Holiday houses in Cuttyhunk Island

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Top-rated holiday rentals in Cuttyhunk Island

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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 sought after cape style cottage community. It offers a pristine private association beach. The cottage has water views from both the living room and deck. Grab the provided beach chairs, cooler and walk a 140 steps from the deck to the beach. You can also Walk, Bike, or Fish on Cape Cod Canal, 5 min. Close to restaurants, hiking trails and Mass Maritime. Cape Cod Bridge is 5 min away. 20% off wk.

13 – 20 Apr

$1,761 AUD total

Guest favourite

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

6 – 13 Nov

$1,678 AUD total

Guest favourite

Guest suite in West Tisbury

4.94 out of 5 average rating, 101 reviews

Loft Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the 2nd floor of the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, just off historic Music St, a short walk to a small town center which provides amenities. Ask about our other guest suite if you are with others.

13 – 20 Mar

$1,668 AUD total

Guest favourite

Bungalow in Dartmouth

4.95 out of 5 average rating, 145 reviews

Updated Vintage Bungalow with Incredible Views

This space has been fully updated in the spring of 2020. Incredible unobstructed panoramic views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stones throw from I-195, making places like Boston, Providence and the Cape and Islands very easy to get to. The décor is bright and funky! Close to UMASS. Extensive custom area and house guide is at the Bungalow with everything you need to know to maximize your experience in the area!

8 – 15 Sept

$1,991 AUD total

Guest favourite

Apartment in New Bedford

4.87 out of 5 average rating, 239 reviews

New Bedford Apartment

Easy Living downtown convenience. Walk to bars, restaurants, Martha's Vineyard ferry, bus station steps from location, coffee shops, etc.. Enjoy an area with rich history and lots of character. Inside, the decor is brand new and modern. With plenty of room to spread out. We promise the apartment will be super clean and I will do my best to be the best host for you. We are not far from beaches, the Whaling museum, and shopping. We hope you will consider us for your next stay to the area!

5 – 12 May

$1,098 AUD total

Guest favourite

Apartment in Falmouth

4.98 out of 5 average rating, 116 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

23 – 30 Oct

$971 AUD total

Guest favourite

Guest suite in New Shoreham

4.99 out of 5 average rating, 152 reviews

Hilltop Happiness

We are located high on Mott hill in the center of the island. It's about 2 miles to both harbors. There are lots of hiking trails nearby. We are located near the island airport so small private planes come and go during the day but it is usually very quiet at night. Many of our guests say watching the planes is one of their favorite things. This spot is ideal for visitors who like to retreat to a quieter space at the end of a long day at the beach or an evening on the town.

7 – 14 Oct

$1,998 AUD total

Guest favourite

Guest suite in Newport

4.88 out of 5 average rating, 387 reviews

★2 BEDROOM SUITE★ Wyndham Newport Onshore Resort!

Bundled between the majestic waters of Newport Bay and Historic Thames St. shopping, dining, and drinking, the Newport Onshore Resort will be the ideal New England stay. With Newport as the "Yatching Capital of the World," it is the perfect place to experience all types of boating activities, so once you charter your boat for the day, you can come back and unwind in one of the many pools or sweat it out in the fitness center located on site.

12 – 19 Feb

$1,923 AUD total

Guest favourite

Guest suite in Falmouth

4.97 out of 5 average rating, 131 reviews

Studio in the woods near the beach

Efficient, bright, half-basement studio with large french door entrance looking out on front yard. Includes brand-new queen-size bed, a full bathroom with shower, large closet, lounge space, and well-equipped kitchenette with dining table. Wifi and a ROKU monitor. There is no cable service. Quiet, ideal location in the woods, near shops, restaurant, beach and bike path. Parking space right at the front door. No pets please!

4 – 11 May

$1,292 AUD total

Guest favourite

Apartment in Westport

4.94 out of 5 average rating, 237 reviews

15 Acres of Open Fields & 15 Minutes to the Beach

This is a ground level apartment. It sits in the walkout basement of the main residence. It has 7 east facing windows. Tons of light and faces the 15 acres of field. It was a dairy farm previously so the house is a converted cow barn. It is quiet and serine, far off the road. Enjoy walks in the fields or sit on the swing in the gardens.

31 Oct – 7 Nov

$1,270 AUD total

Guest favourite

Apartment in Fairhaven

4.97 out of 5 average rating, 209 reviews

Historic Fairhaven Village Garden-Level Suite

Garden level suite with private entrance in safe, quiet neighborhood. Completely new renovation with modern amenities, yet classic feel. Located within our family home, a historic structure dating back to the mid 19th century, originally Sawin Hall. Other incarnations of our home include The Second Advent Church and the Fairhaven Grange Hall.

24 – 31 Aug

$1,522 AUD total

Guest favourite

Apartment in New Bedford

4.93 out of 5 average rating, 316 reviews

Exquisite Apartment in New Bedford

Modern apartment right in downtown New Bedford! If you are looking for a place where you can walk to everything you need, then this is your spot. It is a modern, first floor apartment with brand new furniture. If you don't want to walk, no worries, we have off street parking so we will save your spot.

9 – 16 May

$1,110 AUD total