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Our top choices for Cuttyhunk holiday rentals

Walk to the Beach - Serene Coastal Country Cottage

Walk to the Beach - Serene Coastal Country Cottage
Middletown
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely perfect spot and home. Close enough to everything one wants to be close to while being outside of the hustle and bustle. Beautiful outside dining was perfect for morning coffee while kiddo played in the yard. The third bedroom was also the tv room, which meant negotiating shared space, but it all worked out. We would love to stay here again."
United States
Anne R.
The price is £1,061
includes taxes & fees
3 Jun - 4 Jun
Walk to the Beach - Serene Coastal Country Cottage

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.4 out of 10, Exceptional, (16 reviews)
"Wonderful house and great location!! Super responsive host. Great vacation, thank you!!! "
United States
Kristen P.
The price is £538
includes taxes & fees
1 Jun - 2 Jun
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

WALK to BEACH/CLIFF WALK! FANTASTIC Location! Winter Rentals! Fenced yard! Pets!

WALK to BEACH/CLIFF WALK! FANTASTIC Location! Winter Rentals! Fenced yard! Pets!
Middletown
10.0 out of 10, Exceptional, (51 reviews)
"Great location, very close to all things in Newport!"
United States
Corrine M.
The price is £630
includes taxes & fees
1 Jun - 2 Jun
WALK to BEACH/CLIFF WALK! FANTASTIC Location! Winter Rentals! Fenced yard! Pets!

Little Creek Retreat Private hot tub & yard - RIBryan Properties

Little Creek Retreat Private hot tub & yard - RIBryan Properties
Middletown
9.4 out of 10, Exceptional, (15 reviews)
"Best stay "
United States
Justin R.
The price is £496
includes taxes & fees
31 May - 1 Jun
Little Creek Retreat Private hot tub & yard - RIBryan Properties

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Westport
9.8 out of 10, Exceptional, (44 reviews)
"House is perfect for a family! Great location, beautiful views and nice and clean. Lots of room and great deck for sunset viewing. "
United States
Stacy G.
The price is £286
includes taxes & fees
9 Jun - 10 Jun
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
The price is £698
includes taxes & fees
31 May - 1 Jun
4-bedroom house in lovely Edgartown..Centrally located

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (11 reviews)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is £385
includes taxes & fees
1 Jun - 2 Jun
Charming cottage overlooking the bay in Padanaram Village.

Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is £611
includes taxes & fees
30 May - 31 May
Lovely two bedroom apartment with indoor fireplace

Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (16 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is £464
includes taxes & fees
22 Jun - 23 Jun
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

beach time awaits you at Ocean View

beach time awaits you at Ocean View
Middletown
10.0 out of 10, Exceptional, (21 reviews)
"Place was super cute and had everything we needed. Was centrally located to everything we wanted to do. Beds and comfortable and lots of space to spread out. Would definitely recommend to others. "
United States
Judith G.
The price is £900
includes taxes & fees
31 May - 1 Jun
beach time awaits you at Ocean View

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (40 reviews)
"We really liked the area - quiet - spacious apartment Nice attention to details . Had a full kitchen with dishes etc. one suggestion is for host to provide a muffin pan."
United States
stephen
The price is £167
includes taxes & fees
31 May - 1 Jun
The Charming Gem Near The Water!

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
The price is £2,360
includes taxes & fees
10 Jun - 11 Jun
Beautiful Estate with salt water pool & pond with kayaks

Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties

Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties
Middletown
8.8 out of 10, Excellent, (6 reviews)
"The host always responded to dQuestions before and during stay. Great accommodations, comfy beds, well stocked. Would be great in the warmer weather as backyard has a nice setup. "
United States
Susan C.
The price is £759
includes taxes & fees
12 Jun - 13 Jun
Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties

Seapowet suite

Seapowet suite
Tiverton
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful area Wonderful accommodationsPlenty of space and welcoming host! "
United States
Dena E.
The price is £193
includes taxes & fees
1 Jun - 2 Jun
Seapowet suite

Ellery Beach Bungalows – Five Stays, One Retreat

Ellery Beach Bungalows – Five Stays, One Retreat
Middletown
10.0 out of 10, Exceptional, (1 review)
Ellery Beach Bungalows – Five Stays, One Retreat

Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
6.8 out of 10, (3 reviews)
"Stay was great! "
United States
Zoe D.
The price is £242
includes taxes & fees
30 May - 31 May
Lovely 4- Bedroom apartment for rent

4-bedroom house in Tisbury for a relaxing getaway - newly renovated

4-bedroom house in Tisbury for a relaxing getaway - newly renovated
Tisbury
4-bedroom house in Tisbury for a relaxing getaway - newly renovated

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (216 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
The price is £552
includes taxes & fees
10 Jun - 11 Jun
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Third Beach Road

Third Beach Road
Middletown
6.0 out of 10, (1 review)
"Renovated house, very cute. Kitchen was definitely a highlight as it was a good space for cooking and gathering together. Some amenities of house were not exactly as listed in description. Location of house was nice-close to beach and park with pickleball courts, easy access to Newport wharves and restaurants "
United States
Janet S.
Third Beach Road
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 £360 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. 

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?

Private cottage nestled in center of the Vineyard: This holiday home rental outside of Cuttyhunk is located in a rural location, and has a garden, a selection of games 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.