Cuttyhunk Vacation Rentals

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Vacation Rentals in Cuttyhunk

The Charming Gem Near The Water!

New Bedford
9.6 out of 10, Exceptional, (34)
"This was wonderful clean comfortable inviting and relaxing place to stay and would definitelyreturn in the future ."
United States
Elizabeth C.
The price is ¥13,117
¥34,016 total
includes taxes & fees
Nov 17 - Nov 18
The Charming Gem Near The Water!

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (10)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
United States
christine l.
The price is ¥31,068
¥57,496 total
includes taxes & fees
Nov 11 - Nov 12
Charming cottage overlooking the bay in Padanaram Village.

Ellery Beach Bungalow #45- A Refined Island Escape

Middletown
10.0 out of 10, Exceptional, (1)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
The price is ¥15,802
¥66,400 total
includes taxes & fees
Nov 11 - Nov 12
Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #47- Relaxed Island Living

Middletown
10.0 out of 10, Exceptional, (4)
"The property was a perfect size, so clean and comfy, gave us everything we wanted for our stay. Thank you so much!"
United States
Samantha S.
The price is ¥15,802
¥66,400 total
includes taxes & fees
Nov 11 - Nov 12
Ellery Beach Bungalow #47- Relaxed Island Living

Seapowet suite

Tiverton
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
The price is ¥17,260
¥28,915 total
includes taxes & fees
Nov 11 - Nov 12
Seapowet suite

Blue Haven Houseboat

2.0 star property
New Bedford
The price is ¥15,956
¥21,251 total
includes taxes & fees
Nov 13 - Nov 14
Blue Haven Houseboat

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

Dartmouth
The price is ¥18,088
¥46,939 total
includes taxes & fees
Nov 16 - Nov 17
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth
10.0 out of 10, Exceptional, (206)
"The house was even nicer than the pictures. We came in March for a long weekend with some friends and had a really great time. Walking distance to so many fun things- great house for all ages!"
United States
Briget R.
The price is ¥24,854
¥76,030 total
includes taxes & fees
Nov 11 - Nov 12
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Ellery Bungalow #51- Island Calm Near Newport

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.
The price is ¥17,797
¥68,481 total
includes taxes & fees
Dec 9 - Dec 10
Ellery Bungalow #51- Island Calm Near Newport

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport
9.8 out of 10, Exceptional, (22)
"We enjoyed our stay and recommend It. Delightful back yard and patio area and a very pleasant front porch."
United States
Alan M.
The price is ¥21,540
¥64,696 total
includes taxes & fees
Nov 12 - Nov 13
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Middletown Modern Apartment - RIBryan Property

Middletown
9.6 out of 10, Exceptional, (15)
"Apartment was very cealn, fully stocked with everything you need. Nicely decorated. Beds were comfy but small. Location was perfect, very Close to the beaches. Would stay again. "
United States
Lene A.
The price is ¥24,624
¥58,906 total
includes taxes & fees
Nov 11 - Nov 12
Middletown Modern Apartment - RIBryan Property

Beach house walking distance to Second Beach

Easton's Point
9.8 out of 10, Exceptional, (25)
"This house is excellent! Great location, great kitchen, gorgeous backyard! Perfect for a family getaway! "
United States
Alexandra L.
The price is ¥27,478
¥90,486 total
includes taxes & fees
Nov 11 - Nov 12
Beach house walking distance to Second Beach

Ellery Bungalow #49 - Minutes from the Sand

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.
The price is ¥15,802
¥66,400 total
includes taxes & fees
Nov 11 - Nov 12
Ellery Bungalow #49 - Minutes from the Sand

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Tisbury
10.0 out of 10, Exceptional, (16)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
United States
Betel G.
The price is ¥76,710
¥166,401 total
includes taxes & fees
Dec 1 - Dec 2
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Little Creek Retreat - RIBryan Property

Middletown
9.4 out of 10, Exceptional, (14)
"We went for 1 night, a group of seven women. The beds are mostly doubles so one of us had to sleep on the pull-out couch, but it was comfortable. Middletown is quiet and gorgeous and we especially enjoyed the proximity to Newport. We had some small issues but they were resolved. Overall a very nice experience."
United States
Dianna G.
The price is ¥36,936
¥102,357 total
includes taxes & fees
Nov 11 - Nov 12
Little Creek Retreat - RIBryan Property

Middletown Bungalow - RIBryan Property

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.
The price is ¥40,547
¥97,475 total
includes taxes & fees
Nov 18 - Nov 19
Middletown Bungalow - RIBryan Property

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs
9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
United States
Leon R.
The price is ¥53,697
¥137,096 total
includes taxes & fees
Nov 11 - Nov 12
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Drift Loft Houseboat

2.0 star property
New Bedford
The price is ¥21,602
¥27,558 total
includes taxes & fees
Nov 18 - Nov 19
Drift Loft Houseboat

Half mile to beach, Family & Pet Friendly, Newly Renovated Full House

Middletown
10.0 out of 10, Exceptional, (18)
"Bonnie Doon has an excellent location and many amenities."
United States
Christine W.
The price is ¥41,423
¥117,476 total
includes taxes & fees
Nov 20 - Nov 21
Half mile to beach, Family & Pet Friendly, Newly Renovated Full House

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is ¥84,381
¥185,937 total
includes taxes & fees
Nov 11 - Nov 12
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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

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?

Cozy getaway in a central location w/ a full kitchen & furnished deck: This vacation home near Cuttyhunk offers a patio, a garden, and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 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 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.