A coastal landscape with a sandy beach, grassy areas, and a small island with a lighthouse.

Cuttyhunk Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cuttyhunk vacation rentals

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
$1,107 nightly
The price is $1,237
Aug 2 - Aug 3
Total with taxes and fees
Walk to Beach! Oak Bluffs Home & Studio

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
New Bedford
9.8 out of 10, Exceptional, (11 reviews)
"We love it here quite neighbors are really nice Angelino is on top of everything great host "
United States
Joann E.
$309 nightly
The price is $345
Jul 29 - Jul 30
Total with taxes and fees
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (45 reviews)
"A lovely apartment, nicely appointed, and conveniently located. One of my nicest stays to date"
United States
Thomas
$199 nightly
The price is $222
Aug 13 - Aug 14
Total with taxes and fees
The Charming Gem Near The Water!

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.
$341 nightly
The price is $381
Jul 29 - Jul 30
Total with taxes and fees
Lovely 4- Bedroom apartment for rent

Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Very close to the beach. Would highly recommend"
United States
Semo A.
$414 nightly
The price is $472
Jul 29 - Jul 30
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (35 reviews)
$463 nightly
The price is $517
Jul 29 - Jul 30
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
$629 nightly
The price is $702
Jul 29 - Jul 30
Total with taxes and fees
Backyard Retreat / 5 Min > Beach & Main St

Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
$429 nightly
The price is $466
Jul 29 - Jul 30
Total with taxes and fees
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
8.6 out of 10, Excellent, (7 reviews)
"Fantastic stay! "
United States
Cristin C.
$442 nightly
The price is $504
Jul 29 - Jul 30
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (15 reviews)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
$502 nightly
The price is $561
Aug 24 - Aug 25
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.

Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (96 reviews)
"This was the perfect size and location for our group of 5, would definitely stay again! "
United States
toni g.
$534 nightly
The price is $608
Aug 26 - Aug 27
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
$457 nightly
The price is $510
Aug 23 - Aug 24
Total with taxes and fees
Small One Bedroom Private Cottage on Large Quiet Property.

Seapowet suite

Seapowet suite
Tiverton
9.2 out of 10, Wonderful, (12 reviews)
"Lovely spot, wonderful host. Had everything we needed, close to town."
United States
Lauren S.
$254 nightly
The price is $290
Aug 4 - Aug 5
Total with taxes and fees
Seapowet suite

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.6 out of 10, Excellent, (7 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
$450 nightly
The price is $503
Aug 2 - Aug 3
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!

Loft Hideaway in Falmouth Village

Loft Hideaway in Falmouth Village
Falmouth
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed our visit!! The location can’t be beat and Falmouth was a great place to explore. "
United States
Nancy F.
$392 nightly
The price is $449
Aug 9 - Aug 10
Total with taxes and fees
Loft Hideaway in Falmouth Village

Ellery Beach Bungalow #45- A Refined Island Escape

Ellery Beach Bungalow #45- A Refined Island Escape
Middletown
10.0 out of 10, Exceptional, (1 review)
"Beautiful area, walking distance to the beach and restaurants, nice clean house"
United States
Dana N.
$414 nightly
The price is $472
Jul 29 - Jul 30
Total with taxes and fees
Ellery Beach Bungalow #45- A Refined Island Escape

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette
Fairhaven
8.4 out of 10, Very Good, (5 reviews)
"The home was beautiful and well equipped. Perfect location in a quiet new england neighborhood. My family enjoyed our stay!"
United States
lea m.
$1,078 nightly
The price is $1,205
Aug 4 - Aug 5
Total with taxes and fees
World Cup Ocean retreat 40 minute drive from Boston Stadium - Gillette

Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (5 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
$1,011 nightly
The price is $1,129
Aug 24 - Aug 25
Total with taxes and fees
Brand New Guest house

Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (8 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
$1,025 nightly
The price is $1,173
Aug 5 - Aug 6
Total with taxes and fees
Elisa's Cottage - Your Family Vacation Destination

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

Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"We enjoyed our stay at this lovely home. The hot tub was very fun and huge kitchen table was nice for our family. It was conveniently located and well cleaned before our arrival. We recommend this fun spot in Newport."
United States
Michelle N.
$985 nightly
The price is $1,071
Aug 4 - Aug 5
Total with taxes and fees
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cuttyhunk Hotel Reviews

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 $503 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This vacation home near Cuttyhunk is located in the city center and has a garden, a barbecue grill, and air-conditioning 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 Horseneck Beach State Reservation 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.