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.

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Superhost
Home in Portsmouth
5 out of 5 average rating, 4 reviews

Island Park Beachfront|Ocean Views + Steps to Sand

Welcome to our charming waterfront Beach Cottage! Located directly on Island Park Beach, our private cottage is steps away from dining & local attractions. Stroll down Park Ave to enjoy some ice cream and burgers at Schultzy's or a lobster roll from Flo's Clam Shack (seasonal) while you take in the ocean views. Head to Bristol or Newport, relax at one of the local vineyards and breweries, or enjoy a day on the golf course. Our cottage is also conveniently located near wedding venues & colleges.

Top guest favourite
A charming entrance to a tiny house is bordered by vibrant flowers and greenery. Two blue chairs provide a seating area by the door, complemented by potted plants. The wooden deck appears inviting and well-maintained, enhancing access to the home.
Tiny home in Middletown
4.98 out of 5 average rating, 184 reviews

Cozy coastal tiny house getaway

Situated on Easton's Point, brand new ocean front tiny house looks across to Mansion Row with access to a rocky beach for lounging, swimming, or fishing. The property is close to downtown Newport & ideally located between three beaches. The cozy unit has a queen bed, full bath & kitchenette with coffee maker, fridge, and toaster oven. There is a small deck with ocean views, access to ocean front, outdoor shower and off street parking. We provide beach chairs, a beach umbrella and towels.

Guest favourite
A hammock is suspended between two trees in a serene outdoor setting. Sunlight filters through the leaves, casting dappled shadows on the ground covered in small pebbles. In the background, a wide open field stretches under a partly cloudy sky.
Tent in Little Compton
4.93 out of 5 average rating, 29 reviews

Maurolou Farm

Welcome to our family farm. Our campsite offers seclusion with a beautiful view of Quicksand Pond and the Atlantic Ocean. Unplug in a safari style tent with the privacy of 10 acres of farmland and forest. You are 5 min. from a cafe and a general store. A forty five minute drive to Providence, Newport, and Cape Cod; an hour and a half to Boston. The beach is just around the corner. Little Compton is a beautiful farming/fishing community filled with history and country roads to explore.

Top guest favourite
A charming three-story cottage features a distinct A-frame design with large windows. The entrance is framed by a well-maintained lawn and a stone pathway leading to the front door. Surrounded by trees, the home offers a serene and inviting outdoor setting.
Place to stay in North Kingstown
4.96 out of 5 average rating, 69 reviews

The Fairy House - As Seen on HGTV!

If you're looking for a one-of-a kind stay, look no further! This house was the winner of the HGTV's 2024 "Scariest House in America". What began as one man's life-long passion project, finished with a fairytale ending, undergoing a show stopping renovation from TV-famous designer, Alison Victoria. Surreal, serene, and scenic. Situated on 4 private acres, there is plenty of room to spread out, check out, and relax. You're only minutes away from some of the best Rhode Island has to offer.

Guest favourite
Two colorful kayaks are positioned on a concrete dock, with the calm waters of the bay extending into the distance. The sky above is clear with some soft clouds, reflecting a tranquil outdoor setting.
Cottage in Westport
4.9 out of 5 average rating, 118 reviews

Kayaks and Glimpses of Westport Bay

Stay in a lovely and comfortable cottage with partial views of the bay. The water is just a short walk away past our neighbor with shared access to the water. Enjoy swimming, fishing, or relaxing on the float and soak up the sun. You can also explore the Horseneck Beach, wander the trails, taste the local farms and restaurants, and more. If you want to unwind at the cottage, watch shows on the 65" Samsung Smart TV, fast Wi-Fi, sit on the deck, and flip some burgers on the gas grill.

Top guest favourite
The view captures a spacious outdoor area with a gravel surface, surrounded by lush greenery and coastal vegetation. In the background, the vast ocean is visible beneath a bright sky with scattered clouds. The private deck and fire pit area provide a welcoming space for outdoor gatherings.
Camper van/Motorhome in Westport
4.92 out of 5 average rating, 39 reviews

Beachfront Getaway!

This is a unique stay. Located 100 feet from the beach. Surrounded by a bird sanctuary, multiple beaches, bike paths, and restaurants. Provisions and other fun activities just an 8 minute drive away. Enjoy the summer at your secluded beach oasis and experience waking up to the sound of the waves outside your window. The cottage has all the modern comforts including AC and heat. We have plenty of water, but ask that you please conserve as much as possible for showers and dishwashing.

Guest favourite
The exterior of the modern houseboat features a wooden façade and large windows. A small patio area includes two wooden chairs with white cushions, positioned on a textured surface beside the water. The setting is bright under a clear blue sky.
Houseboat in New Bedford
4.95 out of 5 average rating, 66 reviews

Drift Loft Houseboat

Stay aboard this charming houseboat with rooftop seating and the best harbor views, overlooking the historic New Bedford-Fairhaven Swing Bridge. Minutes to beaches, ferries to Martha’s Vineyard & Nantucket, downtown dining, and the Whaling Museum. Steps from Fathoms (award-winning chowder!). Walkable, convenient, unforgettable waterfront escape. 4 min drive to Seastreak Ferry 3 min drive to commuter rail 🚉 10 min walk to downtown New Bedford 2 min walk to Dunkin’ and liquor store

Top guest favourite
A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.
Treehouse in Wareham
4.97 out of 5 average rating, 230 reviews

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

Guest favourite
The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.
Home in Oak Bluffs
4.93 out of 5 average rating, 307 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Guest favourite
Home in Portsmouth
4.91 out of 5 average rating, 34 reviews

Newport•Jacuzzi•Photo Wall•Outdoor Shower

Bring your girls to Newport’s ultimate getaway house! 🌸 Perfect for bachelorettes, birthdays, & weekends away, this photo-worthy home features a flower wall, glam vanities, private yard, complimentary Prosecco, games, outdoor shower & hot tub! Minutes to beaches, vineyards & downtown. Upgrade your stay with in-home chef dinners, spa days, boat charters, gift bags, & pantry stocking. Sleeps up to 10 in style for the perfect Insta-worthy escape!

Top guest favourite
Home in Mattapoisett
4.97 out of 5 average rating, 29 reviews

Buzzard Bay Beachfront Getaway

Our Buzzard Bay getaway (@buzzbaygetaway) is nestled along nearly 100 feet of your very own private beach, boasting breathtaking ocean views from every corner. This coastal gem provides an idyllic retreat with panoramic views of Brandt Island, West Island, and extending all the way to Falmouth and the Elizabeth Islands. The backyard is perfect for outdoor dining and family fun, complete with a barbecue grill, picnic table, and fire pit.

Top guest favourite
Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.
Flat in Little Compton
4.96 out of 5 average rating, 349 reviews

Home by the Sea free beach pass

Private entrance to the full 1st floor with an ocean view in quiet neighborhood. The apartment features a bedroom with full sized bed, private bathroom, private living room with dining area, gas fireplace, tv and couch. Washer/dryer, refrigerator, microwave, coffee maker, toaster and hot plate included are in the apartment. There also is an additional outdoor H/C shower, private patio and gas grill.

Popular amenities for Cuttyhunk Island holiday rentals

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  2. United States
  3. Massachusetts
  4. Dukes County
  5. Gosnold
  6. Cuttyhunk Island