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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Cuttyhunk vacation rentals

A living room with a beige sofa, a glass coffee table, and a TV on a wooden cabinet.

1. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (46 reviews)
"A lovely apartment, nicely appointed, and conveniently located. One of my nicest stays to date"
United States
Thomas
$196 nightly
The price is $218
Sep 29 - Sep 30
Total with taxes and fees
The Charming Gem Near The Water!
A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

2. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
$518 nightly
The price is $579
Sep 29 - Sep 30
Total with taxes and fees
Backyard Retreat / 5 Min > Beach & Main St
Interior

3. 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.
$437 nightly
The price is $488
Sep 30 - Oct 1
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
A two-story house with a swimming pool, a covered patio, and a fenced backyard.

4. 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.
$507 nightly
The price is $566
Oct 13 - Oct 14
Total with taxes and fees
Cozy efficiency apartment/heated pool
A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

5. 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.
$276 nightly
The price is $308
Oct 22 - Oct 23
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Living area

6. Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
New Bedford
9.8 out of 10, Exceptional, (11 reviews)
"The apartment was very roomy. We had a small issue with the stove and the owners responded immediately! The price was great. Ill be back to new bedford and will stay here again"
United States
cricket d.
$300 nightly
The price is $335
Sep 30 - Oct 1
Total with taxes and fees
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
A water park with a large central pool, multiple slides, and a variety of play structures.

7. 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
$422 nightly
The price is $471
Sep 30 - Oct 1
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
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.

8. 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.
$399 nightly
The price is $455
Sep 29 - Sep 30
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape
A wooden deck with a built-in bench and a small enclosed area with a door.

9. 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.
$435 nightly
The price is $496
Sep 30 - Oct 1
Total with taxes and fees
4br & 2ba Ranch style house w/ huge backyard!
Living area

10. Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (21 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
$406 nightly
The price is $439
Sep 29 - Sep 30
Total with taxes and fees
Middletown Modern Apartment w/ Private Deck - RIBryan Properties
A patio area with wicker chairs, a small table, and a house with a shingled exterior.

11. Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
8.6 out of 10, Excellent, (7 reviews)
"Fantastic stay! "
United States
Cristin C.
$399 nightly
The price is $455
Sep 29 - Sep 30
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living
A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

12. 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
$399 nightly
The price is $455
Oct 5 - Oct 6
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport
A red wooden house with a front porch, steps leading to the door, and a garden with various plants and flowers.

13. 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.
$240 nightly
The price is $274
Oct 4 - Oct 5
Total with taxes and fees
Seapowet suite
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

14. 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
$537 nightly
The price is $612
Oct 25 - Oct 26
Total with taxes and fees
Beach house walking distance to Second Beach
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

15. 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.
$443 nightly
The price is $495
Oct 12 - Oct 13
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Private kitchen

16. Little Creek Retreat Private hot tub & yard - RIBryan Properties

Little Creek Retreat Private hot tub & yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (18 reviews)
"Best stay "
United States
Justin R.
$618 nightly
The price is $669
Sep 30 - Oct 1
Total with taxes and fees
Little Creek Retreat Private hot tub & yard - RIBryan Properties
A modern kitchen with white appliances, a teal dining area, and a fireplace.

17. Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Very close to the beach. Would highly recommend"
United States
Semo A.
$399 nightly
The price is $455
Sep 29 - Sep 30
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

18. 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.
$711 nightly
The price is $794
Oct 4 - Oct 5
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
Exterior

19. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
$530 nightly
The price is $607
Sep 30 - Oct 1
Total with taxes and fees
Charming Guesthouse | Walk to Beach | Downtown
A modern living room with a grey sofa, a wooden coffee table, and a television mounted on the wall.

20. LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
"This was the perfect location for our Cape Cod getaway. It was very central to everything we were doing while down there, very effortless to get to Martha’s Vineyard as well! The location was perfect with a bunch of different restaurants, shops and other stores all in walking distance. We will definitely consider staying here again in the future!"
United States
Zack D.
$639 nightly
The price is $732
Sep 30 - Oct 1
Total with taxes and fees
LUX on Main | Downtown | Parking | Sleeps 6, #201
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

New Bedford Harbor Hotel

New Bedford Harbor Hotel

10/10 Excellent
"I may like take my pillow for next time"
Olga 1-night trip
Posted 19 hours ago
New Bedford Harbor Hotel

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 $566 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.