Vacation rentals in Cuttyhunk Island

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Top-rated vacation rentals in Cuttyhunk Island

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Guest favorite

A vibrant green kayak glides over calm waters, with a person seated inside holding a paddle. In the background, a cottage displays large wall-to-wall windows reflecting the surrounding trees, providing a connection to nature.

Cottage in Sandwich

4.95 out of 5 average rating, 236 reviews

WOW LAKE VIEW! Waterfront, Prvt Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! See a video tour on YouTube: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love the stylish, peaceful, open design; wall-to-wall, floor-to-ceiling windows; private beach with picnic table and chaise lounge chairs; a full, modern kitchen; luxurious King gel/coil bed, private office, bathroom's curved shower, AC, and much more! It's like being on your own luxury houseboat!

Guest favorite

A modern barn house exterior features a dark wood façade with a balcony access. Stone steps lead up to the entrance, flanked by lush greenery and blooming flowers. A pathway of flat stones winds through the vibrant garden, enhancing the serene atmosphere of the property.

Guest suite in West Tisbury

4.94 out of 5 average rating, 155 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.

Top guest favorite

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

4.99 out of 5 average rating, 137 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 favorite

A quaint historic home features classic shingle siding and a welcoming green front door. Windows with evenly spaced panes provide a glimpse of the interior, while a white picket fence and lush greenery frame the property, creating an inviting setting.

Home in Sandwich

5 out of 5 average rating, 211 reviews

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

Top guest favorite

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guesthouse in Chilmark

4.99 out of 5 average rating, 100 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.

Guest favorite

The exterior of the boathouse features a charming wooden door surrounded by shingles and set on a tiled patio. Potted plants are positioned near the entrance. A wooden railing encloses the waterfront view, with calm water and a cloudy sky visible in the background.

Guesthouse in Cranston

4.93 out of 5 average rating, 399 reviews

Waterfront Studio, 10 min to Downtown Providence

Enjoy your own waterfront retreat in this beautifully renovated, professionally cleaned boathouse down a private drive in a quiet, former estate. This hideaway is just 10 minutes to downtown Providence and the colleges and a short, 10-minute picturesque walk to historic Pawtuxet Village for shopping and dining. Enjoy the private deck, full kitchen, king size bed, washer, dryer, and plenty of space for relaxing or working. Note: This space is not suitable for children or infants.

Top guest favorite

A cozy living area features a stone fireplace, with a muted flame providing a warm glow. Above, a flat-screen TV is mounted against white shiplap walls, complemented by exposed beams. A dark wood coffee table sits at the center, surrounded by comfortable seating and decorative accents.

Home in New Bedford

4.99 out of 5 average rating, 246 reviews

Historic Cobblestone Carriage House near Downtown

Enjoy a piece of history at this carriage house! Jonathan Bourne owned a mansion along with this home, and his son purchased a whaler, Lagoda, in 1841. The ship is currently displayed at the New Bedford Whaling Museum, which is walking distance; just four/five blocks of downtown New Bedford, where you can also enjoy shopping, great food, entertainment, and the ferry to either Martha’s Vineyard or Nantucket. New 2025 (MBTA) commuter train rail to Boston and more. Check it out!

Top guest favorite

A quaint cottage is blanketed in snow, with a chimney rising from the sloped roof. Nearby, a bare tree stands, its branches weighed down by frost. The scene conveys a tranquil winter landscape, featuring soft white tones and a serene atmosphere.

Tiny home in Westport

5 out of 5 average rating, 133 reviews

Restored blacksmith shop (cottage) on goat farm

Guest cottage on 300-yr old farmstead, now a working goat farm. Open floor plan with Queen bed, decorative FP, loveseat, ++ seating, bistro table/chairs, WiFi, Roku TV w/ prem. channels, a/c & heat, 3 cu. ft. frig, m'wave, coffee maker/tea kettle. NO KITCHEN facilities. Full bath (w/ shower) in attached ell. Bright & cheery, close to barn & goat pen. Shaded outdoor grass patio w/ teak furniture. Orchard (w/ fire pit), pastures, hay fields, stream, walking trails in woods.

Guest favorite

A charming farmhouse is set against a backdrop of autumn foliage, featuring vibrant trees and a cloudy sky. A garden with various plants and flowers is visible in the foreground, adding natural texture to the scene.

Loft in Westport

4.88 out of 5 average rating, 297 reviews

Brithaven Farm

Brithaven Farm is on 28 acres of fields, woods meadows and gardens. We are just 2 miles from East Beach and the Allen's Pond Wildlife Sanctuary. We are completely private from the road and reached by a long laneway through woods which opens up to fields and meadows The rental has 2 decks, one with a large awning with dining table and chairs to lounge and take in the view. There is an open plan living, dining kitchen area with french doors leading to the deck.

Top guest favorite

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, 210 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 favorite

A charming cottage exterior is presented, featuring shingle siding and a welcoming wraparound deck. Outdoor seating includes a picnic table and several armchairs surrounded by planters with blooming flowers. Large windows provide ample natural light, enhancing the inviting atmosphere of the space.

Home in Little Compton

4.94 out of 5 average rating, 136 reviews

Salt box

Come and Relax! Newly renovated guest cottage in little Compton, Rhode Island on a quiet dead end street. Access to beach, close to town commons, farmers market and Sakonnet and Westport wineries among other special spots. Wonderful walking and biking area. Perfect for couples or a small family to get away. Special note...Memorial Day to Columbus Day house includes a beach pass to Briggs beach. More info will be shared as needed.

Top guest favorite

A serene view of a spacious home set against a backdrop of lush greenery and wildflowers. The house presents an inviting facade with multiple windows, surrounded by the natural beauty of the landscape, creating a sense of tranquility.

Guest suite in North Falmouth

4.99 out of 5 average rating, 198 reviews

The Ideal Spot

The perfect getaway in Falmouth for all seasons! Our home is beautifully located overlooking Bourne’s Farm and we are steps away to the picturesque Shining Sea Bike Path. Enjoy a beautiful scenic 8.5 mile ride winding your way thru the Sippewisset marsh and along the coastline to the seaside village of Woods Hole. Where you can enjoy the local restaurants ,shops and science learning or jump on the ferry to Marta’s Vineyard.