A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Cuttyhunk vacation rentals

A two-story house with a swimming pool, a covered patio, and a fenced backyard.

1. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (26 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
$537 nightly
The price is $600
Oct 13 - Oct 14
Total with taxes and fees
Cozy efficiency apartment/heated pool
Interior

2. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
$463 nightly
The price is $517
Oct 11 - Oct 12
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

3. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
$440 nightly
The price is $491
Oct 9 - Oct 10
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
A water park with a large central pool, multiple slides, and a variety of play structures.

4. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
$517 nightly
The price is $577
Oct 31 - Nov 1
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A red wooden house with a front porch, steps leading to the door, and a garden with various plants and flowers.

5. Seapowet suite

Seapowet suite
Tiverton
9.0 out of 10, Wonderful, (15 reviews)
"Beautiful area Wonderful accommodationsPlenty of space and welcoming host! "
United States
Dena E.
$206 nightly
The price is $235
Oct 8 - Oct 9
Total with taxes and fees
Seapowet suite
A wooden deck with a built-in bench and a small enclosed area with a door.

6. 4br & 2ba Ranch style house w/ huge backyard!

4br & 2ba Ranch style house w/ huge backyard!
PORTSMOUTH
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic spot - house was great for visiting with family. Basemen is a great spot for kids to escape. "
United States
Emo C.
$543 nightly
The price is $619
Oct 8 - Oct 9
Total with taxes and fees
4br & 2ba Ranch style house w/ huge backyard!
A single-story house with a grey siding exterior, a front door with a blue doorbell, and a small front yard with a gravel pathway and various plants.

7. 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.
$442 nightly
The price is $504
Oct 12 - Oct 13
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape
A living room with a beige sofa, a glass coffee table, and a TV on a wooden cabinet.

8. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (47 reviews)
"A lovely apartment, nicely appointed, and conveniently located. One of my nicest stays to date"
United States
Thomas
$199 nightly
The price is $222
Oct 18 - Oct 19
Total with taxes and fees
The Charming Gem Near The Water!
A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

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

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Dartmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
$289 nightly
The price is $323
Oct 22 - Oct 23
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

10. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (35 reviews)
"This is a hidden gem, off the beaten path, yet accessible to all the splendors of this beautiful area. The home is spacious and welcoming. The kitchen offers the opportunity to cook all meals comfortably if wanted. The fire pit is a definite bonus."
United States
Kelley
$569 nightly
The price is $649
Oct 25 - Oct 26
Total with taxes and fees
Beach house walking distance to Second Beach
A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

11. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (97 reviews)
"We had a wonderful stay!"
United States
Stacey
$420 nightly
The price is $479
Oct 12 - Oct 13
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport
A spacious living area with a high ceiling, a dining table, and a kitchen area.

12. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
$965 nightly
The price is $1,078
Oct 8 - Oct 9
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

13. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
$469 nightly
The price is $524
Oct 19 - Oct 20
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

14. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,224 nightly
The price is $1,367
Oct 8 - Oct 9
Total with taxes and fees
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

15. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
$753 nightly
The price is $841
Oct 8 - Oct 9
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

16. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
$1,980 nightly
The price is $2,212
Oct 8 - Oct 9
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

17. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (13 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
$561 nightly
The price is $627
Oct 8 - Oct 9
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A two-story building with a covered porch and steps leading to the entrance.

18. Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
6.8 out of 10, (3 reviews)
"Stay was great! "
United States
Zoe D.
$369 nightly
The price is $412
Oct 20 - Oct 21
Total with taxes and fees
Lovely 4- Bedroom apartment for rent
A circular stone patio with Adirondack chairs and a small table in a forested area.

19. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
$640 nightly
The price is $715
Oct 8 - Oct 9
Total with taxes and fees
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A backyard with a seating area, a white fence, and a variety of plants.

20. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
$1,029 nightly
The price is $1,150
Oct 30 - Oct 31
Total with taxes and fees
Delightful 3-bedroom house with AC in Oak Bluffs
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

Best Western Dartmouth-New Bedford

Best Western Dartmouth-New Bedford

10/10 Excellent
"We didn't know what to expect. Never stayed here before. We were very pleased. The lobby was very welcoming. It was very clean, it smelled good. It was all decorated for fall and Halloween really cute. They had our reservation, got us in our rooms. Rooms were lovely, beds were very comfortable. Linens were fresh and clean. Breakfast was tended by a lovely lady who kept everything so tidy and well stocked.. couldn't ask for a nicer stay."
elizabeth 3-night trip
Posted 15 hours ago
Best Western Dartmouth-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 $600 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?

Quaint, ranch style home in Oak Bluffs with central air: This vacation home near Cuttyhunk is located near the beach and has a balcony, a garden, and air-conditioning 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 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.