Cuttyhunk Vacation Rentals from $849: Search Short-Term Rentals

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

Gorgeous Spacious Victorian Cape Cod Beach View Retreat : This vacation home rental near Cuttyhunk is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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In two weeks

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Our top choices for Cuttyhunk vacation rentals

1. Cozy efficiency apartment/heated pool

Chilmark

Jillian G.

$451 nightly

Sep 9 - Sep 10

Total with taxes and fees

2. The Charming Gem Near The Water!

New Bedford

Thomas

$199 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Dartmouth

richard m.

$289 nightly

Sep 25 - Sep 26

Total with taxes and fees

4. Charming cottage overlooking the bay in Padanaram Village.

Dartmouth

Judith M.

$463 nightly

Sep 10 - Sep 11

Total with taxes and fees

5. Lovely 4- Bedroom apartment for rent

New Bedford

Zoe D.

$319 nightly

Sep 10 - Sep 11

Total with taxes and fees

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

Fairhaven

Jainessa

$452 nightly

Sep 30 - Oct 1

Total with taxes and fees

7. Ellery Beach Bungalow #45- A Refined Island Escape

Middletown

Dana N.

$420 nightly

Sep 9 - Sep 10

Total with taxes and fees

8. Ellery Bungalow #51- Island Calm Near Newport

Middletown

Stacey

$468 nightly

Sep 24 - Sep 25

Total with taxes and fees

9. Spacious, comfortable rooms near beach & Newport

Middletown

Kenneth

$213 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Oak Bluffs

Karen M.

$760 nightly

Sep 11 - Sep 12

Total with taxes and fees

11. Ellery Beach Bungalow #47- Relaxed Island Living

Middletown

Cristin C.

$466 nightly

Sep 14 - Sep 15

Total with taxes and fees

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

Middletown

cathy g.

$425 nightly

Oct 5 - Oct 6

Total with taxes and fees

13. Beach house walking distance to Second Beach

Easton's Point

Kelley

$598 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Middletown

Michelle N.

$625 nightly

Sep 9 - Sep 10

Total with taxes and fees

15. Ellery Bungalow #49 - Minutes from the Sand

Middletown

Semo A.

$420 nightly

Sep 9 - Sep 10

Total with taxes and fees

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

Tisbury

Adrienne W.

$487 nightly

Sep 18 - Sep 19

Total with taxes and fees

17. Seapowet suite

Tiverton

Lauren S.

$309 nightly

Sep 15 - Sep 16

Total with taxes and fees

18. Brand New Guest house

Oak Bluffs

Elizabeth O.

$857 nightly

Oct 1 - Oct 2

Total with taxes and fees

19. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Bethann N.

$640 nightly

Sep 9 - Sep 10

Total with taxes and fees

20. LUX on Main | Downtown | Parking | Sleeps 6, #203

Falmouth

$726 nightly

Sep 9 - Sep 10

Total with taxes and fees

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Top Cuttyhunk Hotel Reviews

Seaport Resort & Marina

8/10 Good

"The first room that we were checked into was unacceptable. The beds were hard. There was no blind on the window that would’ve kept people from seeing in with the lights on. The music on the weekends is really loud. We requested a room in the front of the building and were moved when we checked in, and after that everything was acceptable. The staff is very sparse, but helpful. I would stay there again, but I would insist on a room upfront."

Best Western Dartmouth-New Bedford

10/10 Excellent

"I would stay here again without a doubt! The room was perfectly designed for vacation and work - a desk, easy chair and ottoman, fridge and microwave, and lots of space. The bathroom design was equally big and well-thought out: lots of counter space, and space to move around the toilet, tub, and sink (vs. when they’re right next to each other and it seems as if you’re using all at once). When you’re at a hotel, you want it to work efficiently and not have to waste time rearranging or working against the space. This space works for you, and the breakfast was super delicious! Protein-heavy (mini omelettes, sausages and french toast or pancakes), it was a perfect way to start the day. The staff were very friendly and helpful. The parking lot was also safe. I hope I get the chance to return there."

Vineyard Harbor Motel - Private Beach

10/10 Excellent

"We had a fantastic stay here. The property was spotless, reasonably priced, and situated in an ideal, walkable location with easy access to local shops and restaurants. The private beach access and the deck overlooking the harbor boats really elevated the whole experience. A special shoutout to the front desk manager from South Africa—I am terrible with names and wish I could remember his, but he was fantastic. We had several great conversations with him, and every single restaurant recommendation he gave was spot-on. Our only minor critique was the lack of drinking cups in the room, but the fact that this was our biggest complaint says a lot about the quality of the stay. We would gladly come back and highly recommend it!"

New Bedford Harbor Hotel

8/10 Good

"Conveniently located in walking distance of the Harbour and restaurants. The rooms and bathrooms are spacious and comfortable, though minimalistic. There is street parking if you are lucky; we were. Otherwise paid parking is a mile from the hotel. We were just passing through but would gladly return for a longer stay."

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 $849 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.

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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?

Gorgeous Spacious Victorian Cape Cod Beach View Retreat: This vacation home rental near Cuttyhunk is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 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

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Check prices for these dates

Our top choices for Cuttyhunk vacation rentals

1. Cozy efficiency apartment/heated pool

2. The Charming Gem Near The Water!

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

4. Charming cottage overlooking the bay in Padanaram Village.

5. Lovely 4- Bedroom apartment for rent

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

7. Ellery Beach Bungalow #45- A Refined Island Escape

8. Ellery Bungalow #51- Island Calm Near Newport

9. Spacious, comfortable rooms near beach & Newport

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

11. Ellery Beach Bungalow #47- Relaxed Island Living

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

13. Beach house walking distance to Second Beach

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

15. Ellery Bungalow #49 - Minutes from the Sand

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

17. Seapowet suite

18. Brand New Guest house

19. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

20. LUX on Main | Downtown | Parking | Sleeps 6, #203

Find vacation rentals that suit your style

Top Cuttyhunk Hotel Reviews

Seaport Resort & Marina

Find out more about Cuttyhunk

Explore a world of travel with Expedia

Frequently asked questions

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