Cuttyhunk Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Cuttyhunk

Fridge, microwave, oven, stovetop
The Charming Gem Near The Water!

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.
$198 nightly
The price is $221
Nov 17 - Nov 18
Total with taxes and fees
The Charming Gem Near The Water!
Marina
Charming cottage overlooking the bay in Padanaram Village.

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.
$336 nightly
The price is $375
Nov 17 - Nov 18
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
Fridge, microwave, oven, stovetop
Ellery Bungalow #49 - Minutes from the Sand

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.
$382 nightly
The price is $433
Nov 17 - Nov 18
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand
Exterior
Seapowet suite

Seapowet suite

Tiverton
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
$175 nightly
The price is $188
Nov 17 - Nov 18
Total with taxes and fees
Seapowet suite
Interior
Ellery Beach Bungalow #47- Relaxed Island Living

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.
$390 nightly
The price is $442
Dec 9 - Dec 10
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living
Interior
Ellery Bungalow #51- Island Calm Near Newport

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.
$390 nightly
The price is $442
Dec 9 - Dec 10
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport
TV
Blue Haven Houseboat

Blue Haven Houseboat

2.0 star property
New Bedford
$124 nightly
The price is $139
Nov 19 - Nov 20
Total with taxes and fees
Blue Haven Houseboat
Fridge, microwave, oven, stovetop
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

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

Dartmouth
$274 nightly
The price is $306
Nov 19 - Nov 20
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Beach nearby, beach towels
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

☼ 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.
$377 nightly
The price is $414
Nov 17 - Nov 18
Total with taxes and fees
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
Fridge, microwave, oven, stovetop
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, (207)
"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.
$433 nightly
The price is $496
Nov 16 - Nov 17
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
2 bedrooms, desk, iron/ironing board, free WiFi
Middletown Modern Apartment - RIBryan Property

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.
$356 nightly
The price is $384
Nov 16 - Nov 17
Total with taxes and fees
Middletown Modern Apartment - RIBryan Property
Exterior
Beach house walking distance to Second Beach

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.
$546 nightly
The price is $590
Nov 19 - Nov 20
Total with taxes and fees
Beach house walking distance to Second Beach
Fridge, microwave, oven, stovetop
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)
"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.
$971 nightly
The price is $1,085
Dec 1 - Dec 2
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Fridge, microwave, oven, stovetop
Little Creek Retreat - RIBryan Property

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.
$618 nightly
The price is $667
Nov 16 - Nov 17
Total with taxes and fees
Little Creek Retreat - RIBryan Property
4 bedrooms, desk, iron/ironing board, travel crib
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Dartmouth
10.0 out of 10, Exceptional, (13)
"Extremely well designed extremely comfortable and well appointed. Beautiful scenery, and very relaxing."
United States
David J.
$1,221 nightly
The price is $1,364
Nov 26 - Nov 27
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
TV, fireplace
Ellery Beach Bungalow #45- A Refined Island Escape

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.
$382 nightly
The price is $433
Nov 17 - Nov 18
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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.
$792 nightly
The price is $885
Nov 16 - Nov 17
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Highchair
Half mile to beach, Family & Pet Friendly, Newly Renovated Full House

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.
$709 nightly
The price is $766
Nov 20 - Nov 21
Total with taxes and fees
Half mile to beach, Family & Pet Friendly, Newly Renovated Full House
Exterior
Middletown Bungalow - RIBryan Property

Middletown Bungalow - RIBryan Property

Middletown
9.4 out of 10, Exceptional, (13)
"Great location. House is renovated and fit our family perfectly. Backyard is fully fenced in and allowed our dog to roam and be safe. Hot tub is a fun plus! "
United States
Claire T.
$530 nightly
The price is $572
Nov 16 - Nov 17
Total with taxes and fees
Middletown Bungalow - RIBryan Property
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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.
$1,085 nightly
The price is $1,212
Nov 16 - Nov 17
Total with taxes and fees
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

Falmouth Inn

Falmouth Inn

10/10 Excellent
"We were greeted warmly and the hotel had everything we needed. Centrally located with a number of walkable attractions and amenities."
Ethan 1-night trip
Posted 3 days ago
Falmouth Inn

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 $188 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 near Cuttyhunk is located in the city center and has a patio, a garden, and a barbecue grill 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.