Cuttyhunk Vacation Rentals from $159: Search Short-Term Rentals

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

Gorgeous Spacious Victorian Cape Cod Beach View Retreat : Located near Cuttyhunk, this vacation home rental 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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Our top choices for Cuttyhunk vacation rentals

1. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

$858 nightly

Sep 1 - Sep 2

Total with taxes and fees

2. The Charming Gem Near The Water!

New Bedford

Thomas

$201 nightly

Aug 26 - Aug 27

Total with taxes and fees

3. Cozy efficiency apartment/heated pool

Chilmark

Clifford L.

$485 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Charming cottage overlooking the bay in Padanaram Village.

Dartmouth

Cathie K.

$469 nightly

Aug 24 - Aug 25

Total with taxes and fees

5. Lovely two bedroom apartment with indoor fireplace

Oak Bluffs

Aviva M.

$667 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Middletown

Dana N.

$445 nightly

Sep 8 - Sep 9

Total with taxes and fees

7. Ellery Bungalow #51- Island Calm Near Newport

Middletown

Stacey

$445 nightly

Sep 8 - Sep 9

Total with taxes and fees

8. Lovely 3 bedroom apartment 3rd floor

New Bedford

Anonymous traveler

$383 nightly

Aug 16 - Aug 17

Total with taxes and fees

9. Lovely 4- Bedroom apartment for rent

New Bedford

Zoe D.

$361 nightly

Aug 13 - Aug 14

Total with taxes and fees

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

Oak Bluffs

Karen M.

$760 nightly

Sep 8 - Sep 9

Total with taxes and fees

11. Ellery Beach Bungalow #47- Relaxed Island Living

Middletown

Cristin C.

$442 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Middletown

cathy g.

$493 nightly

Aug 13 - Aug 14

Total with taxes and fees

13. Seapowet suite

Tiverton

Lauren S.

$289 nightly

Aug 19 - Aug 20

Total with taxes and fees

14. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Bethann N.

$640 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Tisbury

Adrienne W.

$480 nightly

Sep 2 - Sep 3

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

16. Brand New Guest house

Oak Bluffs

Elizabeth O.

$914 nightly

Sep 7 - Sep 8

Total with taxes and fees

17. Charming Vacation Home in Oak Bluffs.

Oak Bluffs

$856 nightly

Sep 8 - Sep 9

Total with taxes and fees

18. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs

Sherri R.

$1,249 nightly

Sep 6 - Sep 7

Total with taxes and fees

19. Ellery Bungalow #49 - Minutes from the Sand

Middletown

Semo A.

$445 nightly

Sep 8 - Sep 9

Total with taxes and fees

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Top Cuttyhunk Hotel Reviews

Whaler Inn and Suites

8/10 Good

"Clean room but ADA rooms are furthest away from lobby/restaurant. Not a very smooth wheelchair transition from parking lot to sidewalk and room entry."

Vineyard Harbor Motel - Private Beach

10/10 Excellent

"This is my second time staying at VHM. I was attending a conference and the location was great. The motel is just a few blocks around the corner from the Vineyard Haven ferry which makes it so convenient for travel. The rooms appear to have been remodeled since last year’s stay, which was a nice surprise. The gentleman who sits at the front desk is always warm and welcoming. The bus stops outside the motel and there are a lot of shops across the street. There is a private beach in the back which I unfortunately didn’t get a chance to enjoy this year. I do plan to stay again next year!"

Town & Beach Motel

10/10 Excellent

"My daughter and I stayed at the Town and Beach Motel last week. It is close to the shopping and restaurants in downtown Falmouth. The woman who checked us in was very friendly and gave us some tips on where to find the best lobster roll in town and where to get coffee in the morning. Our room was clean and the air conditioner worked great. Parking is free and food and shopping is in a very walkable distance. Would stay there again."

Best Western Dartmouth-New Bedford

10/10 Excellent

"The place was very good and the staff I met were excellent. I will be back. The property however needs immediate attention. It's understandable that the building itself might always need some upkeep, (heavy water damage had collapsed part of the front overhang), but finding, and more importantly leaving the entrance is outright dangerous. The hotel sign is not visible from the road, (only from INSIDE the parking lot),and the entrance sign is not visible at all until right at it. Leaving in a small vehicle is extremely risky due to shrubs and the nose of the car must be in the traffic lane before even seeing that it's safe to leave. It appears that this has been neglected for years. This is such a small item for such a big chain that the continuation of the problem is inexcusable. I can only hope that the situation has not resulted in personal injury, but that could only happen with the vigilance of those who are traveling on the roadway to move out of the way or stop beforehand."

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 $159 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: Located near Cuttyhunk, this vacation home rental 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 Demarest Lloyd State Park 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. Walk to Beach! Oak Bluffs Home & Studio

2. The Charming Gem Near The Water!

3. Cozy efficiency apartment/heated pool

4. Charming cottage overlooking the bay in Padanaram Village.

5. Lovely two bedroom apartment with indoor fireplace

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

7. Ellery Bungalow #51- Island Calm Near Newport

8. Lovely 3 bedroom apartment 3rd floor

9. Lovely 4- Bedroom apartment for rent

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. Seapowet suite

14. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

16. Brand New Guest house

17. Charming Vacation Home in Oak Bluffs.

18. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

19. Ellery Bungalow #49 - Minutes from the Sand

Find vacation rentals that suit your style

Top Cuttyhunk Hotel Reviews

Whaler Inn and Suites

Find out more about Cuttyhunk

Explore a world of travel with Expedia

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