Cuttyhunk Vacation Rentals from AED 314: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Cuttyhunk?

Quaint, ranch style home in Oak Bluffs with central air : This vacation home near 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 you can cook with friends or family.

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Our top choices for Cuttyhunk vacation rentals

A residential street with houses, a speed limit sign, a utility pole, and a clear sky.

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

Fairhaven

AED 2,095 total

includes taxes & fees

17 Nov - 18 Nov

A wooden dining table with a lace tablecloth, surrounded by wooden chairs. A potted plant is on the table.

2. Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

Dartmouth

richard m.

AED 1,132 total

includes taxes & fees

5 Dec - 6 Dec

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

New Bedford

cricket d.

AED 1,245 total

includes taxes & fees

15 Nov - 16 Nov

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

4. Lovely 4- Bedroom apartment for rent

New Bedford

Zoe D.

AED 1,256 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Fairhaven

Lauren F.

AED 1,760 total

includes taxes & fees

30 Nov - 1 Dec

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

6. Lovely 3 bedroom apartment 3rd floor

New Bedford

Anonymous traveler

AED 1,233 total

includes taxes & fees

19 Nov - 20 Nov

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

7. The Charming Gem Near The Water!

New Bedford

Thomas C.

AED 777 total

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.

8. Seapowet suite

Tiverton

Lauren S.

AED 557 total

includes taxes & fees

17 Nov - 18 Nov

An outdoor seating area with Adirondack chairs and a stone fire pit.

9. Beach house walking distance to Second Beach

Easton's Point

kelly k.

AED 1,855 total

includes taxes & fees

29 Nov - 30 Nov

Private deck with lounge seating and grill

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

Middletown

cathy g.

AED 1,608 total

includes taxes & fees

1 Dec - 2 Dec

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

11. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

AED 2,342 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Oak Bluffs

Donna R.

AED 1,442 total

includes taxes & fees

15 Nov - 16 Nov

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

Oak Bluffs

AED 990 total

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a front porch, a driveway, and a well-maintained lawn.

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

Tisbury

Adrienne W.

A wooden deck with a built-in bench and a small enclosed area with a door.

15. 4br & 2ba Ranch style house w/ huge backyard!

PORTSMOUTH

Emo C.

AED 2,274 total

includes taxes & fees

15 Nov - 16 Nov

A circular skylight with wooden beams radiating inward, a white air conditioning unit, and three circular windows with greenery views.

16. Vineyard Luxury "Yurt"

Oak Bluffs

David C.

AED 2,228 total

includes taxes & fees

18 Nov - 19 Nov

A beach with large rocks, a sandy shore, and a cliff.

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

Oak Bluffs

Chris S.

AED 2,540 total

includes taxes & fees

21 Nov - 22 Nov

Kitchen island with stools and bright windows

18. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

Middletown

Justin R.

AED 2,482 total

includes taxes & fees

17 Nov - 18 Nov

A single-story house with a front porch, a garage, and a fenced backyard.

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

Falmouth

Stephanie B.

AED 1,921 total

includes taxes & fees

16 Nov - 17 Nov

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Find vacation rentals that suit your style

Top Cuttyhunk Hotel Reviews

A stone building with the name "WAYPOINT" on the facade, surrounded by a parking lot and other buildings.

Fairfield Inn & Suites by Marriott New Bedford

New Bedford

10/10 Excellent

For the first time in many years I was not able to stay with family while visiting New Bedford, Massachusetts during the Thanksgiving holiday. I chose to stay in this hotel due to the proximity to my family's home and the good reviews. I was so happy I chose this hotel. It was clean and modern. The staff were super friendly and they serve a delicious included breakfast. It has a nice heated pool wich we enjoyed, as well as a small gym. The parking was free and safe to park. I wished I've...

Jose

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

Delano Homestead Bed & Breakfast

Fairhaven

10/10 Excellent

Bob

A modern hotel lobby with a sofa, two leather chairs, a coffee table, and artwork on the walls.

Best Western Dartmouth-New Bedford

North Dartmouth

10/10 Excellent

Gary

A rocky beach with people relaxing and fishing.

The Palmer House Inn

Falmouth

10/10 Excellent

My husband and I loved our stay at the antiques-filled Palmer House Inn. We were able to easily walk to the active Main Street and had our choice of excellent restaurants and gift shops to browse. We also walked to the beach (mostly sandy, but with many sharp rocks as you enter the water), rented bikes and rode to a lighthouse, and enjoyed the delicious breakfasts while sitting on the porch in the cooler weather. I would definitely recommend this property to anyone heading to Cape Cod.

Lori

A reception area with a counter, seating, a digital kiosk, and a chalkboard with a menu.

Whaler Inn and Suites

New Bedford

10/10 Excellent

quinn

Vineyard Harbor Motel - Private Beach

Vineyard Haven

10/10 Excellent

Martina

A historic building with a tower, labeled "Queens Bayway," and a gallery named "Osborn & Ruth Gallery."

Inn on the Square

Falmouth

10/10 Excellent

Andrew

A beach with clear blue water, a sandy shore, and a pier with boats. There are blue umbrellas and lounge chairs on the beach.

Falmouth Tides

Falmouth Heights

10/10 Excellent

Luiz

A long, narrow hotel corridor with patterned carpet and beige walls.

Baymont by Wyndham North Dartmouth / Fall River

North Dartmouth

10/10 Excellent

Luana

A white building with a porch, an American flag, and a number "100" on the door.

ShoreWay Acres Inn & Cape Cod Lodging

Falmouth

10/10 Excellent

John

A large, multi-story house with a covered porch and a well-maintained lawn.

Shore Haven Inn

Falmouth

10/10 Excellent

Nicole

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?

Quaint, ranch style home in Oak Bluffs with central air: This vacation home near 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 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 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.

Cuttyhunk Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cuttyhunk vacation rentals

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

2. Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

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

4. Lovely 4- Bedroom apartment for rent

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

6. Lovely 3 bedroom apartment 3rd floor

7. The Charming Gem Near The Water!

8. Seapowet suite

9. Beach house walking distance to Second Beach

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

11. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

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

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

15. 4br & 2ba Ranch style house w/ huge backyard!

16. Vineyard Luxury "Yurt"

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

18. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

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

Find vacation rentals that suit your style

Top Cuttyhunk Hotel Reviews

Fairfield Inn & Suites by Marriott New Bedford

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Cuttyhunk?

What are some of the best vacation home rentals in Cuttyhunk?

What’s there to see and do in Cuttyhunk?

What’s a vacation rental in Cuttyhunk like?