Holiday rentals in Cuttyhunk Island

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Top-rated holiday rentals in Cuttyhunk Island

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

Guest favourite

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.

24–31 Aug

£128 per night
Guest favourite

Flat 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

6–13 Nov

£124 per night
Guest favourite

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!

8–15 Jan

£109 per night

Popular amenities for Cuttyhunk Island holiday rentals

Other great holiday rentals in Cuttyhunk Island

Superhost

Cottage in Fairhaven

4.79 out of 5 average rating, 277 reviews

On the Beach Cottage in Fairhaven

12–19 Dec

£246 per night
Guest favourite

Loft in Westport

4.88 out of 5 average rating, 238 reviews

Brithaven Farm

23–30 Mar

£161 per night
Guest favourite

Flat in Portsmouth

4.92 out of 5 average rating, 141 reviews

ALL NEW! Private 1 Bed Apartment w/ Water Views

16–23 Dec

£104 per night
Guest favourite

Tiny home in Smithfield

4.97 out of 5 average rating, 585 reviews

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

2–9 May

£129 per night
Guest favourite

Home in Edgartown

4.96 out of 5 average rating, 181 reviews

Brand new gorgeous 2 bedroom guest house.

29 Oct – 5 Nov

£156 per night
Guest favourite

Flat in Fairhaven

4.97 out of 5 average rating, 208 reviews

Historic Fairhaven Village Garden-Level Suite

17–24 Oct

£107 per night
Guest favourite

Flat in Newport

4.95 out of 5 average rating, 264 reviews

"ROOM AT BOB'S'

23–30 Dec

£128 per night
Guest favourite

Flat in Tiverton

4.94 out of 5 average rating, 131 reviews

NEAT, somewhat funky STUDIO APARTMENT - WATERVIEW

3–8 Dec

£104 per night
Guest favourite

Guest suite in South Kingstown

4.94 out of 5 average rating, 116 reviews

Guest suite on private lake

23–30 Aug

£127 per night
Guest favourite

Guest suite in Narragansett

4.89 out of 5 average rating, 399 reviews

Private Suite

2–9 Apr

£89 per night
Guest favourite

Cottage in Westport

5.0 out of 5 average rating, 23 reviews

Little Miss Sunshine: cozy New England cottage

6–13 Jan

£150 per night
Guest favourite

Cottage in Fairhaven

4.95 out of 5 average rating, 84 reviews

Seaside cottage

14–21 Oct

£112 per night

Destinations to explore

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  3. Massachusetts
  4. Dukes County
  5. Gosnold
  6. Cuttyhunk Island