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

Cuttyhunk Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Cuttyhunk holiday rentals

Smart TV, stereo

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 HK$670
HK$1,756 total
includes taxes & fees
15 Sept - 16 Sept
The Charming Gem Near The Water!
Outdoor pool, a heated pool

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 HK$2,704
HK$4,203 total
includes taxes & fees
28 Sept - 29 Sept
Cozy efficiency apartment/heated pool
Exterior detail

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 HK$1,050
HK$3,727 total
includes taxes & fees
7 Sept - 8 Sept
Ellery Beach Bungalow #45- A Refined Island Escape
Interior

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 HK$1,552
HK$3,538 total
includes taxes & fees
7 Sept - 8 Sept
Brand new! Lovely apartment-Vineyard Haven
Beach nearby, sun-loungers, beach umbrellas, beach towels

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)
"We had a great stay! The community the home is located in was so quiet. The place was so clean, you would not know it was pet friendly! Our hosts had everything we needed and then some, from extra dog supplies to books to keep our toddler occupied. And our hosts kept the check in, stay and check out instructions simple. We would definitely book this place again!"
United States
Shawn A.
The price is HK$1,960
HK$3,695 total
includes taxes & fees
6 Sept - 7 Sept
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Exterior detail

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 HK$1,303
HK$3,163 total
includes taxes & fees
30 Aug - 31 Aug
Lovely 4- Bedroom apartment for rent
Interior

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 HK$2,469
HK$4,063 total
includes taxes & fees
10 Sept - 11 Sept
Charming cottage overlooking the bay in Padanaram Village.
TV

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 HK$1,050
HK$3,745 total
includes taxes & fees
2 Sept - 3 Sept
Ellery Bungalow #51- Island Calm Near Newport
Living area

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 HK$1,192
HK$3,003 total
includes taxes & fees
31 Aug - 1 Sept
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
Property grounds

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 HK$1,544
HK$5,875 total
includes taxes & fees
7 Sept - 8 Sept
Lovely two bedroom apartment with indoor fireplace
Property grounds

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 HK$1,050
HK$3,744 total
includes taxes & fees
2 Sept - 3 Sept
Ellery Beach Bungalow #47- Relaxed Island Living
Interior

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
Backyard Retreat / 5 Min > Beach & Main St
Beach

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
The price is HK$1,160
HK$1,903 total
includes taxes & fees
21 Sept - 22 Sept
Spacious, comfortable rooms near beach & Newport
TV, fireplace, books

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 HK$2,469
HK$6,655 total
includes taxes & fees
11 Sept - 12 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Exterior

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 HK$2,743
HK$6,505 total
includes taxes & fees
12 Sept - 13 Sept
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
Interior

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 HK$2,939
HK$4,956 total
includes taxes & fees
6 Sept - 7 Sept
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Smart TV

17. Middletown Modern Apartment w/ Private Deck - RIBryan Properties

Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Middletown
9.6 out of 10, Exceptional, (18 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is HK$1,661
HK$3,528 total
includes taxes & fees
22 Sept - 23 Sept
Middletown Modern Apartment w/ Private Deck - RIBryan Properties
Terrace/patio

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 HK$1,920
HK$2,761 total
includes taxes & fees
28 Sept - 29 Sept
Seapowet suite
Terrace/patio

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 HK$2,579
HK$4,912 total
includes taxes & fees
30 Aug - 31 Aug
Walk to Beach & Lighthouse: Oak Bluffs Studio!
Coffee/tea maker, fridge, microwave, oven

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, (16 reviews)
"Best stay "
United States
Justin R.
The price is HK$3,808
HK$7,653 total
includes taxes & fees
22 Sept - 23 Sept
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"I thought my room was super sweet! Loved the view and i felt secluded up on 2nd floor far corner! Loved the private beach! Only improvement is maybe property is a bit old? But loved meaning i think room needed a paint job and some updates? But loved every minute! Staff very friendly! Loved location!"
Margaret 2-night trip
Posted 7 hours ago
Vineyard Harbor Motel - Private Beach

Find out more about Cuttyhunk

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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 offers a patio, a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 Horseneck Beach State Reservation 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.