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 Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (41 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 $318 total
includes taxes & fees
Jun 29 - Jun 30
The Charming Gem Near The Water!

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 $295
CA $627 total
includes taxes & fees
Jun 28 - Jun 29
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is CA $368
CA $742 total
includes taxes & fees
Jul 14 - Jul 15
The Sky-High Beach House: Panoramic Waterfront views

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 $734 total
includes taxes & fees
Jul 15 - Jul 16
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

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 CA $286
CA $420 total
includes taxes & fees
Jul 7 - Jul 8
Seapowet suite

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 $195
CA $520 total
includes taxes & fees
Jun 28 - Jun 29
Lovely 3 bedroom apartment 3rd floor

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 $189
CA $510 total
includes taxes & fees
Jun 28 - Jun 29
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

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 $345 total
includes taxes & fees
Jul 15 - Jul 16
Convenient and clean studio near the beach and Newport.

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

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Westport
9.6 out of 10, Exceptional, (45 reviews)
"Super quiet and private neighborhood which makes for great walks!"
United States
Caitlin J.
The price is CA $429
CA $548 total
includes taxes & fees
Jul 14 - Jul 15
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

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 $270
CA $613 total
includes taxes & fees
Jun 28 - Jun 29
Lovely 4- Bedroom apartment for rent

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 CA $413
CA $1,042 total
includes taxes & fees
Jun 29 - Jun 30
Little Creek Retreat Private hot tub & yard - RIBryan Properties

Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
9.8 out of 10, Exceptional, (28 reviews)
"Great house and communication with the owner! We would stay there again!"
United States
Stan C.
The price is CA $382
CA $1,050 total
includes taxes & fees
Jun 28 - Jun 29
Beach house walking distance to Second Beach

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is CA $669
CA $1,417 total
includes taxes & fees
Jul 11 - Jul 12
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (1 review)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
The price is CA $1,277
CA $2,535 total
includes taxes & fees
Jul 19 - Jul 20
4-bedroom house in lovely Edgartown..Centrally located

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 $211
CA $342 total
includes taxes & fees
Jul 15 - Jul 16
Spacious, comfortable rooms near beach & Newport

LUX on Main | Downtown | Parking | Sleeps 6, #203

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
The price is CA $423
CA $1,204 total
includes taxes & fees
Jun 29 - Jun 30
LUX on Main | Downtown | Parking | Sleeps 6, #203

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 $280
CA $802 total
includes taxes & fees
Jul 21 - Jul 22
Ellery Bungalow #51- Island Calm Near Newport

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Dartmouth
The price is CA $167
CA $441 total
includes taxes & fees
Jul 9 - Jul 10
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (7 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is CA $597
CA $1,338 total
includes taxes & fees
Jun 29 - Jun 30
Elisa's Cottage - Your Family Vacation Destination

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 $197
CA $686 total
includes taxes & fees
Jun 28 - Jun 29
Ellery Beach Bungalow #47- Relaxed Island Living
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.