Cuttyhunk vacation rentals

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Discover a selection of vacation rentals in Cuttyhunk that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, such as WiFi and cable TV. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

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Find the best place to stay - Cuttyhunk

Wander Cuttyhunk Waterfront

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Top rated rentals - Cuttyhunk

Pefect beach stay

This cottage fit my descirption of the perfect beach getawy. The view was beautiful and the location was ideal- close to fishing, SUP/kayaking, walking, biking and swimming. Our family had a relaxing time just enjoying all the thngs we love to do at the beach. The cottage was clean and had everything we needed. The host was extremly attentive and welcomed us with a few goodies. There is really nothing we would have changed. It was exactly what we wanted.

Christina W.

Stayed Aug 2025

Image of Cozy Artist's Cottage by the Sea

Great Westport 2-BR Rental!

Had a great stay at this house in Westport last week. Host is very responsive and very friendly. Property is in a nice location with lots of parking (could easily fit 4 cars). Very clean house. Well-stocked kitchen with large island for food prep and eating. Comfortable living room area with games. Two good-sized bedrooms. Great outdoor shower. Best of all, house is well-appointed with a/c, which was much appreciated by us during the 90-degree weather we had! Our friends were jealous! This was our first time to Westport, and we really enjoyed the area and this rental We'll be looking to rent here again next year!

James N.

Stayed Jun 2025

Image of Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Premier Host

Beautiful Property

My family had an incredible time staying at this house. My two kids (ages 3 and 1.5) loved looking for frogs in the pond and my dog loved running around the large yard. During the day, we went to the beach right down the road and at night, we went out to dinner in a nearby town or ate at home and made s’mores by the fire. I highly recommend if you want to have a perfect vacation.

Sarah P.

Stayed Aug 2024

Image of Magical House in the Trees with Water View - Secluded Area

MVY relaxation

We were there for a family wedding. House was relaxed and plenty of different spaces (it was raining and windy) when we were inside. Loved the kitchen and large table to gather around. Beautiful screened in porch. Good mattresses on all the beds. Everything worked . Loved using the outdoor shower, though the others went for the regular type.

Alya R.

Stayed Sep 2023

Image of Secluded Waterfront - North Shore - Private Beach

Photos don’t do it justice!

This is a cute, clean and well stocked cottage that was just right for our family of 5. There was plenty of space for the kids to play games and do crafts inside, but we spent most of our time outdoors. The private beach lot access was a generous part of the rental perks and saved the somewhat lengthy hike to Moshup Beach from the public parking lot with 3 young children. Without all the beach stuff, we walked to the beach from the cottage, all the way around the cliffs, up to the shops for lunch, toured the lighthouse, then walked to the cottage along the road. Andrew was very responsive with any questions or concerns. The suggestion about purchasing groceries on the way in makes a lot of sense given the remoteness of the location, but we made the trip into town after arriving and it was not a big deal. One thing to note is that the beach below the house is clothing optional, not a huge deal either, but just an unexpected conversation with the kids! We would definitely return!

Michelle M.

Stayed Jul 2023

Image of 'Little Neck' ~ Where The Slocum River Meets Buzzards Bay ~ 7 Acres!

Good friends

Six long-time friends spent a splendid week at the house and not one had a complaint, except that Charlotte's cookies ran out too fast.

Andrew H.

Stayed Jun 2023

Image of Modern House in Aquinnah With Water View from the Rooftop Deck and Beach Access.

Amazing Aquinnah Accommodation!

We spent a fabulous two weeks at this beautiful property. The beach is a short walk (or several others within brief drive), the cliffs and shops are nearby, and the roof deck offers fantastic views. This was a perfect place for our family to enjoy an up-island getaway. The central building offers a large, modern, and well-appointed gathering, cooking, and eating space. The two separate sleeping areas worked perfectly for our group—both spaces felt welcoming and luxurious. Parents/kids shared one building comfortably while grandparents relaxed in their own suite. The hosts also provide—literally—everything you could need to enjoy your stay (high quality beach chairs, towels, cooler, portable Bluetooth speaker, etc.). AC units and ceiling fans keep everyone cool and comfortable in each space. Anyone thinking of booking here should not hesitate (unless it is for weeks we are hoping to return)!

Mark M.

Stayed Jul 2022

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Find out more about Cuttyhunk

Why visit Cuttyhunk

Scenic Waterfront: Enjoy breathtaking views of the Cuttyhunk Channel and Harbor, perfect for relaxation and photography.
Outdoor Activities: Engage in fishing trips, hiking, and beach outings, especially at Charlestown Beach.
Charming Community: Experience the friendly atmosphere and cozy ambiance of this quaint island village.
Vacation Rentals: Choose from a variety of charming cottages and vacation homes for a comfortable stay.
Rich History: Discover the local culture and history through visits to nature preserves and iconic landmarks.

Popular types of accommodation in Cuttyhunk

Cuttyhunk offers a variety of vacation rentals perfect for your getaway. Whether you're looking for houses, charming cottages, or cozy apartments, you'll find the ideal place to stay. Explore the beauty of Cuttyhunk Island with options that cater to every traveler's needs. Discover your perfect Cuttyhunk rental today and enjoy a memorable vacation in this serene destination.

Houses: The top choice for visitors, these homes offer spacious and comfortable accommodations ideal for families, groups, or couples seeking privacy and convenience.
Cottages: A charming option, cottages provide a quaint and cozy atmosphere, perfect for a relaxing getaway close to nature.
Apartments: These versatile spaces are great for those who prefer a home-like environment with easy access to local amenities.
Condos: Offering modern comforts and often located in desirable areas, condos are a popular choice for vacationers.
Villas: Luxurious and spacious, villas provide an upscale experience for travelers looking for a lavish retreat.**

Top attractions near Cuttyhunk

Cuttyhunk, Massachusetts, is a perfect destination for outdoor and beach enthusiasts. Visitors can enjoy the scenic Cuttyhunk waterfront, explore the island, and take in views of the Cuttyhunk Channel and Harbor. Popular activities include fishing trips and visiting local points of interest like the ferry terminal and nature preserves, making it an ideal spot for travelers seeking culture and adventure in a beautiful coastal setting.

Woods Hole Ferry Terminal: A bustling hub for travelers, this terminal offers scenic ferry rides to Martha's Vineyard and Nantucket, showcasing stunning ocean views. The area is rich in maritime history and features charming shops and eateries.
Gay Head Lighthouse: A historic landmark perched on the cliffs of Aquinnah, this lighthouse provides a glimpse into the region's maritime heritage. Enjoy breathtaking coastal views and explore the surrounding colorful clay cliffs.
Horseneck State Beach: A beautiful stretch of sandy beach perfect for sunbathing, swimming, and beachcombing. Its tranquil atmosphere and scenic dunes make it an ideal spot for relaxation and enjoying nature.

Things to do recommended for couples

Cuttyhunk offers a charming escape for couples. Explore the scenic beaches, take a sunset sail around the island, or enjoy a cozy dinner at a local seafood restaurant. Don't miss a leisurely walk along the shoreline, soaking in the breathtaking views and creating unforgettable memories together.

Things to do recommended for families

Families will love exploring the scenic beaches of Cuttyhunk, where kids can enjoy tide pooling and sandcastle building. Don't miss the chance to hike the island's trails for stunning views, or take a boat tour to spot local wildlife and enjoy the serene waters.

Things to do recommended for groups

Explore the serene beaches and enjoy group kayaking around Cuttyhunk Island. Gather your friends for a scenic hike on the trails or embark on a fishing charter for a day of fun on the water. Don't miss the stunning sunsets perfect for group photos.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Cuttyhunk

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

Traveling to Cuttyhunk with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for these options and many more on Vrbo.
Traveling to Cuttyhunk with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
Taking your pets with you to Cuttyhunk: For many families, a vacation wouldn’t be the same without their furry companions. If you relate to this, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Cuttyhunk: If you're seeking vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in Cuttyhunk

Cuttyhunk, a charming island village in Massachusetts, offers a serene escape perfect for outdoor enthusiasts and beach lovers. Explore the cozy ambiance and friendly atmosphere as you unwind on Charlestown Beach or in spacious vacation homes. With a blend of relaxation and rich history, this destination invites families and budget travelers alike to experience its scenic beauty and welcoming community. Discover the best of island life as you create unforgettable memories in this hidden gem.

Martha's Vineyard: Located approximately 15 miles from Cuttyhunk, Martha's Vineyard is a picturesque island known for its stunning beaches and charming communities. Visitors flock to the island for its incredible outdoor experiences, breathtaking scenery, and laid-back atmosphere. Enjoy a day at iconic beaches, participate in water sports, or explore the quaint streets filled with artisanal shops and restaurants. The island is also home to vibrant music concerts and luxurious resorts, making it an ideal destination for relaxation and entertainment. Don't miss the chance to visit landmarks such as the beautiful Cape Poge Lighthouse and the family-friendly beaches that provide fun for all ages.
Gosnold: As the town that encompasses Cuttyhunk, Gosnold offers a unique blend of outdoor adventure and serene landscapes. This small town is perfect for travelers seeking a romantic getaway or an opportunity to connect with nature. Here, you can enjoy scenic hikes along the coastline, relax at the local beaches, or explore nearby lakes. Gosnold also features cultural experiences, including local music concerts and educational activities that provide insight into the area's rich history. Its intimate setting makes it a peaceful escape for couples and families alike.
Elizabeth Islands: Just 8 miles from Cuttyhunk, the Elizabeth Islands are an archipelago offering a serene retreat for nature lovers and outdoor enthusiasts. These islands are known for their stunning scenery, beautiful beaches, and recreational opportunities. Visitors can indulge in a variety of activities such as water sports, beachcombing, and hiking through scenic trails. The islands also feature ski lifts and fields for those who enjoy winter sports. With breathtaking views of the coastline and tranquil lakes, the Elizabeth Islands are a perfect spot for a relaxing day trip or an adventurous getaway.

Best time to go to Cuttyhunk

If you're planning a trip to Cuttyhunk, Gosnold, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.2°F (1.8°C)	Light Rain	Mostly Sunny	Low	Moderately Low
February	35.2°F (1.8°C)	Light Rain	Mostly Sunny	Low	Moderately Low
March	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Low	Moderately Low
April	46.4°F (8.0°C)	Light Rain	Mostly Sunny	Average	Average
May	54.5°F (12.5°C)	Light Rain	Mostly Sunny	Average	Average
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	High	Moderately High
July	71.1°F (21.7°C)	Light Rain	Mostly Sunny	High	Moderately High
August	71.8°F (22.1°C)	Light Rain	Mostly Sunny	High	Moderately High
September	66.7°F (19.3°C)	Light Rain	Mostly Sunny	Average	Average
October	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Average	Average
November	49.1°F (9.5°C)	Light Rain	Mostly Sunny	Average	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Average	Average

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Additionally, extending your stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform where you can create new trips, continue your planning from where you left off, or manage your existing travel arrangements. You’ll see your saved or booked properties neatly organized into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting tranquil Cuttyhunk

Enjoy the history and other features of Cuttyhunk. This relaxing city is known for its kayaking, fishing and island views. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Cuttyhunk

Do you want to find attractions to see in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Cuttyhunk a one-of-a-kind vacation spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Coastal Vineyards (10.2 mi / 16.4 km)
Westport Rivers Vineyard & Winery (12.4 mi / 19.9 km)
Buttonwood Park Zoo (14.4 mi / 23.2 km)
Carolyn's Saskonnet Vineyard (15.5 mi / 24.9 km)
Acoaxet Club (13.7 mi / 22 km)
Chilmark Chocolates (11 mi / 17.7 km)

Exploring the natural features in Cuttyhunk

Whether you're an active traveler or just want to appreciate the scenery, Cuttyhunk is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

Aquinnah Cliffs (7 mi / 11.3 km)
Horseneck State Beach (8.8 mi / 14.2 km)
Menemsha Beach (9.6 mi / 15.5 km)
Slocum's River Reserve (9.9 mi / 15.9 km)
Goosewing Beach Preserve (11.8 mi / 18.9 km)
Tappens Beach (13.1 mi / 21 km)

How to get to and around Cuttyhunk

Fly into Vineyard Haven, MA (MVY-Martha's Vineyard), the closest airport, located 16.6 mi (26.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to New Bedford, MA (EWB-New Bedford Regional), which is 17.4 mi (28.1 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Cuttyhunk?

Prices for vacation rentals in Cuttyhunk vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cuttyhunk to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for Cuttyhunk vacation house rentals?

You can find great discounts on house rentals in Cuttyhunk on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay vacation rentals in Cuttyhunk?

A long-stay vacation rental in Cuttyhunk is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Are there any Cuttyhunk vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Cuttyhunk with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

How early should I book a Cuttyhunk vacation rental?

Book your Cuttyhunk vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in Cuttyhunk, Massachusetts, United States of America?

In Cuttyhunk, visitors can enjoy a serene and picturesque environment with a range of attractions that highlight the island's natural beauty. The Cuttyhunk Island Wildlife Refuge is a key point of interest, offering opportunities for birdwatching and hiking along scenic trails. The island's beaches, such as Cuttyhunk Harbor and the more secluded areas along the shoreline, provide superb spots for swimming, sunbathing, and picnicking.

The historic Cuttyhunk Lighthouse, located at the northern tip of the island, is another must-see, offering stunning views of the surrounding waters and a glimpse into the maritime history of the area. Additionally, the local fishing community provides an authentic experience with chances to partake in fishing excursions, or simply enjoy fresh seafood at local eateries.

Can I change or cancel my Cuttyhunk home rental booking on Vrbo?

To find Cuttyhunk vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

Are all fees included in the Cuttyhunk vacation rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

What is VrboCare™ and how does it work?

Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.

What can I expect from Vrbo customer service and VrboCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.

Can I plan a group trip on Vrbo?

Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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