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, (186)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters

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

9.8 out of 10, Exceptional, (159)
"Great place, loved it! Had everything we needed."
The price is AU$274
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."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

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."
The price is AU$1,860
includes taxes & fees
12 Oct - 13 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

10.0 out of 10, Exceptional, (64)
"The house was well stocked and had everything you could need. "
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

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

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

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

9.8 out of 10, Exceptional, (80)
"Central property with all essentials!"
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts

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

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! "
The price is AU$262
includes taxes & fees
3 Nov - 4 Nov
Ground-Floor Studio w/ 2 King Beds & Kitchenette (103)

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

NEW MARKDOWN! Stay at a waterside beach cottage minutes away from water!

9.2 out of 10, Wonderful, (31)
"So at home - loved every minute"
NEW MARKDOWN! Stay at a waterside beach cottage minutes away from water!

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
"We had such a great stay here. Very clean and super close to town. We would definitely stay here again. Thanks!"
Spacious colonial home close to town with AC, porches, & W/D

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."
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is AU$1,028
includes taxes & fees
23 Oct - 24 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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."
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"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

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. "
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs

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

10.0 out of 10, Exceptional, (29)
"Perfect for my family of 4. Very walkable to everything Vineyard Haven. "
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette

8.0 out of 10, Very good, (16)
"Well maintained. Very quiet. No TV. Doubt if there is any air conditioning. "
Nana's Backyard Treehouse with deck, electric/gas grills, kitchenette
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

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$262 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.