Vacation rentals in Cuttyhunk Island

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Top-rated vacation rentals in Cuttyhunk Island

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Guest favorite

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

Nov 6 – 13

R2,766 ZAR per night

Guest favorite

Guest suite in Oak Bluffs

4.94 out of 5 average rating, 304 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

Jan 21 – 28

R1,959 ZAR per night

Guest favorite

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.

May 10 – 17

R3,079 ZAR per night

Guest favorite

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!

Dec 17 – 24

R2,946 ZAR per night

Guest favorite

Apartment in Falmouth

4.98 out of 5 average rating, 113 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

Oct 20 – 27

R1,333 ZAR per night

Guest favorite

Tiny home in Smithfield

4.97 out of 5 average rating, 591 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Nov 25 – Dec 2

R2,985 ZAR per night

Guest favorite

Loft in Westport

4.88 out of 5 average rating, 239 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.

Jan 6 – 13

R3,423 ZAR per night

Guest favorite

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 cape style cottage community that offers a private association beach. There are water views from both the living room and deck. Grab the provided beach chairs, water tubes, cooler and walk a 140 steps from the deck to the beach. You can also Walk or Bike on Cape Cod Canal, 5 min. Close to restaurants, hiking trails and Cape Cod Bridge -5 min away. 20% off wk.

Sep 3 – 10

R2,275 ZAR per night

Guest favorite

Guest suite in Falmouth

4.97 out of 5 average rating, 130 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!

Sep 19 – 26

R2,482 ZAR per night

Guest favorite

Guest suite in South Kingstown

4.94 out of 5 average rating, 116 reviews

Guest suite on private lake

Scenic lake-front guest suite and access to 2 kayaks. Lake is ideal for swimming, fishing and paddle boarding. Five minutes to the Amtrak station, thirty to Newport, RI and fifteen to RI's best beaches. If you are interested in touring New England, the location is ideal for day trips to Martha's Vineyard, Boston, and NYC. Property sits in the shadow of URI. The suite sleeps up to 2 comfortably, with a queen-sized bed.

Jun 10 – 17

R2,759 ZAR per night

Guest favorite

Apartment in Westport

4.94 out of 5 average rating, 236 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.

Dec 14 – 21

R1,946 ZAR per night

Guest favorite

Apartment in Little Compton

4.95 out of 5 average rating, 299 reviews

Home by the Sea

Full 1st floor ocean view in quiet neighborhood. One bedroom with full sized bed, one bathroom plus a fold out couch in the living room that can convert into a second bed. There also is an additional outdoor H/C shower, patio and charcoal grill. Washer / dryer, fridge, microwave, toaster, coffee maker and gas fireplace.

Aug 18 – 25

R3,679 ZAR per night