Cuttyhunk Holiday Rentals

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Holiday Rentals in Cuttyhunk

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
9.8 out of 10, Exceptional, (85)
"The property was clean and quiet. Modem appliances and accents. "
The price is NZ$330
includes taxes & fees
3 Jun - 4 Jun
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
InnSeason Resorts Captain's Quarters
3.5 star property
9.6 out of 10, Exceptional, (145)
"Large, comfortable suite, plenty of amenities"
InnSeason Resorts Captain's Quarters
Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!
10.0 out of 10, Exceptional, (37)
"Super easy check in, sports bar a quick walk away and the beaches a short drive. The cottage was clean and comfy. Would definitely recommend this property."
Ellery Beach Bungalows #51- 1/4 mile walk to beach, - 5 min drive to Newport!
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Private Spacious Pet Friendly Studio / Loft
10.0 out of 10, Exceptional, (47)
"This was a great short stay rental....perfect for two people. The space was lovely and the hosts were available if we needed anything. We would definitely consider a return visit."
Private Spacious Pet Friendly Studio / Loft
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
9.8 out of 10, Exceptional, (65)
"Cute house within walking distance to beach and Main Street. Regina was a wonderful host."
Quiet duplex by the beach, short walk to Falmouth Village, 2GBps Internet.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.0 out of 10, (19)
"There were times when the shower in the master bathroom only emitted cold water. The water spigot in the tubs would not turn completely off in bathroom in the hallway. I had trouble with the lockbox. Maybe add more specific directions. It would have been helpful to know that MV transit bus was available at the intersection of the street and County Road."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Charming and Cozy Beach Cottage
9.6 out of 10, Exceptional, (5)
"This little house was perfect for our wknd away. High ceilings made it feel very spacious and lovely views. Clean and modern. Most comfortable bed ever! Wish we could have stayed longer."
Charming and Cozy Beach Cottage
Escape on conservation land with furnished deck, pond views, sunroom, & AC
8.8 out of 10, Excellent, (9)
"Very nice property. Excellent location!"
Escape on conservation land with furnished deck, pond views, sunroom, & AC
Cottages with easy access to Newport, beaches, nature trails and vineyards
10.0 out of 10, Exceptional, (25)
"Adorable place to stay. Cute layout. Would stay here again. Very comfy bed. Super clean "
The price is NZ$328
includes taxes & fees
2 Jun - 3 Jun
Cottages with easy access to Newport, beaches, nature trails and vineyards
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
8.2 out of 10, Very good, (24)
"Upon entering the property, everything was very clean and welcoming. The rooms were spacious and comfortable. It felt like home. We would definitely book this property again."
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Beautiful bright home with firepit, deck & backyard - walk to beach
9.6 out of 10, Exceptional, (45)
"Very clean, welcoming"
Beautiful bright home with firepit, deck & backyard - walk to beach
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
8.4 out of 10, Very good, (21)
"I thoroughly enjoyed my stay at this property. Easy to find, down a well-maintained dirt road. Check-in was a breeze. Private and quiet. The woods surrounding the property were peaceful and welcome. Deer in the front yard, turkeys in the back, rabbits all around. Super clean and comfy! Weather was spectacular affording many walking opportunities both from and near this rental. Biking would be a plus. Have been renting in April on MV for years...this new location is a prize winner!"
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Renovated 2 Bed Private Home Newport-Middletown Sleeps 6
9.6 out of 10, Exceptional, (25)
"We were in town to watch our sons play rugby for the weekend. The house was perfectly located to where we needed to be. Everything was clean, nicely decorated and comfortable. Matt was very responsive and communicative."
The price is NZ$800
includes taxes & fees
10 Jun - 11 Jun
Renovated 2 Bed Private Home Newport-Middletown Sleeps 6
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
9.6 out of 10, Exceptional, (29)
"This home away from home offers spacious bedrooms and living spaces on a nice grassy lot in a quaint neighborhood setting. Step out onto your deck and sit at the table and watch the little bunnies nibbling the grass and listen to the birds singing. Clean, well-equipped and stocked with essentials, including all linens, this place has got you covered! A bookshelf full of guides and summer reads, toys and games for the kiddos for family time indoors as well as a beach wagon loaded-up for...
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Cozy Massachusetts Escape w/ Patio, Near Beaches!
Heart of Falmouth Main Street Apartment
Heart of Falmouth Main Street Apartment
Luxury home with private pool & foosball - near 3 towns & many beaches
8.6 out of 10, Excellent, (30)
"I recently stayed in this lovely OB home with my family. It was me and 9 other people, and there was plenty of room for everyone. The photos are accurate. The pool was clean and heated. The house is located in a private, wooded area but conveniently located to OB, Edgartown, the airport and beaches. The interior/furniture were so cozy. The house came equipped with enough plates, dishes, pots, pans, utensil, towels, etc. It would be helpful if the house came with a book of instructions, so we'd...
Luxury home with private pool & foosball - near 3 towns & many beaches
Charming salt box in quiet woodsy neighborhood - centrally located!
10.0 out of 10, Exceptional, (7)
"Was perfect for our family!"
Charming salt box in quiet woodsy neighborhood - centrally located!
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
8.4 out of 10, Very good, (18)
"Overall my friends and I have come twice to the Noyes house and are planning to come back next year. As long as you’re comfortable not staying near the main towns, it’s an ideal location - close to the markets and stores of west tisbury, several of the best beaches on the island (Lucy Vincent and Aquinnah in particular), the Chilmark general store, and some of the best farms like beetlebung. The house is something between rustic and luxury, which is deal for a group of friends. It’s not a big...
Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Walk your way into Vineyard Haven from Walker Way!
10.0 out of 10, Exceptional, (33)
"The owner was very nice and friendly and the property was well kept. I would definitely rent again"
Walk your way into Vineyard Haven from Walker Way!
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See all available properties in Cuttyhunk
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Cuttyhunk you may be interested in

Atlantic Beach Hotel Newport
3.5 star property
8.2 out of 10, Very good, (1003)
"Just a short drive away from the Breakers mansion and cliff walk "
The price is NZ$425
includes taxes & fees
4 Jun - 5 Jun
Atlantic Beach Hotel Newport
Wyndham Newport Hotel
4.0 star property
9.2 out of 10, Wonderful, (1103)
"Excellent "
The price is NZ$374
includes taxes & fees
5 Jun - 6 Jun
Wyndham Newport Hotel
Newport Beach Hotel & Suites
3.5 star property
8.0 out of 10, Very good, (1002)
"We booked a 2 night stay following Memorial Day weekend. We found our room to be exactly as described in the online booking description. The room was clean and beautifully decorated. The views of the ocean were gorgeous! We used both the indoor and the rooftop outdoor hot tubs which were well maintained and clean. The staff were very polite and helpful. Thank you for a relaxing, beautiful getaway. We will definitely be back!"
The price is NZ$424
includes taxes & fees
2 Jun - 3 Jun
Newport Beach Hotel & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cuttyhunk holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cuttyhunk. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cuttyhunk. Seeing all the best attractions is bound to make you fall in love with Cuttyhunk. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cuttyhunk short-term rentals, that won’t be hard to do.

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