Holiday Rentals in Cuttyhunk

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Holiday Rentals in Cuttyhunk

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
9.0 out of 10, Wonderful, (35)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
United States
Maryann B.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Cozy getaway in a central location w/ a full kitchen & furnished deck
6.6 out of 10, (24)
"The home was nice, a little outdated, but great for a family. Unfortunately it does not have AC and when we arrived we found 2 fans were broken. We immediately contacted Vacasa who said they would send maintenance. While waiting for maintenance, we also noticed within the first hour that one of the dining chair backs was broken/not attached, one of the bed posts fell off as it was not attached, and the fan in one of the bathrooms was stuck on. We planned to notify maintenance when they came but...
United States
Dawn R.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.4 out of 10, (31)
"It is an old home that has had no updates. It’s shabby- a little bit of a smell and outdated furniture. That being said, it has everything you need and is a good location on the island, especially if you are driving. It was a deal compared to everything else around and was somehow available during summer with less than 2 months before we booked."
United States
Myrtle A.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Beachside Village Resort
3.0 star property
9.2 out of 10, Wonderful, (100)
"Wonderful location, nice staff!"
United States
Claire
Beachside Village Resort
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
10.0 out of 10, Exceptional, (107)
"The property was amazing and the host was so easy to communicate with! We love to the location and would definitely stay again"
United States
Kayla Z.
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
Stones Throw Waterfront
8.8 out of 10, Excellent, (6)
"According to the listing, the property has AC. That is not true. It had a tiny portable unit that wasn't on when we entered and didn't cool once it was turned on. It also had a window unit that had no place to plug in. There were bugs in multiple areas. The property was not habitable, so we ended up booking a hotel room in a nearby town. VRBO compensated us partially but the owner was unwilling to refund any of our money even though we did not stay in the property. "
United States
Ashley R.
The price is €576
includes taxes & fees
7 Nov - 8 Nov
Stones Throw Waterfront
Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
10.0 out of 10, Exceptional, (10)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
United States
christine l.
The price is €334
includes taxes & fees
10 Nov - 11 Nov
Charming cottage overlooking the bay in Padanaram Village.
Charming newly renovated home in Little Compton.
10.0 out of 10, Exceptional, (6)
"This house is an absolute gem – a perfect blend of old New England charm but completely newly renovated. Pamela has thought of everything that a guest could need to make your stay comfortable and relaxed. The house is sparkling clean with spacious bedrooms, beautiful bathrooms, a fully stocked kitchen and lots of room for a family to spread out and enjoy your time in the lovely town of Little Compton. We also appreciated that it is equidistant to points in Westport and Tiverton, which made for...
United States
Sarah C.
Charming newly renovated home in Little Compton.
Seapowet suite
9.6 out of 10, Exceptional, (4)
"Really enjoyed the accommodations / bright and spacious with cathedral ceilings, and lots of light - beautiful natural setting - secluded but also conveniently located. Host was friendly and responsive. Would definitely recommend."
United States
Tom C.
The price is €169
includes taxes & fees
9 Nov - 10 Nov
Seapowet suite
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
2.0 star property
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
United States
Matthew
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is €1,082
includes taxes & fees
7 Nov - 8 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View
10.0 out of 10, Exceptional, (169)
"Fantastic beach house. Thoughtfully stocked with everything you may need. Great location and convenient to all beaches and Newport. We highly recommend a stay at this beautiful spot."
United States
Sally C.
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View
Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master
10.0 out of 10, Exceptional, (126)
"Great beach house for families!"
United States
Joanne M.
Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master
Cape Cod Cottage Retreat - Close to Beaches, Bike Paths & Downtown Shops!
Cape Cod Cottage Retreat - Close to Beaches, Bike Paths & Downtown Shops!
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
9.8 out of 10, Exceptional, (23)
"Amazing place. Definitely steps from the beach . Also the walk into town was not bad at all. we enjoyed doing that. The house was spacious and clean. Communications were great with the owner Joe. We really enjoyed our stay there. highly recommend the place."
United States
Anonymous traveller
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Private Spacious Pet Friendly Studio / Loft
10.0 out of 10, Exceptional, (79)
"Easy checkin and very comfortable - nice, friendly hoats"
United States
Susan T.
Private Spacious Pet Friendly Studio / Loft
Middletown Bungalow - RIBryan Property
9.4 out of 10, Exceptional, (13)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
The price is €860
includes taxes & fees
6 Dec - 7 Dec
Middletown Bungalow - RIBryan Property
Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island
10.0 out of 10, Exceptional, (185)
"This is the fifth year that I’ve rented this place and I love it. It’s very private simple all on one floor."
United States
Debbie I.
Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island
Spacious home in central location with beautiful patio, pool table, W/D, & AC
10.0 out of 10, Exceptional, (4)
"Absolutely loved our stay at this Oak Bluffs home! The location was perfect—just a 20-minute walk to downtown—and the house itself was warm, inviting, and beautifully laid out with an open-air feel. The kitchen was fully stocked, the beds were super comfortable, and the outdoor shower was a wonderful bonus. We felt completely relaxed and free during our stay. Can’t wait to come back next summer!"
United States
Monica D.
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
9.8 out of 10, Exceptional, (47)
"Fantastic beach cabin in a nice location, close to Gay Head lighthouse and several beaches, including the dog-friendly Lobsterville. Good views, plenty of land, we had a good time!"
United States
Bart S.
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
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.
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Top Cuttyhunk Hotel Reviews

Find out more about Cuttyhunk

Everything you need to know about Cuttyhunk holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cuttyhunk holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cuttyhunk holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cuttyhunk. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cuttyhunk holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk holiday rentals we have selected for you start as low as €169 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cuttyhunk rentals

At Expedia, we put the best Cuttyhunk holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cuttyhunk rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cuttyhunk holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cuttyhunk. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.