Cuttyhunk Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Cuttyhunk

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

West Tisbury
9.0 out of 10, Wonderful, (35)
"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

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

Oak Bluffs
6.6 out of 10, (25)
"The home was nice, a little outdated, but great for a family. Unfortunately it does not have AC and when we arrived we found 2 fans were broken. We immediately contacted Vacasa who said they would send maintenance. While waiting for maintenance, we also noticed within the first hour that one of the dining chair backs was broken/not attached, one of the bed posts fell off as it was not attached, and the fan in one of the bathrooms was stuck on. We planned to notify maintenance when they came but...
United States
Dawn R.
Cozy getaway in a central location w/ a full kitchen & furnished deck

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

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Beachside Village Resort

3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort

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

Middletown
10.0 out of 10, Exceptional, (107)
"The property was amazing and the host was so easy to communicate with! We love to the location and would definitely stay again"
United States
Kayla Z.
Recent Construction, Fire Pit, Kayaks, Close to Town, and Beach. Easton’s Point.

Stones Throw Waterfront

Dartmouth
8.8 out of 10, Excellent, (6)
"According to the listing, the property has AC. That is not true. It had a tiny portable unit that wasn't on when we entered and didn't cool once it was turned on. It also had a window unit that had no place to plug in. There were bugs in multiple areas. The property was not habitable, so we ended up booking a hotel room in a nearby town. VRBO compensated us partially but the owner was unwilling to refund any of our money even though we did not stay in the property. "
United States
Ashley R.
The price is NZ$1,126
includes taxes & fees
26 Nov - 27 Nov
Stones Throw Waterfront

Charming newly renovated home in Little Compton.

Little Compton
10.0 out of 10, Exceptional, (6)
"This house is an absolute gem – a perfect blend of old New England charm but completely newly renovated. Pamela has thought of everything that a guest could need to make your stay comfortable and relaxed. The house is sparkling clean with spacious bedrooms, beautiful bathrooms, a fully stocked kitchen and lots of room for a family to spread out and enjoy your time in the lovely town of Little Compton. We also appreciated that it is equidistant to points in Westport and Tiverton, which made for...
United States
Sarah C.
Charming newly renovated home in Little Compton.

Seapowet suite

Tiverton
9.6 out of 10, Exceptional, (5)
"Adequate for one night. Host friendly."
United States
Louise
The price is NZ$333
includes taxes & fees
26 Nov - 27 Nov
Seapowet suite

Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

2.0 star property
Falmouth
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

Gorgeous Spacious Victorian Cape Cod Beach View Retreat

Falmouth
10.0 out of 10, Exceptional, (16)
"The house is a wonderful place for a slow and relaxing holiday! Close to everything but tucked away from anything too busy. "
United States
Alexandra M.
Gorgeous Spacious Victorian Cape Cod Beach View Retreat

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is NZ$2,143
includes taxes & fees
14 Nov - 15 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Be on the Beach! Awesome Oceanfront Living Close to Downtown Dining Amazing View

Easton's Point
10.0 out of 10, Exceptional, (170)
"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

Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master

Middletown
10.0 out of 10, Exceptional, (126)
"Great beach house for families!"
United States
Joanne M.
Walk to beach, Huge deck off spacious new kitchen, roof-deck, king master

Cape Cod Cottage Retreat - Close to Beaches, Bike Paths & Downtown Shops!

Falmouth
Cape Cod Cottage Retreat - Close to Beaches, Bike Paths & Downtown Shops!

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

Falmouth
9.8 out of 10, Exceptional, (23)
"Amazing place. Definitely steps from the beach . Also the walk into town was not bad at all. we enjoyed doing that. The house was spacious and clean. Communications were great with the owner Joe. We really enjoyed our stay there. highly recommend the place."
United States
Anonymous traveller
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

Private Spacious Pet Friendly Studio / Loft

Little Compton
10.0 out of 10, Exceptional, (79)
"Easy checkin and very comfortable - nice, friendly hoats"
United States
Susan T.
Private Spacious Pet Friendly Studio / Loft

Middletown Bungalow - RIBryan Property

Middletown
9.4 out of 10, Exceptional, (13)
"Very clean and roomy for our 8 guests. Perfect location for access to Second Beach and downtown Newport."
United States
William H.
The price is NZ$1,132
includes taxes & fees
17 Nov - 18 Nov
Middletown Bungalow - RIBryan Property

Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island

Tiverton
10.0 out of 10, Exceptional, (185)
"This is the fifth year that I’ve rented this place and I love it. It’s very private simple all on one floor."
United States
Debbie I.
Quaint Cottage On Christmas Tree Farm in SE coastal Rhode Island

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

Oak Bluffs
10.0 out of 10, Exceptional, (5)
"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!"
United States
Monica D.
Spacious home in central location with beautiful patio, pool table, W/D, & AC

Newport - Exclusive Renfrew Park Beach House Waterview Apartment, Central A/C

Middletown
9.8 out of 10, Exceptional, (164)
"Return visitor as I knew Deborah goes above and beyond in hospitality. Beautiful home, immaculate and easy drive to beaches, restaurants, and the Bellevue Ave mansions. We’ll be back!"
United States
Anonymous traveller
Newport - Exclusive Renfrew Park Beach House Waterview Apartment, Central A/C
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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 NZ$333 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. 

Frequently asked questions

Can I find a holiday rental in Cuttyhunk?

Yes, there are holiday rentals close to the most popular sights in Cuttyhunk, or you can select a more secluded option if you're looking for a relaxing stay. Cuttyhunk is known for its beaches.

What are some of the best holiday rentals that Cuttyhunk has to offer?

Cozy getaway in a central location w/ a full kitchen & furnished deck: This holiday home rental outside of Cuttyhunk offers a patio, a garden and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 Gooseberry Island are a couple of places you'll find in the wider area.

What’s a holiday rental in Cuttyhunk like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cuttyhunk. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.