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

1. 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
The price is CA $119
CA $308 total
includes taxes & fees
Aug 13 - Aug 14
The Charming Gem Near The Water!

2. 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, (39 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.
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

3. 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.
The price is CA $439
CA $727 total
includes taxes & fees
Aug 24 - Aug 25
Charming cottage overlooking the bay in Padanaram Village.

4. 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 $271
CA $612 total
includes taxes & fees
Aug 17 - Aug 18
Lovely 3 bedroom apartment 3rd floor

5. 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 $225
CA $552 total
includes taxes & fees
Aug 11 - Aug 12
Lovely 4- Bedroom apartment for rent

6. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (97 reviews)
"We had a wonderful stay!"
United States
Stacey
The price is CA $215
CA $700 total
includes taxes & fees
Sep 8 - Sep 9
Ellery Bungalow #51- Island Calm Near Newport

7. 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 $215
CA $700 total
includes taxes & fees
Sep 8 - Sep 9
Ellery Beach Bungalow #45- A Refined Island Escape

8. 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.
The price is CA $286
CA $418 total
includes taxes & fees
Aug 19 - Aug 20
Seapowet suite

9. 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.
The price is CA $216
CA $701 total
includes taxes & fees
Sep 8 - Sep 9
Ellery Beach Bungalow #47- Relaxed Island Living

10. 1-bedroom apartment in Falmouth, on bike path, close to beach and town

1-bedroom apartment in Falmouth, on bike path, close to beach and town
Falmouth
9.8 out of 10, Exceptional, (10 reviews)
"Fabulous, cozy retreat close to town. "
United States
BOB N.
The price is CA $162
CA $217 total
includes taxes & fees
Aug 24 - Aug 25
1-bedroom apartment in Falmouth, on bike path, close to beach and town

11. 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.
The price is CA $295
CA $624 total
includes taxes & fees
Aug 11 - Aug 12
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

12. Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties

Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties
Middletown
9.0 out of 10, Wonderful, (7 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.
The price is CA $515
CA $986 total
includes taxes & fees
Aug 13 - Aug 14
Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties

13. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is CA $300
CA $799 total
includes taxes & fees
Sep 8 - Sep 9
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

14. 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.
The price is CA $668
CA $1,249 total
includes taxes & fees
Sep 8 - Sep 9
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

15. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is CA $548
CA $975 total
includes taxes & fees
Aug 27 - Aug 28
Brand new! Lovely apartment-Vineyard Haven

16. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is CA $439
CA $1,183 total
includes taxes & fees
Sep 8 - Sep 9
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

17. 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.
The price is CA $690
CA $1,574 total
includes taxes & fees
Aug 24 - Aug 25
Brand New Guest house

18. 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.
The price is CA $215
CA $700 total
includes taxes & fees
Sep 8 - Sep 9
Ellery Bungalow #49 - Minutes from the Sand
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?

4-bedroom house in lovely Edgartown..Centrally located: This vacation home near Cuttyhunk is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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.