Cuttyhunk Holiday Rentals from NZ$281: Search Short-Term Rentals

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

Quaint, ranch style home in Oak Bluffs with central air : This holiday home rental outside of Cuttyhunk is located near the beach, and has a balcony, a garden and air conditioning to put you at ease 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.

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Our top choices for Cuttyhunk holiday rentals

A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

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

Fairhaven

includes taxes & fees

10 Nov - 11 Nov

A living room with a sofa, armchairs, a coffee table with a plant, a side table with a lamp, and a window with curtains.

2. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

Dartmouth

richard m.

includes taxes & fees

11 Nov - 12 Nov

3. Charming cottage overlooking the bay in Padanaram Village.

Dartmouth

Judith M.

includes taxes & fees

24 Nov - 25 Nov

4. Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

New Bedford

cricket d.

includes taxes & fees

10 Nov - 11 Nov

A two-story building with a covered porch and steps leading to the entrance.

5. Lovely 4- Bedroom apartment for rent

New Bedford

Zoe D.

includes taxes & fees

19 Nov - 20 Nov

A patio with outdoor furniture, a tree, and a lattice fence.

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

Fairhaven

Lauren F.

includes taxes & fees

30 Nov - 1 Dec

A living room with a television, sofa, and wooden columns.

7. Lovely 3 bedroom apartment 3rd floor

New Bedford

Anonymous traveller

includes taxes & fees

15 Nov - 16 Nov

A living room with a beige sofa, a glass coffee table, and a TV on a wooden cabinet.

8. The Charming Gem Near The Water!

New Bedford

Thomas C.

includes taxes & fees

15 Nov - 16 Nov

A red wooden house with a front porch, steps leading to the door, and a garden with various plants and flowers.

9. Seapowet suite

Tiverton

Dena E.

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

10. Beach house walking distance to Second Beach

Easton's Point

kelly k.

includes taxes & fees

18 Nov - 19 Nov

Living room looking toward the dining area and deck

11. Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan

Middletown

cathy g.

includes taxes & fees

15 Nov - 16 Nov

A circular stone patio with Adirondack chairs and a small table in a forested area.

12. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

includes taxes & fees

10 Nov - 11 Nov

An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Oak Bluffs

Donna R.

includes taxes & fees

15 Nov - 16 Nov

14. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Oak Bluffs

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with wicker chairs and a round table with a sun design.

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

Tisbury

Adrienne W.

A modern kitchen with stainless steel appliances, white cabinets, and a dining area set for four.

16. 4br & 2ba Ranch style house w/ huge backyard!

PORTSMOUTH

Emo C.

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

17. Vineyard Luxury "Yurt"

Oak Bluffs

David C.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

18. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs

Chris S.

includes taxes & fees

20 Nov - 21 Nov

Kitchen island with stools and bright windows

19. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

Middletown

Justin R.

includes taxes & fees

10 Nov - 11 Nov

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

20. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth

Stephanie B.

includes taxes & fees

10 Nov - 11 Nov

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Find holiday rentals that suit your style

Top Cuttyhunk Hotel Reviews

A two-story house with a front porch, a stone wall, and a well-maintained garden.

Delano Homestead Bed & Breakfast

Fairhaven

10/10 Excellent

Helen

A balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.

Mansion House Inn And Spa

Vineyard Haven

10/10 Excellent

Anonymous traveller

A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.

Inn on the Square

Falmouth

8/10 Good

Barry

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, 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 NZ$281 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.

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?

Quaint, ranch style home in Oak Bluffs with central air: This holiday home rental outside of Cuttyhunk is located near the beach, and has a balcony, a garden and air conditioning to put you at ease 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.

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.

Cuttyhunk Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cuttyhunk holiday rentals

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

2. Cozy Autumn Escape Near Fall Foliage in Dartmouth, MA

3. Charming cottage overlooking the bay in Padanaram Village.

4. Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

5. Lovely 4- Bedroom apartment for rent

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

7. Lovely 3 bedroom apartment 3rd floor

8. The Charming Gem Near The Water!

9. Seapowet suite

10. Beach house walking distance to Second Beach

11. Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan

12. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

14. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

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

16. 4br & 2ba Ranch style house w/ huge backyard!

17. Vineyard Luxury "Yurt"

18. Oak Bluffs 4BR • 5 Min Drive to Downtown

19. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

20. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Find holiday rentals that suit your style

Top Cuttyhunk Hotel Reviews

Delano Homestead Bed & Breakfast

10/10 Excellent

Find out more about Cuttyhunk

Cuttyhunk holiday rentals: An excellent choice for every season

How to find incredible deals on Cuttyhunk rentals

Frequently Asked Questions

Can I find a holiday rental in Cuttyhunk?

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

What’s there to see and do in Cuttyhunk?

What’s a holiday rental in Cuttyhunk like?

Explore a world of travel with Expedia