Cuttyhunk Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Cuttyhunk vacation rentals

Beach nearby, sun loungers, beach towels

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.
$1,250 nightly
The price is $1,425
Jun 3 - Jun 4
Total with taxes and fees
Walk to the Beach - Serene Coastal Country Cottage
Exterior

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.
$614 nightly
The price is $667
Jun 1 - Jun 2
Total with taxes and fees
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Interior

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.
$736 nightly
The price is $839
Jun 1 - Jun 2
Total with taxes and fees
WALK to BEACH/CLIFF WALK! FANTASTIC Location! Winter Rentals! Fenced yard! Pets!
Fridge, microwave, oven, stovetop

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.
$632 nightly
The price is $687
Jun 2 - Jun 3
Total with taxes and fees
Little Creek Retreat Private hot tub & yard - RIBryan Properties
Terrace/patio

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.
$345 nightly
The price is $385
Jun 6 - Jun 7
Total with taxes and fees
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Dining

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
$828 nightly
The price is $925
May 31 - Jun 1
Total with taxes and fees
4-bedroom house in lovely Edgartown..Centrally located
Interior

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.
Interior

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.
$463 nightly
The price is $517
Jun 1 - Jun 2
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
Property grounds

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.
Lovely two bedroom apartment with indoor fireplace
Smart TV

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.
$584 nightly
The price is $635
Jun 22 - Jun 23
Total with taxes and fees
Middletown Modern Apartment w/ Private Deck - RIBryan Properties
TV, fireplace

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.
$1,051 nightly
The price is $1,198
May 31 - Jun 1
Total with taxes and fees
beach time awaits you at Ocean View
Smart TV, stereo

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
$197 nightly
The price is $219
Jun 2 - Jun 3
Total with taxes and fees
The Charming Gem Near The Water!
Exterior

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
$2,840 nightly
The price is $3,172
Jun 10 - Jun 11
Total with taxes and fees
Beautiful Estate with salt water pool & pond with kayaks
Marina

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.
$940 nightly
The price is $1,022
Jun 12 - Jun 13
Total with taxes and fees
Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties
Terrace/patio

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.
$223 nightly
The price is $254
Jun 2 - Jun 3
Total with taxes and fees
Seapowet suite
TV, fireplace

Ellery Beach Bungalows – Five Stays, One Retreat

Ellery Beach Bungalows – Five Stays, One Retreat
Middletown
10.0 out of 10, Exceptional, (1 review)
$1,301 nightly
The price is $1,483
Jun 1 - Jun 2
Total with taxes and fees
Ellery Beach Bungalows – Five Stays, One Retreat
Exterior detail

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.
$289 nightly
The price is $323
May 31 - Jun 1
Total with taxes and fees
Lovely 4- Bedroom apartment for rent
Dining

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

4-bedroom house in Tisbury for a relaxing getaway - newly renovated
Tisbury
$1,228 nightly
The price is $1,372
Jun 7 - Jun 8
Total with taxes and fees
4-bedroom house in Tisbury for a relaxing getaway - newly renovated
Interior

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.
$643 nightly
The price is $736
Jun 7 - Jun 8
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Interior

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.
$1,328 nightly
The price is $1,514
May 31 - Jun 1
Total with taxes and fees
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

Inn on the Square

Inn on the Square

8/10 Good
"We arrived at 5:30 pm and our room was still not ready. We were told that they were under new management as of the day we checked in. They were also not able to provide us with a key upon check-in so when we returned from dinner we had to walk all around the building to the front entrance to get into our room (without a key the other entrances were not accessible). We feel that we should not be charged the additional "facilities fee" for the inconveniences."
Jill 1-night trip
Posted less than an hour ago
Inn on the Square

Find out more about Cuttyhunk

Everything you need to know about Cuttyhunk vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cuttyhunk vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cuttyhunk in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $483 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cuttyhunk rentals

At Expedia, we put the best Cuttyhunk vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Cuttyhunk?

Yes, there are vacation rentals near popular attractions in Cuttyhunk, or you can select a more remote option if you want a relaxing place to stay. Cuttyhunk is known for its beaches.

What are some of the best vacation home rentals in Cuttyhunk?

Private cottage nestled in center of the Vineyard: This vacation home rental near Cuttyhunk is located in a rural location and has a garden, a selection of games, and a barbecue grill 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 larger area.

What’s a vacation rental in Cuttyhunk like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Cuttyhunk. Vacation rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.