Cuttyhunk Holiday Rentals

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Holiday Rentals in Cuttyhunk

Apartment in Falmouth

3.0 star property
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort

Holiday Home in Oak Bluffs

6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Apartment in Middletown

9.8 out of 10, Exceptional, (164)
"Great location and easy to check-in and check-out."
United States
Geoffrey H.
Newport - Exclusive Renfrew Park Beach House Waterview Apartment, Central A/C

Holiday Home in Tisbury

10.0 out of 10, Exceptional, (67)
"The house was well stocked and had everything you could need. "
United States
ROBYN M.
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

Cottage in Tiverton

10.0 out of 10, Exceptional, (187)
"Great place, quaint, clean, and hosts are super sweet. "
United States
Todd H.
Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island

Holiday Home in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is AU$1,805
includes taxes & fees
4 Dec - 5 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Holiday Home in Easton's Point

10.0 out of 10, Exceptional, (170)
"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

Holiday Home in Middletown

10.0 out of 10, Exceptional, (126)
"Great location, lots of room, well appointed kitchen and plenty of room for seating, dining, etc. great views from roof deck. thoughtful hosts! Would stay again."
United States
Jodi E.
Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master

Cottage in Tisbury

10.0 out of 10, Exceptional, (31)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
United States
Dave B.
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Holiday Home in Easton's Point

9.8 out of 10, Exceptional, (148)
"What a beautiful property in a fantastic location! Laura was first rate communicating with us. Such a great experience-thank you!"
United States
Amy H.
DISCOUNTS for FALL/WINTER! Ocean views, Walk to Beach, Central AC, 4 Car Parking

Holiday Home in Middletown

9.4 out of 10, Exceptional, (13)
"Very clean and roomy for our 8 guests. Perfect location for access to Second Beach and downtown Newport."
United States
William H.
The price is AU$970
includes taxes & fees
17 Dec - 18 Dec
Middletown Bungalow - RIBryan Property

Holiday Home in Edgartown

10.0 out of 10, Exceptional, (3)
"Beautiful house in Edgartown, was a perfect stay!"
United States
Alec G.
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

Holiday Home in West Tisbury

10.0 out of 10, Exceptional, (35)
"Our very favorite place on the Vineyard!! "
United States
Jean C.
Sanctuary House: An ocean-view farmhouse retreat

Holiday Home in Aquinnah

5.8 out of 10, (7)
"A short walk and you will be in Lobsterville beach, which to me is a beautiful island. If you are a fishing person a short drive and you go to fishing spots on this aprt of the island. Also driving distance is the Chullmark Store has very good products if you need somethign quick. And Menemsha ( fishing port) is about 15 to 20 minues away! I could not ask for any better location. The house is rustic , the location is pristine so make sure you bring impprtant items hat you think you may need."
United States
Betsy A.
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

Holiday Home in Falmouth

9.8 out of 10, Exceptional, (23)
"Great stay. Everything worked perfectly and very close to the beach."
United States
Peter J.
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

Holiday Home in Falmouth

7.6 out of 10, Good, (10)
"Property was as desirables Location was quite but assessable to the village with ease Recommended highly"
United States
Timothy K.
5BD Tranquil Falmouth Breeze Escape w/ Pool

Holiday Home in Falmouth

10.0 out of 10, Exceptional, (16)
"Great place, loved it! "
United States
stephen c.
Gorgeous Spacious Victorian Cape Cod Beach View Retreat

Holiday Home in Easton's Point

10.0 out of 10, Exceptional, (33)
"Great location , convenient to downtown Newport and beach front property. Very responsive owner."
United States
Saraellen S.
Beach Haven by STAY Newport

Apartment in Little Compton

10.0 out of 10, Exceptional, (79)
"It was a gem of a place - artfully decorated, compact, lovely!"
United States
Catherine Dun R.
Private Spacious Pet Friendly Studio / Loft

Holiday Home in Edgartown

5.0 out of 10, (2)
"Our stay was actually not a stay! As per usual when we stay at a rental, we do a walk through before bringing our belongings inside. Upon entering, we were immediately hit with odors of mold and mildew. The air in one of the upstairs bedrooms was in the 50's when the thermostat said it was set to 70. In the other bedroom the air was not working at all. We couldn't stay in the house more than 5 minutes with the smell due to both of us having respiratory issues. We called Vacasa immediately and...
United States
Shonetra W.
Centrally located Island getaway with bike path access, patio, W/D, & games
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, 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 favourite 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 depend 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 AU$970 per night. Entering your travel dates in the search wizard might find you 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. 

Frequently asked questions

Can I find a holiday rental in Cuttyhunk?

Yes, there are holiday rentals close to the most popular sights in Cuttyhunk, or you can select a more secluded option if you're looking for a relaxing stay. Cuttyhunk is known for its beaches.

What are some of the best holiday rentals that Cuttyhunk has to offer?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Cuttyhunk is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Cuttyhunk?

Explore the area and family-friendly sights such as Buttonwood Park Zoo, or get out into nature at a spot like Aquinnah Cliffs. Gay Head Lighthouse and Gooseberry Island are a couple of places you'll find in the wider area.

What’s a holiday rental in Cuttyhunk like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cuttyhunk. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.