Vacation rentals in Cuttyhunk Island

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Top-rated vacation rentals in Cuttyhunk Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 Steps to Beach with Water Views

This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a cape style cottage community that offers a private association beach. There are water views from both the living room and deck. Grab the provided beach chairs, water tubes, cooler and walk a 140 steps from the deck to the beach. You can also walk, bike, or fish on cape cod canal nearby. Close to restaurants, hiking trails and Golf Courses. Cape Cod Bridge 2 min away. Early Bird deals in May/Sept.

Dec 28 – Jan 4

G$27,929 GYD per night
Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 266 reviews

Country Charm yet minutes to Newport

This apartment is located in the southeast sector of Middletown and is less than a mile from Newport. The area is close to the beaches of Aquidneck Island, the fabulous Cliff Walk and is three miles from Naval Station Newport. The property is well kept and offers off street parking. There is also a small deck with awning which offers a scenic and private place to relax. Two night minimum! Apartment is attached to a two hundred year old farmhouse. Note to military: 25% discount for extended stay

Nov 6 – 13

G$30,466 GYD per night
Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 301 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Feb 4 – 11

G$21,584 GYD per night

Popular amenities for Cuttyhunk Island vacation rentals

Other great vacation rentals in Cuttyhunk Island

Guest favorite

Tiny home in Smithfield

4.97 out of 5 average rating, 585 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Sep 2 – 9

G$30,683 GYD per night
Guest favorite

Apartment in Portsmouth

4.92 out of 5 average rating, 141 reviews

ALL NEW! Private 1 Bed Apartment w/ Water Views

Feb 14 – 21

G$23,888 GYD per night
Guest favorite

Loft in Westport

4.88 out of 5 average rating, 238 reviews

Brithaven Farm

Dec 24 – 31

G$37,941 GYD per night
Guest favorite

Apartment in Newport

4.95 out of 5 average rating, 264 reviews

"ROOM AT BOB'S'

Dec 23 – 30

G$31,575 GYD per night
Guest favorite

Apartment in Fairhaven

4.97 out of 5 average rating, 208 reviews

Historic Fairhaven Village Garden-Level Suite

Nov 19 – 26

G$23,979 GYD per night
Guest favorite

Place to stay in Falmouth

4.94 out of 5 average rating, 297 reviews

Cottage facing fresh water pond

Dec 15 – 22

G$30,263 GYD per night
Guest favorite

Guest suite in Narragansett

4.89 out of 5 average rating, 399 reviews

Private Suite

Apr 2 – 9

G$21,983 GYD per night
Guest favorite

Guest suite in South Kingstown

4.94 out of 5 average rating, 116 reviews

Guest suite on private lake

Aug 23 – 30

G$30,388 GYD per night
Guest favorite

Apartment in Newport

4.98 out of 5 average rating, 218 reviews

Broadway Studio

Mar 11 – 18

G$21,822 GYD per night
Guest favorite

Cottage in Plymouth

4.96 out of 5 average rating, 160 reviews

Stunning ocean views, stairs down to the beach

Feb 13 – 20

G$100,358 GYD per night
Guest favorite

Cottage in Westport

5.0 out of 5 average rating, 23 reviews

Little Miss Sunshine: cozy New England cottage

Jan 11 – 18

G$31,518 GYD per night
Guest favorite

Cottage in Fairhaven

4.95 out of 5 average rating, 84 reviews

Seaside cottage

May 4 – 11

G$20,852 GYD per night

Destinations to explore

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  3. Massachusetts
  4. Dukes County
  5. Gosnold
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