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

Cuttyhunk Vacation Rentals

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Our top choices for Cuttyhunk vacation rentals

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is CA $340
CA $705 total
includes taxes & fees
Jul 14 - Jul 15
The Sky-High Beach House: Panoramic Waterfront views

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (43 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 CA $121
CA $313 total
includes taxes & fees
Jul 21 - Jul 22
The Charming Gem Near The Water!

Convenient and clean studio near the beach and Newport.

Convenient and clean studio near the beach and Newport.
Middletown
9.2 out of 10, Wonderful, (20 reviews)
"Meets basic needs if your staying a night or two. "
United States
Michael M.
The price is CA $213
CA $346 total
includes taxes & fees
Jul 13 - Jul 14
Convenient and clean studio near the beach and Newport.

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)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is CA $333
CA $733 total
includes taxes & fees
Jul 15 - Jul 16
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

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 CA $300
CA $638 total
includes taxes & fees
Jul 13 - Jul 14
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

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.
The price is CA $234
CA $738 total
includes taxes & fees
Jul 13 - Jul 14
Ellery Bungalow #51- Island Calm Near Newport

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.
The price is CA $195
CA $516 total
includes taxes & fees
Jul 13 - Jul 14
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.4 out of 10, Exceptional, (13 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveller
The price is CA $215
CA $544 total
includes taxes & fees
Jul 12 - Jul 13
Lovely 3 bedroom apartment 3rd floor

Seapowet suite

Seapowet suite
Tiverton
10.0 out of 10, Exceptional, (11 reviews)
"Lovely spot, wonderful host. Had everything we needed, close to town."
United States
Lauren S.
The price is CA $300
CA $432 total
includes taxes & fees
Jul 12 - Jul 13
Seapowet suite

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.
The price is CA $221
CA $721 total
includes taxes & fees
Jul 13 - Jul 14
Ellery Beach Bungalow #45- A Refined Island Escape

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 CA $236
CA $567 total
includes taxes & fees
Jul 13 - Jul 14
Lovely 4- Bedroom apartment for rent

Spacious, comfortable rooms near beach & Newport

Spacious, comfortable rooms near beach & Newport
Middletown
8.0 out of 10, Very good, (16 reviews)
"Great stay - great location! "
United States
Jana D.
The price is CA $210
CA $342 total
includes taxes & fees
Jul 15 - Jul 16
Spacious, comfortable rooms near beach & Newport

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (30 reviews)
"Great house and communication with the owner! We would stay there again!"
United States
Stan C.
The price is CA $381
CA $1,048 total
includes taxes & fees
Jul 12 - Jul 13
Beach house walking distance to Second Beach

Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
9.4 out of 10, Exceptional, (6 reviews)
The price is CA $238
CA $745 total
includes taxes & fees
Jul 28 - Jul 29
Ellery Beach Bungalow #47- Relaxed Island Living

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.
The price is CA $425
CA $723 total
includes taxes & fees
Jul 27 - Jul 28
Small One Bedroom Private Cottage on Large Quiet Property.

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.4 out of 10, (8 reviews)
"This house was perfect. Super cute interior, well outfitted beds, plenty of space for our large family (2 adults, 4 kids, 1 small dog) - bonus points for the big laundry machines. Extra points for the super helpful and responsive host who went out of his way for us - even when I was messaging late at night on a Saturday after my daughter took a fall in Edgartown and had to be transported to Vineyard Hospital by ambulance. We will definitely rent this house again. Highly recommend!! "
United States
Nicole L.
The price is CA $286
CA $800 total
includes taxes & fees
Jul 12 - Jul 13
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Absolutely incredible stay! The host is so kind and helpful. House was very clean. Truly everything you need inside for cooking and beach fun! PERFECT location really centrally located to both edgartown and oak bluffs. Located in a quiet neighborhood near Felix Neck with lots of walking trails, which was very nice! Could not recommend this place more!"
United States
Katelyn W.
The price is CA $893
CA $2,043 total
includes taxes & fees
Jul 21 - Jul 22
4-bedroom house in lovely Edgartown..Centrally located

Pop, Bubble, and sun-drenched Cutie Cottage!

Pop, Bubble, and sun-drenched Cutie Cottage!
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We loved our stay! The cottage was the perfect size for what we needed and a great location! We would definitely stay again."
United States
Lauren C.
The price is CA $339
CA $691 total
includes taxes & fees
Jul 27 - Jul 28
Pop, Bubble, and sun-drenched Cutie Cottage!

Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $469
CA $1,142 total
includes taxes & fees
Jul 15 - Jul 16
Backyard Retreat / 5 Min > Beach & Main St

Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
The price is CA $355
CA $978 total
includes taxes & fees
Jul 13 - Jul 14
Charming Guesthouse | Walk to Beach | Downtown
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 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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk vacation rentals we have selected for you start as low as CA $1,355 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 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. 

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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 rental 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 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.