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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$200 nightly
The price is $223
Sep 29 - Sep 30
Total with taxes and fees
The Charming Gem Near The Water!

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.
$444 nightly
The price is $496
Sep 28 - Sep 29
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.

3. 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.
$514 nightly
The price is $574
Sep 28 - Sep 29
Total with taxes and fees
Cozy efficiency apartment/heated pool
A living room with a television, sofa, and wooden columns.

4. Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.4 out of 10, Exceptional, (13 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveler
Lovely 3 bedroom apartment 3rd floor

5. 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.
$316 nightly
The price is $353
Sep 30 - Oct 1
Total with taxes and fees
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

6. 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
$453 nightly
The price is $516
Oct 22 - Oct 23
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport
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
$449 nightly
The price is $502
Sep 30 - Oct 1
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A modern kitchen with white appliances, a teal dining area, and a fireplace.

8. 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.
$420 nightly
The price is $479
Sep 28 - Sep 29
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand
A patio area with wicker chairs, a small table, and a house with a shingled exterior.

9. 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.
$420 nightly
The price is $479
Sep 28 - Sep 29
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

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

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (20 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
$426 nightly
The price is $462
Oct 4 - Oct 5
Total with taxes and fees
Middletown Modern Apartment w/ Private Deck - RIBryan Properties
A wooden deck with a built-in bench and a small enclosed area with a door.

11. 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.
$457 nightly
The price is $521
Sep 27 - Sep 28
Total with taxes and fees
4br & 2ba Ranch style house w/ huge backyard!
A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
$564 nightly
The price is $630
Sep 28 - Sep 29
Total with taxes and fees
Backyard Retreat / 5 Min > Beach & Main St
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, (13 reviews)
"Beautiful area Wonderful accommodationsPlenty of space and welcoming host! "
United States
Dena E.
$256 nightly
The price is $292
Sep 27 - Sep 28
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
$592 nightly
The price is $675
Oct 25 - Oct 26
Total with taxes and fees
Beach house walking distance to Second Beach
A two-story house with a stone chimney, a red front door, and a porch with white railings.

15. Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay at this lovely home. The hot tub was very fun and huge kitchen table was nice for our family. It was conveniently located and well cleaned before our arrival. We recommend this fun spot in Newport."
United States
Michelle N.
$784 nightly
The price is $849
Oct 20 - Oct 21
Total with taxes and fees
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

16. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (31 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.
$407 nightly
The price is $454
Sep 26 - Sep 27
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

17. 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 12 - Oct 13
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

18. 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.
$563 nightly
The price is $645
Sep 27 - Sep 28
Total with taxes and fees
Charming Guesthouse | Walk to Beach | Downtown
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.

19. 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.
$402 nightly
The price is $459
Sep 30 - Oct 1
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape
A beach with a sandy shore and calm water.

20. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
$794 nightly
The price is $887
Sep 28 - Sep 29
Total with taxes and fees
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
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

Inn on the Square

Inn on the Square

10/10 Excellent
"We enjoyed the outdoor lounge area and indoor pool very much. Clean, comfortable bedding and a small fridge. Across the street from a great coffee shop and walking distance to the center of town perfect."
Anna 2-night trip
Posted 2 hours ago
Inn on the Square

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 $574 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 garden, a barbecue grill, and air-conditioning 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.