Search Vacation Homes in Cuttyhunk

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Cuttyhunk vacation homes

Vacation Home in 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
Dec 11 - Dec 12
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape

Vacation Home in Middletown

10.0 out of 10, Exceptional, (4)
"Fantastic stay! "
United States
Cristin C.
$382 nightly
The price is $433
Dec 14 - Dec 15
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

Vacation Home in 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.
$382 nightly
The price is $433
Dec 15 - Dec 16
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport

Vacation Home in Falmouth

10.0 out of 10, Exceptional, (210)
"We had a great stay. House is spacious, clean and well-stocked with everything we needed. We loved that we were able to walk to downtown shops and restaurants, the ferry to Martha’s Vineyard and the beach. Would definitely stay here again. "
United States
Ava B.
$433 nightly
The price is $496
Dec 11 - Dec 12
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Vacation Home in New Bedford

2.0 star property
$124 nightly
The price is $139
Dec 16 - Dec 17
Total with taxes and fees
Blue Haven Houseboat

Vacation Home in Easton's Point

9.8 out of 10, Exceptional, (26)
"What a great location, well appointed home, and a very professional VRBO host. You know that love and care goes into making guests feel welcomed and special. Lots of amenities and space to make your stay memorable. "
United States
Victoria L.
$546 nightly
The price is $590
Dec 11 - Dec 12
Total with taxes and fees
Beach house walking distance to Second Beach

Vacation Home in Dartmouth

$278 nightly
The price is $310
Dec 13 - Dec 14
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Vacation Home in Easton's Point

8.0 out of 10, Very Good, (1)
$590 nightly
The price is $668
Dec 13 - Dec 14
Total with taxes and fees
Between Beaches

Vacation Home in 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.
$530 nightly
The price is $572
Dec 14 - Dec 15
Total with taxes and fees
Middletown Bungalow - RIBryan Property

Vacation Home in Middletown

9.4 out of 10, Exceptional, (14)
"Great place! So many bedrooms! Nice private yard, great if you have a dog. Had a wonderful stay, would stay again. Close enough to Newport to drive in and out no problem, plus close to beaches. "
United States
Todd C.
$618 nightly
The price is $667
Dec 14 - Dec 15
Total with taxes and fees
Little Creek Retreat - RIBryan Property

Vacation Home in Tisbury

10.0 out of 10, Exceptional, (16)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
$971 nightly
The price is $1,085
Dec 23 - Dec 24
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Vacation Home in Oak Bluffs

9.4 out of 10, Exceptional, (3)
"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.
$800 nightly
The price is $894
Dec 11 - Dec 12
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Vacation Home in 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.
Ellery Bungalow #49 - Minutes from the Sand

Vacation Home in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
$1,053 nightly
The price is $1,176
Dec 11 - Dec 12
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Vacation Home in Mattapoisett

9.8 out of 10, Exceptional, (7)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
United States
Catherine T.
$1,629 nightly
The price is $1,722
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Vacation Home in Dartmouth

8.8 out of 10, Excellent, (6)
"Perfect spot for our long weekend visiting local family and we wish we could have stayed longer. Close to the village, kayaks on site/ water view- house clean and decorated thoughtfully. Pet friendly, we brought our small dog. The outdoor shower is a must try! We hope to be back soon! "
United States
Lauren G.
$574 nightly
The price is $641
Dec 11 - Dec 12
Total with taxes and fees
Stones Throw Waterfront

Vacation Home in Middletown

10.0 out of 10, Exceptional, (9)
"Great location and perfect layout of the home for our needs"
United States
Anna P.
$848 nightly
The price is $960
Dec 11 - Dec 12
Total with taxes and fees
Allston Greens

Vacation Home in Dartmouth

10.0 out of 10, Exceptional, (13)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
$1,133 nightly
The price is $1,265
Jan 4 - Jan 5, 2026
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Vacation Home in Easton's Point

10.0 out of 10, Exceptional, (1)
"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.
$1,473 nightly
The price is $1,668
Dec 11 - Dec 12
Total with taxes and fees
Spectacular View from Rooftop Deck | Sleeps 12

Vacation Home in Middletown

$2,527 nightly
The price is $2,862
Dec 14 - Dec 15
Total with taxes and fees
Walk to beach corner lot, 5 bed large yard
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cuttyhunk Hotel Reviews

Find out more about Cuttyhunk

Cuttyhunk Vacation Homes information

Number of reviews
392
Accommodation
557 Vacation Homes
Lowest Price
$139
Highest Price
$2,862

Explore a world of travel with Expedia