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 27 - Jul 28
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 $297
CA $434 total
includes taxes & fees
Jul 14 - Jul 15
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)
"Fantastic stay! "
United States
Cristin C.
The price is CA $237
CA $743 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cuttyhunk. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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.