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Cutchogue vacation rentals

We found 1,055 vacation rentals — enter your dates for availability

Discover a selection of 42 homes and other vacation rentals in Cutchogue that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Cutchogue

Showing deals for:Jun 26 - Jul 3

Image gallery for Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

9% off
Price is $1,599
$11,196 for 7 nights
All fees included
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

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Find out more about Cutchogue

Why visit Cutchogue

  • Scenic Beaches: Enjoy the stunning beaches of Cutchogue, perfect for sunbathing and relaxation.
  • Cultural Experiences: Visit fascinating museums and explore the rich history of the area.
  • Outdoor Adventures: Engage in various outdoor activities, from hiking to water sports.
  • Charming Accommodations: Choose from cozy cottages and private homes for a unique stay.
  • Family-Friendly Atmosphere: Experience a welcoming environment ideal for both families and couples.

Popular types of accommodation in Cutchogue

Planning a getaway to Cutchogue? The next step is finding the perfect place to unwind. Explore an exciting array of vacation rentals, including private homes, charming cottages, and cozy apartments. Whether you're searching for the best house rentals or top options in Cutchogue, you'll discover accommodations that offer comfort, convenience, and local charm. Your ideal vacation home awaits.

  • Houses: These spacious and comfortable homes are the top choice for visitors seeking a home-like atmosphere during their stay in Cutchogue.
  • Cottages: Charming and cozy, cottages offer a quaint retreat, perfect for couples or small families wanting a peaceful getaway.
  • Apartments: Ideal for those looking for convenience, apartments provide a great mix of comfort and accessibility in the heart of Cutchogue.
  • Villas: For a touch of luxury, villas boast elegant amenities and ample space, making them a favored option for larger groups.
  • Cabins: Rustic and inviting, cabins are perfect for nature lovers wanting to immerse themselves in Cutchogue’s scenic surroundings.**

Top attractions in and around Cutchogue

Cutchogue, New York, is the perfect destination for a romantic getaway or an outdoor adventure. With stunning beaches, fascinating museums, and beautiful urban parks, there's something for everyone. Whether you're seeking cultural experiences or just want to relax by the water, Cutchogue offers a blend of entertainment and natural beauty that will make your vacation unforgettable.

  • The Hamptons Beaches: Located 8 miles from Cutchogue, this stunning beach offers a quintessential coastal experience with soft sands and refreshing ocean waves, perfect for sunbathing and swimming.
  • Harbes Family Farm: Just 5 miles away, this family-friendly farm features interactive activities like berry picking, hayrides, and seasonal festivals, making it a great spot for visitors of all ages.
  • 8 Hands Farm: Situated in Cutchogue, this public art space showcases local culture and creativity, providing a unique atmosphere that blends artistry with community engagement.

Things to do recommended for couples

For a romantic getaway in Cutchogue, visit Pindar Vineyards for wine tasting and charming vibes. Try your hand at mini-golf at Shelter Island Whale's Tail for some fun. For the adventurous couple, the Long Island Skydiving Center offers thrilling views and unforgettable experiences.

Things to do recommended for families

Your family will love the fun at Splish Splash Water Park, just 14 miles away, with thrilling water rides. Enjoy relaxation at Goldsmith's Inlet Park, 3 miles from Cutchogue, or take a spin on the charming Greenport Carousel, located 9 miles away, perfect for outdoor family fun.

Things to do recommended for groups

Groups visiting Cutchogue can enjoy a round of golf at Shinnecock Hills or Sebonack Golf Course for outdoor fun. For a cultural experience, catch a performance at the nearby Bay Street Theatre, perfect for entertainment and family bonding.

*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 Cutchogue

When planning your trip—be it with friends, family, pets, or for an extended stay—it's essential to prioritize your preferences during your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cutchogue with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group activities. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Cutchogue with young kids: Traveling with young kids can be tough. It’s important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions for a more enjoyable experience.
  • Taking your pets with you to Cutchogue: For many families, a vacation wouldn’t be the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Cutchogue: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Cutchogue

Cutchogue, New York, offers a delightful blend of romance and relaxation, making it the ideal getaway for families and couples alike. With its charming family homes and scenic surroundings, visitors can explore nearby areas while enjoying the vibrant atmosphere. Whether you're indulging in outdoor adventures or savoring local entertainment, summer in Cutchogue promises a memorable experience filled with friendly faces and rich history. Discover the perfect escape in this beautiful region of Long Island.

  • Hamptons: Located 9 miles from Cutchogue, the Hamptons are a quintessential summer escape known for their stunning beaches and vibrant outdoor scene. Visitors can indulge in various activities, from relaxing on the sandy shores to enjoying a round of golf at one of the many prestigious courses. The area is also famous for music concerts and luxurious resorts, making it a popular romantic getaway. Local landmarks include picturesque family beaches and serene lakes, perfect for a day of fun in the sun.
  • Southampton: Situated 10 miles away from Cutchogue, Southampton is a charming city that combines beachside relaxation with outdoor adventures. This destination attracts visitors seeking romantic experiences and family-friendly activities alike. Golf enthusiasts can tee off at various golf courses, while winter sports lovers can hit the nearby ski fields. The city’s inviting beaches and beautiful lakes offer plenty of opportunities for water activities and picnics, making it a delightful spot to explore.
  • Greenport: Just 9 miles from Cutchogue, Greenport is a picturesque waterfront city that promises a blend of outdoor excitement and romantic ambiance. Visitors can experience live music concerts or unwind at local resorts, all while surrounded by breathtaking natural beauty. The area’s beaches and family-friendly shorelines are perfect for a day out, and its event conference venues often host various community gatherings and celebrations, making Greenport a vibrant place to discover.

Best time to go to Cutchogue

If you're planning a trip to Cutchogue, 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 February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyModerately LowModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately HighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy-to-use platform for planning your journeys. You can start new trip ideas, continue from where you last stopped, or neatly arrange your travel plans. Your saved or booked properties will be organized into sections for Potential, Upcoming, or Current Trips. To explore the benefits of Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Cutchogue getaway

Learn about the unique charm of Cutchogue with a stay in a private vacation home. There's no shortage of things to see and do in the area.Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Cutchogue

Are you looking for attractions to visit while you're in town? Venture out of your vacation home and experience everything that Cutchogue has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Peconic Bay Winery (0.6 mi / 1 km)
  • Bedell Cellars (1.5 mi / 2.5 km)
  • Pindar Vineyards (1.8 mi / 2.9 km)
  • Raphael Winery (2.1 mi / 3.4 km)
  • Macari Vineyards (4.6 mi / 7.4 km)
  • Martha Clara Vineyards (5.8 mi / 9.3 km)

Exploring the natural landscape of Cutchogue

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Cutchogue. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Sunset Beach (7.6 mi / 12.2 km)
  • Foster Memorial Town Beach (8.4 mi / 13.5 km)
  • 67 Steps Beach (9.7 mi / 15.6 km)
  • Cooper's Beach (11 mi / 17.7 km)
  • The Hamptons Beaches (11.2 mi / 18 km)
  • Shinnecock East County Park (11.5 mi / 18.5 km)

Transportation to and around Cutchogue

The nearest airport is in East Hampton, NY (HTO), located 12.8 mi (20.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Westhampton, NY (FOK-Francis S. Gabreski), which is 14.2 mi (22.9 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Cutchogue?
Prices for vacation rentals in Cutchogue 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 Cutchogue 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 Cutchogue vacation house rentals?
You can find great discounts on house rentals in Cutchogue 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.
Where are the best areas for renting a beach house in Cutchogue?
For renting a beach house in Cutchogue, consider the charming waterfront areas along Long Island's North Fork. The vicinity near Cutchogue Harbor offers picturesque views and easy access to sandy beaches, where visitors can enjoy swimming and sunbathing. Many rental properties in this area come equipped with amenities such as spacious decks for outdoor dining, private docks for boating access, and fully equipped kitchens, making them superb for families or groups seeking a relaxing getaway.

Additionally, the nearby beaches along the Peconic Bay, such as those close to the village center, provide a quaint atmosphere with local shops and eateries within walking distance. Rentals here often feature cozy living spaces, outdoor grills for summer barbecues, and some may even include kayaks or paddleboards for exploring the bay.

For those interested in a more rural experience, heading slightly inland to the vineyards of the North Fork can offer unique vacation rentals in charming wine country settings. Many properties here have large yards, fire pits, and easy access to wine tasting tours, allowing guests to enjoy both the beach and the local wine culture.
What is the most popular type of vacation rental accomodation in Cutchogue?
In Cutchogue, vacation houses are the most popular rental option, with about 26 available throughout the area. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and often outdoor areas for relaxation, making them ideal for families or groups. Additionally, there are several cottages scattered around, which offer a charming and cozy atmosphere, superb for those looking for a more intimate stay.
Are there any family house rentals in Cutchogue?
In Cutchogue, New York, there are some available family-friendly house rentals, with around 27 options throughout the area. This charming town, located on the North Fork of Long Island, offers a delightful blend of rural beauty and coastal attractions, making it a great spot for family gatherings. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces that may include patios or gardens for children to play in.

Visitors can enjoy easy access to nearby beaches, such as those along Long Island Sound, as well as local vineyards and farms that provide opportunities for family-friendly activities like fruit picking and wine tastings for the adults.
Can I rent a vacation home with a pool or hot tub in Cutchogue?
In Cutchogue, there are several vacation homes available for rent that feature pools and hot tubs, with around 10 options to choose from. This charming part of Long Island's North Fork is known for its beautiful vineyards and proximity to the scenic coastline. Many of these properties come equipped with private pools and hot tubs, providing a ideal setting for relaxation after a day of exploring the local wineries or nearby beaches. Travelers can expect amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making these rentals ideal for families or groups looking to enjoy a peaceful getaway.
Can I find long-stay vacation rentals in Cutchogue?
A long-stay vacation rental in Cutchogue 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 pet-friendly house rentals in Cutchogue?
In Cutchogue, there are several pet-friendly house rentals available, offering a great escape in this charming North Fork community. Many of these vacation homes come equipped with amenities such as spacious backyards, outdoor decks, and fully furnished kitchens, providing a comfortable stay for both travelers and their furry companions.

The area is known for its beautiful landscapes and proximity to local attractions, including nearby vineyards and the scenic Cutchogue Harbor, which is superb for leisurely walks. Additionally, the surrounding parks and nature preserves offer opportunities for outdoor activities with pets, making Cutchogue an excellent destination for those traveling with animals. See all pet-friendly rentals in Cutchogue.
Are there any remote work vacation rentals in Cutchogue?
In Cutchogue, New York, there are numerous options for remote work vacation rentals, with around 33 available in the area. This charming North Fork community offers a peaceful setting ideal for those looking to blend work and leisure. Many of these rentals come equipped with essential amenities such as high-speed internet and Wi-Fi access, ensuring a productive work environment.

Travelers can expect spacious rooms that often feature dedicated workspaces, comfortable living areas, and fully equipped kitchens, making it easy to prepare meals during their stay. The serene surroundings provide a great backdrop for outdoor breaks, with local attractions including vineyards, farms, and scenic waterfronts nearby. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cutchogue vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cutchogue 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.
What are popular rental amenities in Cutchogue?
In Cutchogue, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals. Many rentals feature blenders, making it easy to whip up smoothies or other blended drinks. Outdoor spaces such as decks or patios are common, providing guests with a private area to relax and enjoy the serene surroundings. Cozy fireplaces are also a highlight, superb for creating a warm atmosphere during cooler evenings. Additionally, onsite parking is typically available, ensuring convenience for those traveling by car.
When is the best time to visit Cutchogue for a vacation rental?
The best time to visit Cutchogue for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts travelers eager to experience the picturesque vineyards and charming coastal scenery that Cutchogue is known for. With warm temperatures typically ranging from the mid-60s to the mid-80s Fahrenheit, it's an ideal time for outdoor activities such as wine tasting, cycling, and enjoying leisurely walks along the waterfront.

During the summer months, visitors can experience firsthand local festivals, farmers' markets, and the beautiful beaches, making it a lively time for families and friends alike. The inviting atmosphere enhances the experience of exploring the nearby North Fork wineries, which offer tastings and tours that highlight the region's exceptional wine production.

For those looking for a more budget-friendly option, consider visiting in December. While it's the low season, this time offers a unique charm with fewer crowds. Travelers can enjoy cozy stays and the festive spirit of the holiday season, complete with local events and decorations that bring a warm ambiance to the area.

In summary, whether you choose the bustling summer months to soak in all the excitement or opt for a quieter winter retreat, Cutchogue has something special to offer year-round.
How early should I book a Cutchogue vacation rental?
Book your Cutchogue 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 Cutchogue, New York, United States of America?
In Cutchogue, visitors can enjoy a charming array of attractions centered around the area's rich agricultural heritage and scenic beauty. The North Fork Wine Region is a significant draw, with several vineyards and wineries offering tastings and tours. Many vacation rentals in this area provide easy access to these wineries, making it convenient for guests to explore local wines.

The Cutchogue Village Green is another highlight, featuring a picturesque setting with historic buildings and a gazebo, great for leisurely strolls or picnics. Nearby, the Cutchogue Harbor offers opportunities for boating and water activities, allowing visitors to experience the natural beauty of Long Island Sound.

For those interested in history, the Cutchogue New Suffolk Historical Council maintains sites that showcase the area's past, including the historic Cutchogue Schoolhouse. The nearby beaches, such as New Suffolk Beach and beaches along the Peconic Bay, provide lovely spots for sunbathing and swimming.
Can I change or cancel my Cutchogue home rental booking on Vrbo?
To find Cutchogue 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 Cutchogue 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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