Cuttyhunk Vacation Rentals

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Our top choices for Cuttyhunk vacation rentals

Seapowet suite

Seapowet suite
Tiverton
9.8 out of 10, Exceptional, (8 reviews)
"Adequate for one night. Host friendly."
United States
Louise
The price is ¥12,376
¥17,632 total
includes taxes & fees
Feb 13 - Feb 14
Seapowet suite

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (34 reviews)
"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.
The price is ¥13,211
¥34,258 total
includes taxes & fees
Feb 15 - Feb 16
The Charming Gem Near The Water!

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic stay! "
United States
Cristin C.
The price is ¥18,696
¥71,208 total
includes taxes & fees
Feb 23 - Feb 24
Ellery Beach Bungalow #47- Relaxed Island Living

Blue Haven Houseboat

Blue Haven Houseboat
New Bedford
The price is ¥20,086
¥25,888 total
includes taxes & fees
Mar 2 - Mar 3
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 review)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is ¥17,923
¥70,098 total
includes taxes & fees
Feb 17 - Feb 18
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 reviews)
"This was the perfect size and location for our group of 5, would definitely stay again! "
United States
toni g.
The price is ¥18,696
¥71,208 total
includes taxes & fees
Mar 9 - Mar 10
Ellery Bungalow #51- Island Calm Near Newport

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (26 reviews)
"The house was clean, had every thing you could possibly need. Great location."
United States
Sarah S.
The price is ¥16,548
¥81,748 total
includes taxes & fees
Feb 16 - Feb 17
Beach house walking distance to Second Beach

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "
United States
ralpjh c.
The price is ¥38,241
¥64,288 total
includes taxes & fees
Feb 15 - Feb 16
Charming cottage overlooking the bay in Padanaram Village.

Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (14 reviews)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
The price is ¥39,182
¥96,717 total
includes taxes & fees
Feb 24 - Feb 25
Middletown Bungalow - RIBryan Property

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, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is ¥25,031
¥75,156 total
includes taxes & fees
Feb 22 - Feb 23
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Between Beaches

Between Beaches
Easton's Point
8.0 out of 10, Very Good, (1 review)
The price is ¥24,876
¥103,863 total
includes taxes & fees
Feb 16 - Feb 17
Between Beaches

Perfect spacious getaway 2nd fl

Perfect spacious getaway 2nd fl
New Bedford
The price is ¥16,996
¥50,914 total
includes taxes & fees
Feb 22 - Feb 23
Perfect spacious getaway 2nd fl

Little Creek Retreat - RIBryan Property

Little Creek Retreat - RIBryan Property
Middletown
9.4 out of 10, Exceptional, (14 reviews)
"Best stay "
United States
Justin R.
The price is ¥39,513
¥106,651 total
includes taxes & fees
Feb 24 - Feb 25
Little Creek Retreat - RIBryan Property

Walk to beach corner lot, 5 bed large yard

Walk to beach corner lot, 5 bed large yard
Middletown
The price is ¥250,306
¥440,387 total
includes taxes & fees
Feb 13 - Feb 14
Walk to beach corner lot, 5 bed large yard

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"perfect for our needs"
United States
Ed V.
The price is ¥45,972
¥102,703 total
includes taxes & fees
Feb 26 - Feb 27
Oak Bluffs - Quiet neighborhood

Allston Greens

Allston Greens
Middletown
10.0 out of 10, Exceptional, (9 reviews)
"Great location and perfect layout of the home for our needs"
United States
Anna P.
The price is ¥54,233
¥149,377 total
includes taxes & fees
Feb 23 - Feb 24
Allston Greens

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 reviews)
"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.
The price is ¥53,634
¥136,935 total
includes taxes & fees
Feb 26 - Feb 27
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is ¥76,620
¥166,206 total
includes taxes & fees
Feb 26 - Feb 27
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Spectacular View from Rooftop Deck | Sleeps 12

Spectacular View from Rooftop Deck | Sleeps 12
Easton's Point
10.0 out of 10, Exceptional, (1 review)
"After finding out we had booked hotel rooms with the wrong hotel there were no rooms available last minute for a group of six. Stay Newport was able to get us in last minute and the lodging was wonderful. Very responsive communication. Great location. Very clean and well taken care of property. We wish we could have stayed for a few more days!"
United States
Devon D.
The price is ¥113,719
¥266,706 total
includes taxes & fees
Feb 16 - Feb 17
Spectacular View from Rooftop Deck | Sleeps 12
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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Find out more about Cuttyhunk

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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?

9-bedroom vacation home near Cape Cod Beaches: This vacation home rental near Cuttyhunk is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 9 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 Demarest Lloyd State Park 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.