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 $118
CA $304 total
includes taxes & fees
Aug 26 - Aug 27
The Charming Gem Near The Water!

2. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (25 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is CA $447
CA $699 total
includes taxes & fees
Sep 15 - Sep 16
Cozy efficiency apartment/heated pool

3. 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 $184
CA $656 total
includes taxes & fees
Aug 26 - Aug 27
Ellery Beach Bungalow #45- A Refined Island Escape

4. 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 $274
CA $618 total
includes taxes & fees
Sep 7 - Sep 8
Brand new! Lovely apartment-Vineyard Haven

5. 3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Mattapoisett
9.6 out of 10, Exceptional, (52 reviews)
"The area was beautiful! We went mid August and the neighborhood had gorgeous flowers blooming everywhere. The beach area was private and so relaxing. Our pup loved exploring the doggy beach. Good area for restaurants too… we really enjoyed Turk’s!"
United States
Helen R.
The price is CA $344
CA $643 total
includes taxes & fees
Sep 6 - Sep 7
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

6. 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 $204
CA $523 total
includes taxes & fees
Aug 31 - Sep 1
Lovely 4- Bedroom apartment for rent

7. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (16 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is CA $482
CA $778 total
includes taxes & fees
Sep 10 - Sep 11
Charming cottage overlooking the bay in Padanaram Village.

8. 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 $184
CA $656 total
includes taxes & fees
Aug 26 - Aug 27
Ellery Bungalow #51- Island Calm Near Newport

9. 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 $243
CA $573 total
includes taxes & fees
Aug 31 - Sep 1
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

10. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is CA $273
CA $1,037 total
includes taxes & fees
Sep 7 - Sep 8
Lovely two bedroom apartment with indoor fireplace

11. 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 $184
CA $656 total
includes taxes & fees
Aug 26 - Aug 27
Ellery Beach Bungalow #47- Relaxed Island Living

12. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $559
CA $1,240 total
includes taxes & fees
Aug 26 - Aug 27
Backyard Retreat / 5 Min > Beach & Main St

13. Spacious, comfortable rooms near beach & Newport

Spacious, comfortable rooms near beach & Newport
Middletown
8.2 out of 10, Very good, (18 reviews)
"Great location in a quiet neighborhood with easy in and out egress. Accomodations very accurately depicted in photos. Competitive pricing, no issues overall. Would definitely recommend."
United States
Kenneth
Spacious, comfortable rooms near beach & Newport

14. 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 $433
CA $1,168 total
includes taxes & fees
Sep 11 - Sep 12
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

15. 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 $482
CA $1,142 total
includes taxes & fees
Sep 12 - Sep 13
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

16. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is CA $516
CA $865 total
includes taxes & fees
Sep 1 - Sep 2
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

17. 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 $311
CA $632 total
includes taxes & fees
Sep 22 - Sep 23
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

18. Seapowet suite

Seapowet suite
Tiverton
9.0 out of 10, Wonderful, (13 reviews)
"Lovely spot, wonderful host. Had everything we needed, close to town."
United States
Lauren S.
The price is CA $337
CA $477 total
includes taxes & fees
Sep 2 - Sep 3
Seapowet suite

19. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very good, (9 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is CA $453
CA $859 total
includes taxes & fees
Aug 30 - Aug 31
Walk to Beach & Lighthouse: Oak Bluffs Studio!

20. 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 $495
CA $1,131 total
includes taxes & fees
Aug 30 - Aug 31
Little Creek Retreat Private hot tub & 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.
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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: Located near Cuttyhunk, this vacation home rental offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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.