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

Holiday Rentals in Cuttyhunk

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Our top choices for Cuttyhunk holiday 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 €203
includes taxes & fees
6 Sept - 7 Sept
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.
The price is €407
includes taxes & fees
10 Aug - 11 Aug
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 €492
includes taxes & fees
24 Aug - 25 Aug
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 €412
includes taxes & fees
17 Aug - 18 Aug
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 €402
includes taxes & fees
20 Aug - 21 Aug
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, (96 reviews)
"This was the perfect size and location for our group of 5, would definitely stay again! "
United States
toni g.
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.
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 €264
includes taxes & fees
19 Aug - 20 Aug
Seapowet suite

9. 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)
"My wife and I really enjoyed our stay. This Cottage is the perfect size for a couple. We enjoyed the beautiful quiet setting that was close to town. The host thought of everything and the cottage was so clean it felt like we were the first people who ever rented the unit. We walked into town several times and loved the location. Do not hesitate to rent this cottage. "
United States
Timothy G.
The price is €443
includes taxes & fees
23 Aug - 24 Aug
Small One Bedroom Private Cottage on Large Quiet Property.

10. 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.
Ellery Beach Bungalow #47- Relaxed Island Living

11. 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 €135
includes taxes & fees
24 Aug - 25 Aug
1-bedroom apartment in Falmouth, on bike path, close to beach and town

12. 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 €455
includes taxes & fees
2 Sept - 3 Sept
Middletown Modern Apartment w/ Private Deck - RIBryan Properties

13. 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 €510
includes taxes & fees
9 Aug - 10 Aug
Middletown Modern Townhouse w/Private Fenced Yard - RIBryan Properties

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.8 out of 10, Excellent, (8 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is €543
includes taxes & fees
22 Aug - 23 Aug
Walk to Beach & Lighthouse: Oak Bluffs Studio!

15. 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 €539
includes taxes & fees
1 Sept - 2 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

16. 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.
Middletown Bungalow w/Hot Tub and Private Yard - RIBryan Properties

17. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
The price is €654
includes taxes & fees
27 Aug - 28 Aug
Brand new! Lovely apartment-Vineyard Haven

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (7 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is €1,333
includes taxes & fees
5 Sept - 6 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

19. 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 €981
includes taxes & fees
24 Aug - 25 Aug
Brand New Guest house

20. 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.
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

Everything you need to know about Cuttyhunk holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cuttyhunk holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cuttyhunk holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk holiday rentals we have selected for you start as low as €135 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 holiday 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 holiday.

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 holiday rental in Cuttyhunk?

Yes, there are holiday rentals close to the most popular sights in Cuttyhunk, or you can select a more secluded option if you're looking for a relaxing stay. Cuttyhunk is known for its beaches.

What are some of the best holiday rentals that Cuttyhunk has to offer?

4-bedroom house in lovely Edgartown..Centrally located: This holiday home rental outside of 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 wider area.

What’s a holiday rental in Cuttyhunk like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cuttyhunk. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.