A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Cuttyhunk vacation homes

Dining

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

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Dartmouth
The price is AED 481
AED 1,153 total
includes taxes & fees
21 Jul - 22 Jul
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Pool

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, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is AED 863
AED 1,900 total
includes taxes & fees
15 Jul - 16 Jul
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Exterior detail

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 AED 702
AED 2,045 total
includes taxes & fees
6 Jul - 7 Jul
Ellery Beach Bungalow #45- A Refined Island Escape
TV

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (96 reviews)
"This was the perfect size and location for our group of 5, would definitely stay again! "
United States
toni g.
The price is AED 764
AED 2,133 total
includes taxes & fees
21 Jul - 22 Jul
Ellery Bungalow #51- Island Calm Near Newport
Property grounds

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Fantastic stay! "
United States
Cristin C.
The price is AED 613
AED 1,926 total
includes taxes & fees
29 Jul - 30 Jul
Ellery Beach Bungalow #47- Relaxed Island Living
Terrace/patio

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Westport
9.6 out of 10, Exceptional, (45 reviews)
"Super quiet and private neighborhood which makes for great walks!"
United States
Caitlin J.
The price is AED 1,107
AED 1,413 total
includes taxes & fees
5 Jul - 6 Jul
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Interior

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (29 reviews)
"Great house and communication with the owner! We would stay there again!"
United States
Stan C.
The price is AED 988
AED 2,718 total
includes taxes & fees
12 Jul - 13 Jul
Beach house walking distance to Second Beach
TV, computer monitors

Pop, Bubble, and sun-drenched Cutie Cottage!

Pop, Bubble, and sun-drenched Cutie Cottage!
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We loved our stay! The cottage was the perfect size for what we needed and a great location! We would definitely stay again."
United States
Lauren C.
The price is AED 879
AED 1,778 total
includes taxes & fees
19 Jul - 20 Jul
Pop, Bubble, and sun-drenched Cutie Cottage!
Exterior

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is AED 1,554
AED 3,438 total
includes taxes & fees
13 Jul - 14 Jul
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
Interior

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, (218 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

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

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.4 out of 10, Exceptional, (16 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.
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
TV

Stepping Stone

Stepping Stone
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"This vacation place was clean, beautiful and comfortable with easy access to downturn Newport, the beaches and all the area has to offer. Perfect stay for our family wedding weekend."
United States
George
The price is AED 1,098
AED 3,287 total
includes taxes & fees
1 Jul - 2 Jul
Stepping Stone
Dining

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (1 review)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
The price is AED 2,571
AED 5,555 total
includes taxes & fees
26 Jul - 27 Jul
4-bedroom house in lovely Edgartown..Centrally located
TV, fireplace, books

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.2 out of 10, Wonderful, (5 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 AED 2,755
AED 5,149 total
includes taxes & fees
30 Jul - 31 Jul
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Fridge, microwave, oven, stovetop

Little Creek Retreat Private hot tub & yard - RIBryan Properties

Little Creek Retreat Private hot tub & yard - RIBryan Properties
Middletown
9.4 out of 10, Exceptional, (15 reviews)
"Best stay "
United States
Justin R.
The price is AED 2,775
AED 4,781 total
includes taxes & fees
21 Jul - 22 Jul
Little Creek Retreat Private hot tub & yard - RIBryan Properties
Sauna

4br & 2ba Ranch style house w/ huge backyard!

4br & 2ba Ranch style house w/ huge backyard!
PORTSMOUTH
10.0 out of 10, Exceptional, (7 reviews)
"Clean, well stocked, quiet place to stay. It was friendly to both people and pets. Near Newport attractions but not in the hustle and bustle. Great place to stay for all."
United States
Martha D.
The price is AED 2,479
AED 4,187 total
includes taxes & fees
20 Jul - 21 Jul
4br & 2ba Ranch style house w/ huge backyard!
Interior

Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill

Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill
Falmouth
The price is AED 3,306
AED 6,722 total
includes taxes & fees
30 Jul - 31 Jul
Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"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.
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (1 review)
"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 AED 610
AED 1,918 total
includes taxes & fees
29 Jul - 30 Jul
Ellery Bungalow #49 - Minutes from the Sand
Private kitchen

Charming Vineyard Classic Home, Walk to Town & Boat

Charming Vineyard Classic Home, Walk to Town & Boat
Vineyard Haven
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay thank you "
United States
Joseph S.
Charming Vineyard Classic Home, Walk to Town & Boat
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

8/10 Good
"We had a wonderful stay at the Vineyard Harbor hotel! It's a great location and the staff was friendly and helpful. Spencer even helped us carry our bags up the stairs! The rooms are cozy and clean, but with some wear and tear. Sitting by the beach (night and day) the proximity to town and transport during the day more than make up for some of the "rough spaces" and the friendly staff was wonderful. Highly recommend unless you are looking for more luxury and something brand new."
Suzanne 2-night trip
Posted 17 hours ago
Vineyard Harbor Motel - Private Beach

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