29 - Nov 30
Total with taxes and fees
Remodeled Seaside Village Retreat, 5-minute walk to village center
Exterior
Middletown Bungalow - RIBryan Property

Vacation Home in Middletown

9.4 out of 10, Exceptional, (13)
"Very clean and roomy for our 8 guests. Perfect location for access to Second Beach and downtown Newport."
United States
William H.
$530 nightly
The price is $572
Nov 30 - Dec 1
Total with taxes and fees
Middletown Bungalow - RIBryan Property
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

Fairfield Inn & Suites by Marriott New Bedford

Fairfield Inn & Suites by Marriott New Bedford

10/10 Excellent
"very kind staff, close to where i needed to be, great breakfast "
Kayla 1-night trip
Posted 4 days ago
Fairfield Inn & Suites by Marriott New Bedford

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 $188 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.

Explore a world of travel with Expedia

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 Gooseberry Island 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.