Cuttyhunk Holiday Rentals

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Holiday Rentals in Cuttyhunk

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (187)
"Great location and helpful staff"
United States
Susan
InnSeason Resorts Captain's Quarters
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
9.8 out of 10, Exceptional, (161)
"Great place, loved it! Had everything we needed."
United States
Michelle P.
The price is AU$278
includes taxes & fees
20 Oct - 21 Oct
Dog Friendly Cottages w/ easy access to Newport, beaches, trails and vineyards
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
6.4 out of 10, (31)
"The weather was perfect and our crew made the best of our trip."
United States
Lisa S.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Cozy getaway in a central location w/ a full kitchen & furnished deck
6.6 out of 10, (24)
"The furniture and amenities provided were good"
United States
Joseph T.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
8.8 out of 10, Excellent, (33)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
United States
Maryann B.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
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."
United States
Swathanthra M.
The price is AU$1,886
includes taxes & fees
20 Oct - 21 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Beachside Village Resort
3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
United States
Kristin
Beachside Village Resort
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."
United States
Matthew
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
Ground-Floor Studio w/ 2 King Beds & Kitchenette (103)
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! "
United States
Arpi L.
The price is AU$265
includes taxes & fees
20 Oct - 21 Oct
Ground-Floor Studio w/ 2 King Beds & Kitchenette (103)
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View
10.0 out of 10, Exceptional, (168)
"Fantastic beach house. Thoughtfully stocked with everything you may need. Great location and convenient to all beaches and Newport. We highly recommend a stay at this beautiful spot."
United States
Sally C.
Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
10.0 out of 10, Exceptional, (71)
"Large home with plenty of room for extended family. Located in quiet neighborhood close to Oak Bluffs, would highly recommend."
United States
Eileen P.
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
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."
United States
Molly L.
Walk to beach! Great large outdoor patio. Still booking fall 2025!
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
10.0 out of 10, Exceptional, (104)
"Great spot "
United States
Cole M.
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
10.0 out of 10, Exceptional, (52)
"Beautiful home in a great location! "
United States
Maurice R.
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
Spacious colonial home close to town with AC, porches, & W/D
9.4 out of 10, Exceptional, (6)
"We had such a great stay here. Very clean and super close to town. We would definitely stay here again. Thanks!"
United States
William C.
Spacious colonial home close to town with AC, porches, & W/D
Private Spacious Pet Friendly Studio / Loft
10.0 out of 10, Exceptional, (79)
"Everything was perfect. It was the cutest place hosted by the nicest people. I wish we didn’t live so far because we were truly so sad when we had to leave!"
United States
Sarah A.
Private Spacious Pet Friendly Studio / Loft
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
8.0 out of 10, Very good, (17)
"Well maintained. Very quiet. No TV. Doubt if there is any air conditioning. "
United States
Joseph
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
Charming newly renovated home in Little Compton.
10.0 out of 10, Exceptional, (6)
Charming newly renovated home in Little Compton.
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
10.0 out of 10, Exceptional, (7)
"Excellent property with a wonderful pool and quiet neighborhood. Listing was accurate as described and communication with owner was prompt and helpful to all questions. Excellent amenities including game room with pool table and boats games. Great location for adults and children to enjoy. "
United States
John Y.
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
9.6 out of 10, Exceptional, (58)
"Loved the house, perfect location. Very well kept it was our second time staying at this house and we will be back"
United States
Robert R.
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
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

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, 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 favourite 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 depend 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 AU$265 per night. Entering your travel dates in the search wizard might find you 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.