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Holiday houses 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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Top Guest favourite
A view of Blue Bill Cove is showcased, featuring calm waters reflecting the blue sky and scattered clouds. Marsh grasses line the shore, with distant structures visible along the waterfront, creating a serene outdoor setting.
Cottage in Portsmouth
4.98 out of 5 average rating, 163 reviews

Waterfront Oasis minutes from Newport w/ hot tub!

Welcome to our charming waterfront Oasis! Located on Blue Bill Cove, our private cottage is steps away from Island Park beach, 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
The exterior of Jolee Cottage features a charming architectural design, with a steeply pitched roof and large windows. Two bicycles are parked on the stone path leading to the entrance, complemented by a small outdoor step and decorative elements, providing a welcoming appearance.
Guesthouse in Jamestown
4.94 out of 5 average rating, 326 reviews

Jolee Cottage, near Newport, Narragansett, Beaches

In walking distance to Jamestown Village. Short drive to Newport (14 min); Wickford (15 min); Narragansett (23 min); Block Island Ferry (38 min); and TFG Airport (30 min). The living room has a gas fireplace, desk, flat screen TV, sofa and bath. A spiral staircase leads you to the upper level which has a queen size bed, vanity, reading chair and armoire. Private deck with ocean views of the Pell Bridge and Newport. Cottage is located on property adjacent to Host Home so privacy limited.

Top Guest favourite
Tiny home in Middletown
4.98 out of 5 average rating, 179 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 serene view of the Westport River at dusk features soft pastel hues reflecting on the water. A wooden dock extends into the calm river, framed by gentle grasses in the foreground. The sky transitions from deep blue to warm oranges and yellows as the sun sets.
Cabin in Westport
4.94 out of 5 average rating, 326 reviews

Koselig Cabin on the Farm Coast of New England!

This cabin is full of comforts, convenience, and love. Just 4 miles from the ocean. It is located under a mile to Buzzards Bay Brewery and Westport Rivers Winery and a 5 minute walk to the quiet little neighborhoods private beach on the East Branch of the Westport River. Koselig embodies feelings of family, friends, warmth, love, coziness, contentment, and comfort. We have a custom area and house guide at the Cabin with everything you need to know to maximize your experience in the area!

Guest favourite
Tent in Little Compton
4.92 out of 5 average rating, 26 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
Cottage in Oak Bluffs
4.91 out of 5 average rating, 140 reviews

East Chop Cottage - walk to lighthouse & beach!

This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

Top Guest favourite
The oceanfront cottage is elevated on stilts with white siding. A flight of stairs leads up to the entrance, while sandy beach and gentle waves are visible below. Lush greenery borders the pathway, creating a serene coastal setting.
Cottage in Fairhaven
4.98 out of 5 average rating, 53 reviews

Cozy & Serene Oceanfront Beach House

Cozy oceanfront cottage with private beach access & stunning views of Buzzards Bay. Sit back, take in the gorgeous ocean view, and catch the tranquil sunset each night. Enjoy a bright open floor plan with two bedrooms & full kitchen and wake up each morning to the sound of waves crashing & birds chirping. The neighborhood is quiet & family-friendly, perfect for long walks & nature watching. Surrounded by conservation land, this property is a hidden gem on Fairhaven’s Sconticut Neck!

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, 116 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 showcases an open sliding door leading to a private deck. A gray wicker chair sits on the deck, facing a gravel beach area with distant ocean waves. Lush greenery surrounds the beach, under a clear blue sky.
Campervan/RV in Westport
4.94 out of 5 average rating, 35 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.

Top Guest favourite
Home in Sandwich
4.99 out of 5 average rating, 153 reviews

Salt Eire | Oceanfront Beach Home

Welcome to Salt Eire. Steps to the beach for your morning walks. The sound of waves lulling you to sleep. A place for family and friends to relax and create memories. Nestled in the dunes of East Sandwich beach sits this oceanfront property (bay side) with stunning 360-degree views of Cape Cod Bay and Scorton Creek. Spend your days sunning and swimming before you return home to this comfortably appointed house. Also check out our new sister property down the road @ApresSeaCapeCod

Top Guest favourite
A handcrafted tree house is set among lush greenery, elevated on wooden stilts. Large windows provide ample natural light, showcasing a cozy porch with outdoor seating. The rustic exterior is complemented by cedar shingles and a distinctive peaked roof, blending seamlessly with the surrounding trees.
Treehouse in Wareham
4.97 out of 5 average rating, 226 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
Home in Oak Bluffs
4.92 out of 5 average rating, 303 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!

Popular amenities for Cuttyhunk Island holiday rentals

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