Cuttyhunk Vacation Rentals

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Check prices for these dates

Our top choices for Cuttyhunk vacation rentals

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is CA $220
CA $812 total
includes taxes & fees
Nov 10 - Nov 11
Backyard Retreat / 5 Min > Beach & Main St

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

Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Dartmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Near ButtonWood Park. Quiet neighborhood. Enjoyed my stay."
United States
richard m.
The price is CA $167
CA $416 total
includes taxes & fees
Nov 11 - Nov 12
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!

3. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is CA $494
CA $728 total
includes taxes & fees
Nov 24 - Nov 25
Charming cottage overlooking the bay in Padanaram Village.

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

Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi
New Bedford
9.8 out of 10, Exceptional, (11 reviews)
"The apartment was very roomy. We had a small issue with the stove and the owners responded immediately! The price was great. Ill be back to new bedford and will stay here again"
United States
cricket d.
The price is CA $150
CA $482 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 3-bedroom apartment in enjoyable New Bedford with AC, WiFi

5. Lovely 4- Bedroom apartment for rent

Lovely 4- Bedroom apartment for rent
New Bedford
6.8 out of 10, (3 reviews)
"Stay was great! "
United States
Zoe D.
The price is CA $154
CA $488 total
includes taxes & fees
Nov 16 - Nov 17
Lovely 4- Bedroom apartment for rent

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

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"Beautiful and relaxing location."
United States
Lauren F.
The price is CA $318
CA $677 total
includes taxes & fees
Nov 30 - Dec 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

7. Lovely 3 bedroom apartment 3rd floor

Lovely 3 bedroom apartment 3rd floor
New Bedford
9.4 out of 10, Exceptional, (13 reviews)
"Nice place for staying when traveling to Massachusetts "
United States
Anonymous traveller
The price is CA $146
CA $477 total
includes taxes & fees
Nov 11 - Nov 12
Lovely 3 bedroom apartment 3rd floor

8. The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (49 reviews)
"Lovely flat in a convenient part of town with lots of supermarket and facilities nearby. We loved our stay."
United States
Thomas C.
The price is CA $121
CA $299 total
includes taxes & fees
Nov 10 - Nov 11
The Charming Gem Near The Water!

9. Seapowet suite

Seapowet suite
Tiverton
9.0 out of 10, Wonderful, (15 reviews)
"Beautiful area Wonderful accommodationsPlenty of space and welcoming host! "
United States
Dena E.
The price is CA $177
CA $221 total
includes taxes & fees
Nov 10 - Nov 11
Seapowet suite

10. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (38 reviews)
"Ideal property to enjoy all Middletown & Newport have to offer!"
United States
kelly k.
The price is CA $126
CA $714 total
includes taxes & fees
Nov 18 - Nov 19
Beach house walking distance to Second Beach

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

Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan
Middletown
9.6 out of 10, Exceptional, (21 reviews)
"Apartment was beautiful in a great location!!!"
United States
cathy g.
The price is CA $244
CA $619 total
includes taxes & fees
Nov 15 - Nov 16
Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan

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

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is CA $372
CA $891 total
includes taxes & fees
Nov 11 - Nov 12
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (14 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is CA $218
CA $555 total
includes taxes & fees
Nov 15 - Nov 16
Walk to Beach & Lighthouse: Oak Bluffs Studio!

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

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
The price is CA $181
CA $391 total
includes taxes & fees
Nov 15 - Nov 16
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.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

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

4br & 2ba Ranch style house w/ huge backyard!
PORTSMOUTH
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic spot - house was great for visiting with family. Basemen is a great spot for kids to escape. "
United States
Emo C.
The price is CA $424
CA $868 total
includes taxes & fees
Nov 10 - Nov 11
4br & 2ba Ranch style house w/ huge backyard!

17. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is CA $359
CA $687 total
includes taxes & fees
Nov 10 - Nov 11
Vineyard Luxury "Yurt"

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

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is CA $380
CA $999 total
includes taxes & fees
Nov 20 - Nov 21
Oak Bluffs 4BR • 5 Min Drive to Downtown

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

9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan
Middletown
10.0 out of 10, Exceptional, (17 reviews)
"Best stay "
United States
Justin R.
The price is CA $461
CA $966 total
includes taxes & fees
Nov 10 - Nov 11
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

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (227 reviews)
"Great location "
United States
Stephanie B.
The price is CA $254
CA $739 total
includes taxes & fees
Nov 10 - Nov 11
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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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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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk vacation rentals we have selected for you start as low as CA $120 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 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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