Holiday Rentals in Cuttyhunk

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Holiday Rentals in Cuttyhunk

Our top choices for Cuttyhunk holiday rentals

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
Exterior

Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards

9.8 out of 10, Exceptional, (153)
"Will definitely be back, sooner than later! Excellent stay!"
The price is €168
includes taxes & fees
8 Oct - 9 Oct
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (177)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Exterior

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.6 out of 10, (29)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
Walk to beach! Great large outdoor patio. Still booking fall 2025!
Outdoor dining

Walk to beach! Great large outdoor patio. Still booking fall 2025!

10.0 out of 10, Exceptional, (106)
"Rebecca’s place was lovely and clean. We were in town for a wedding but would come back to enjoy a weekend by the beach. Walking distance to great restaurants and the beach and the side patio was a great spot to relax."
Walk to beach! Great large outdoor patio. Still booking fall 2025!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
Fridge, microwave, oven, stovetop

Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.

10.0 out of 10, Exceptional, (99)
"Very enjoyable "
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
Cozy Beach Cottage
Beach nearby, sun-loungers, beach towels

Cozy Beach Cottage

10.0 out of 10, Exceptional, (53)
"This was the perfect property for our visit to Martha’s Vineyard. The owners were so responsive and gave us a seamless experience. I would definitely stay at the Cozy Cottage again! "
Cozy Beach Cottage
Charming newly renovated home in Little Compton.
Fridge, microwave, oven, stovetop

Charming newly renovated home in Little Compton.

10.0 out of 10, Exceptional, (5)
Charming newly renovated home in Little Compton.
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
Interior

Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

2.0 star property
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Property grounds

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

9.8 out of 10, Exceptional, (23)
"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Exterior

Spacious home in central location with beautiful patio, pool table, W/D, & AC

2.0 star property
10.0 out of 10, Exceptional, (3)
"Absolutely loved our stay at this Oak Bluffs home! The location was perfect—just a 20-minute walk to downtown—and the house itself was warm, inviting, and beautifully laid out with an open-air feel. The kitchen was fully stocked, the beds were super comfortable, and the outdoor shower was a wonderful bonus. We felt completely relaxed and free during our stay. Can’t wait to come back next summer!"
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!
On the beach

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

10.0 out of 10, Exceptional, (62)
"The most magical place, thank you for the prefect stay."
Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Beach nearby, sun-loungers, beach towels

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

9.6 out of 10, Exceptional, (31)
"This home was absolutely beautiful. In a great location to get anywhere in the island. The host was extremely helpful when needed. I would one hundred percent recommend this place to anybody! "
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Property grounds

Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

9.8 out of 10, Exceptional, (78)
"Central property with all essentials!"
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Terrace/patio

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

10.0 out of 10, Exceptional, (27)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Oceanview 2 Double Bed Groundfloor Suite
Beach nearby

Oceanview 2 Double Bed Groundfloor Suite

6.0 out of 10, (2)
"Our trip was a last minute decision, and needed to stay just one night. The location, the fast response, clear instructions, cleanliness, assigned parking and pricing all came together very nicely! "
The price is €177
includes taxes & fees
22 Sept - 23 Sept
Oceanview 2 Double Bed Groundfloor Suite
Cozy getaway in a central location w/ a full kitchen & furnished deck
Beach

Cozy getaway in a central location w/ a full kitchen & furnished deck

6.8 out of 10, (23)
"The furniture and amenities provided were good"
Cozy getaway in a central location w/ a full kitchen & furnished deck
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Exterior

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (62)
"The home was wonderful, such a treasure. Great for family and friends. Large kitchen provides ample room for entertaining, all the supplies you need. Hope to be able to go back."
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Dining

THE PARK ESTATE! Your Martha's Vineyard Getaway!

9.8 out of 10, Exceptional, (17)
"The Park Estate is absolutely a phenomenal property. This estate has EVERYTHING you could ever want and need! The estate is well appointed, wonderfully located to travel throughout the area and the host, grounds keeper and everyone we communicated with was so kind, accessible and very informative. How we were so blessed to be able to rent this beautiful property at the last minute. It truly was fate. We look forward to future opportunities to stay here!"
THE PARK ESTATE! Your Martha's Vineyard Getaway!
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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Top Cuttyhunk Hotel Reviews

Newport Beach Hotel & Suites

Newport Beach Hotel & Suites

10/10 Excellent
"Clean, comfortable beds, nice people and great continental breakfast "
Orville 1-night trip
Posted 3 days ago
Newport Beach Hotel & Suites

Find out more about Cuttyhunk

Find out more about Cuttyhunk

Everything you need to know about Cuttyhunk holiday rentals

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

Cuttyhunk holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cuttyhunk holiday rentals we have selected for you start as low as €168 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 holiday 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 holiday.

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.