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

Cuttyhunk Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Cuttyhunk vacation rentals

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

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
$509 nightly
The price is $568
Oct 26 - Oct 27
Total with taxes and fees
Backyard Retreat / 5 Min > Beach & Main St
A living room with a sofa, armchairs, a coffee table with a plant, a side table with a lamp, and a window with curtains.

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.
$289 nightly
The price is $323
Nov 10 - Nov 11
Total with taxes and fees
Furnished & Flexible – Perfect for Longer Stays in Dartmouth, MA!
Interior

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.
$460 nightly
The price is $514
Nov 3 - Nov 4
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
A living room with a beige sofa, a glass coffee table, and a TV on a wooden cabinet.

4. 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.
$199 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
The Charming Gem Near The Water!
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!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
$520 nightly
The price is $581
Oct 31 - Nov 1
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A red wooden house with a front porch, steps leading to the door, and a garden with various plants and flowers.

6. 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.
$173 nightly
The price is $197
Nov 2 - Nov 3
Total with taxes and fees
Seapowet suite
Room

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

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
$280 nightly
The price is $313
Nov 15 - Nov 16
Total with taxes and fees
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
A modern kitchen with white appliances, a teal dining area, and a fireplace.

8. Ellery Bungalow #49 - Minutes from the Sand

Ellery Bungalow #49 - Minutes from the Sand
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Very close to the beach. Would highly recommend"
United States
Semo A.
$421 nightly
The price is $480
Nov 1 - Nov 2
Total with taxes and fees
Ellery Bungalow #49 - Minutes from the Sand
A patio area with wicker chairs, a small table, and a house with a shingled exterior.

9. Ellery Beach Bungalow #47- Relaxed Island Living

Ellery Beach Bungalow #47- Relaxed Island Living
Middletown
8.6 out of 10, Excellent, (7 reviews)
"Cabin was just as described. It was clean, well furnished and made a great home base for a long weekend."
United States
Jason L.
$480 nightly
The price is $547
Oct 25 - Oct 26
Total with taxes and fees
Ellery Beach Bungalow #47- Relaxed Island Living
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

10. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Fabulous property! Clean and very comfy."
United States
Claudia
$484 nightly
The price is $541
Oct 24 - Oct 25
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
A room with a white bedside table, a lamp, a wicker basket, and a blue chair.

11. Ellery Bungalow #51- Island Calm Near Newport

Ellery Bungalow #51- Island Calm Near Newport
Middletown
9.6 out of 10, Exceptional, (98 reviews)
"We had a wonderful stay!"
United States
Stacey
$466 nightly
The price is $532
Oct 27 - Oct 28
Total with taxes and fees
Ellery Bungalow #51- Island Calm Near Newport
A modern kitchen with dark cabinets, a central island, and a dining area with a wooden table and white chairs.

12. Beach house walking distance to Second Beach

Beach house walking distance to Second Beach
Easton's Point
10.0 out of 10, Exceptional, (36 reviews)
"Great place and very welcoming host. Nearby to second beach in a quiet neighborhood."
United States
Melissa G.
$569 nightly
The price is $649
Oct 25 - Oct 26
Total with taxes and fees
Beach house walking distance to Second Beach
Private kitchen

13. 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
9.6 out of 10, Exceptional, (18 reviews)
"Best stay "
United States
Justin R.
$586 nightly
The price is $636
Oct 25 - Oct 26
Total with taxes and fees
9 Private Acres, Hot Tub & Fire Pit | Sleeps 10 | Pet-Friendly | RIBryan
A modern kitchen with stainless steel appliances, white cabinets, and a dining area set for four.

14. 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.
$571 nightly
The price is $651
Oct 25 - Oct 26
Total with taxes and fees
4br & 2ba Ranch style house w/ huge backyard!
Living area

15. 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.
$426 nightly
The price is $462
Oct 25 - Oct 26
Total with taxes and fees
Water Views, Private Deck & Walk to the Beach | Pet-Friendly | RIBryan
A two-story house with a stone chimney, a red front door, and a porch with white railings.

16. Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan

Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay at this lovely home. The hot tub was very fun and huge kitchen table was nice for our family. It was conveniently located and well cleaned before our arrival. We recommend this fun spot in Newport."
United States
Michelle N.
$577 nightly
The price is $626
Oct 29 - Oct 30
Total with taxes and fees
Hot Tub, Fenced Yard & Fire Pit | Sleeps 8 | Pet-Friendly | RIBryan
A wooden deck with wicker chairs and a round table with a sun design.

17. 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.
$480 nightly
The price is $536
Nov 1 - Nov 2
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A bathroom with a white vanity, a sink, a window with blinds, and a radiator.

18. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
$1,029 nightly
The price is $1,150
Oct 30 - Oct 31
Total with taxes and fees
Delightful 3-bedroom house with AC in Oak Bluffs
Dining

19. 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.
$546 nightly
The price is $610
Nov 11 - Nov 12
Total with taxes and fees
Vineyard Luxury "Yurt"
A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

20. 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.
$675 nightly
The price is $754
Nov 11 - Nov 12
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cuttyhunk Hotel Reviews

Fairfield Inn & Suites by Marriott New Bedford

Fairfield Inn & Suites by Marriott New Bedford

10/10 Excellent
"Clean room. Great staff. Close to a few great restaurants."
Scott 3-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott New Bedford

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 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.

Explore a world of travel with Expedia

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.