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

Cuttyhunk Vacation Rentals

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Check prices for these dates, December 13 – 14, 2026

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Our top choices for Cuttyhunk vacation rentals

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

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

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

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

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

Living area

4. Lovely 4- Bedroom apartment for rent

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

5. Lovely 3 bedroom apartment 3rd floor

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

6. The Charming Gem Near The Water!

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

7. Seapowet suite

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

8. Beach house walking distance to Second Beach

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

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

Living room looking toward the dining area and deck

10. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

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

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

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

A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

13. 4br & 2ba Ranch style house w/ huge backyard!

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

14. Vineyard Luxury "Yurt"

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.

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

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

16. 9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan

Kitchen island with stools and bright windows

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

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

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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Cottages

Apartments

Aparthotels

Condos

Top Cuttyhunk Hotel Reviews

Fairfield Inn & Suites by Marriott New Bedford

A hotel entrance with a covered driveway, a white van parked in front, and a stone building facade.

Delano Homestead Bed & Breakfast

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

Shore Haven Inn

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

The Palmer House Inn

An outdoor patio with a fire table, seating, and a table set for a meal.

Best Western Dartmouth-New Bedford

A modern restaurant with wooden flooring, blue upholstered chairs, and a central island with a counter.

New Bedford Harbor Hotel

A hotel room with a large bed, a desk, and a view of a cityscape through the window.

Vineyard Harbor Motel - Private Beach

A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.

Falmouth Tides

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

Inn on the Square

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

Whaler Inn and Suites

A pub interior with a sign for Ryan's Pub, a pick-up area, and a bar visible through the open door.

Baymont by Wyndham North Dartmouth / Fall River

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

ShoreWay Acres Inn & Cape Cod Lodging

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

Find out more about Cuttyhunk

Everything you need to know about Cuttyhunk vacation rentals

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

Cuttyhunk vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cuttyhunk in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cuttyhunk rentals

At Expedia, we put the best Cuttyhunk vacation 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 vacation.

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 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.

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