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, 160 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.

Guest favourite
Home in Tisbury
5 out of 5 average rating, 7 reviews

The Lobster Pot: Lake Tashmoo, beachfront

Welcome to The Lobster Pot, your cozy beach cottage on the tranquil shores of Martha's Vineyard. Nestled on the waterfront, this charming retreat is ideal for a paradise getaway. Wake up to the soothing sound of waves, enjoy panoramic ocean views from your private deck, and relax in the gentle sea breeze. With its inviting décor and relaxed ambiance, The Lobster Pot offers a perfect blend of relaxation and adventure. Savor fresh seafood, stroll along the sandy beach, or enjoy stunning sunsets.

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, 325 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.

Guest favourite
Tiny home in Middletown
4.98 out of 5 average rating, 176 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.

Top Guest favourite
Guesthouse in Chlmark
4.99 out of 5 average rating, 109 reviews

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

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, 51 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, 115 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
A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.
Home in Woods Hole
4.93 out of 5 average rating, 128 reviews

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

Guest favourite
The view from a wooden deck showcases a calm lake surrounded by trees displaying autumn foliage. Two pumpkins sit on the railing, complementing the seasonal atmosphere. Reflections of the vibrant leaves create a serene scene across the water.
Bungalow in Dartmouth
4.95 out of 5 average rating, 185 reviews

Updated Vintage Bungalow with Incredible Views

This space has been fully updated in the spring of 2020. Incredible views. It is 400 sq' with an additional 350 sq ' of living space on the deck. The neighborhood is quiet, but you are a stone's 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!

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, 225 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.

Top Guest favourite
Home in Oak Bluffs
4.92 out of 5 average rating, 298 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!

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.
Apartment in Little Compton
4.96 out of 5 average rating, 348 reviews

Home by the Sea

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

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