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

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Our top choices for Cuttyhunk vacation homes

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ¥146,972
¥257,953 total
includes taxes & fees
Aug 2 - Aug 3
Walk to Beach! Oak Bluffs Home & Studio

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 ¥38,164
¥83,990 total
includes taxes & fees
Jul 27 - Jul 28
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Drift Loft Houseboat

Drift Loft Houseboat
New Bedford
10.0 out of 10, Exceptional, (1 review)
The price is ¥40,113
¥50,611 total
includes taxes & fees
Jul 31 - Aug 1
Drift Loft Houseboat

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

4br & 2ba Ranch style house w/ huge backyard!
PORTSMOUTH
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic spot - house was great for visiting with family. Basemen is a great spot for kids to escape. "
United States
Emo C.
The price is ¥109,620
¥185,136 total
includes taxes & fees
Jul 20 - Jul 21
4br & 2ba Ranch style house w/ huge backyard!

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette
Fairhaven
8.4 out of 10, Very Good, (5 reviews)
"The home was beautiful and well equipped. Perfect location in a quiet new england neighborhood. My family enjoyed our stay!"
United States
lea m.
The price is ¥125,048
¥211,333 total
includes taxes & fees
Aug 4 - Aug 5
World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

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

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (17 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.
The price is ¥84,799
¥155,795 total
includes taxes & fees
Jul 20 - Jul 21
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

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 ¥62,524
¥164,605 total
includes taxes & fees
Jul 21 - Jul 22
Stepping Stone

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 ¥68,695
¥150,381 total
includes taxes & fees
Jul 25 - Jul 26
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is ¥102,312
¥234,189 total
includes taxes & fees
Jul 27 - Jul 28
4-bedroom house in lovely Edgartown..Centrally located

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 ¥86,363
¥167,922 total
includes taxes & fees
Jul 22 - Jul 23
Little Creek Retreat Private hot tub & yard - RIBryan Properties

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, (16 reviews)
"This property is amazing. One of the most thoughtful hosts I have ever had with VRBO. First class all the way. Great location. The view is outstanding. Just a wonderful stay, the kitchen is a dream. Just a fantastic find and I cant wait to return to No Egrets Haven. "
United States
Valerie J.
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

WALK to BEACH/CLIFF WALK! FANTASTIC Location! July OPENING! Fenced yard! Pets!

WALK to BEACH/CLIFF WALK! FANTASTIC Location! July OPENING! Fenced yard! Pets!
Middletown
10.0 out of 10, Exceptional, (51 reviews)
"Great location, very close to all things in Newport!"
United States
Corrine M.
The price is ¥55,216
¥124,782 total
includes taxes & fees
Jul 22 - Jul 23
WALK to BEACH/CLIFF WALK! FANTASTIC Location! July OPENING! Fenced yard! Pets!

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 ¥42,874
¥106,795 total
includes taxes & fees
Aug 9 - Aug 10
Ellery Bungalow #51- Island Calm Near Newport

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.
The price is ¥219,240
¥362,620 total
includes taxes & fees
Jul 20 - Jul 21
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is ¥105,761
¥201,895 total
includes taxes & fees
Aug 5 - Aug 6
Elisa's Cottage - Your Family Vacation Destination

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 ¥129,108
¥237,273 total
includes taxes & fees
Aug 17 - Aug 18
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 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 ¥109,620
¥212,421 total
includes taxes & fees
Jul 30 - Jul 31
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

NEW Construction: a Love Letter to Martha's Vineyard

NEW Construction: a Love Letter to Martha's Vineyard
West Tisbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay at this home in West Tisbury. The house was exactly as described - comfortable, clean, well-appointed, and thoughtfully stocked with everything we needed. The location was perfect for exploring the island while still feeling peaceful and relaxing. Jack was incredibly responsive, helpful, and easy to communicate with throughout our stay. We truly felt at home and would gladly stay here again. Highly recommend!"
United States
Nini D.
The price is ¥204,624
¥338,131 total
includes taxes & fees
Aug 3 - Aug 4
NEW Construction: a Love Letter to Martha's Vineyard

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 ¥34,916
¥95,883 total
includes taxes & fees
Aug 10 - Aug 11
Ellery Beach Bungalow #45- A Refined Island Escape

beach time awaits you at Ocean View

beach time awaits you at Ocean View
Middletown
10.0 out of 10, Exceptional, (21 reviews)
"Place was super cute and had everything we needed. Was centrally located to everything we wanted to do. Beds and comfortable and lots of space to spread out. Would definitely recommend to others. "
United States
Judith G.
The price is ¥116,928
¥194,578 total
includes taxes & fees
Jul 26 - Jul 27
beach time awaits you at Ocean View
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

Cuttyhunk Vacation Homes information

Number of reviews
9,687
Accommodation
460 Vacation Homes
Lowest Price
¥19,428
Highest Price
¥106,906

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