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Cutchogue vacation rentals

We found 1,078 vacation rentals — enter your dates for availability

Discover a selection of 45 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:Feb 20 - Feb 27

Image gallery for Lovely Cottage in the Heart of Long Island Wine country

Lovely pond front cottage on the North Fork.
9.8 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold, NY

10% off
Price is CA $347
CA $3,157 total
includes taxes & fees
Lovely Cottage in the Heart of Long Island Wine country

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Find out more about Cutchogue

Why visit Cutchogue

  • Beautiful Beaches: Enjoy the stunning local beaches, perfect for relaxation and summer activities.
  • Cultural Exploration: Delve into local history at museums that showcase Cutchogue's rich heritage.
  • Outdoor Adventures: Experience an array of outdoor activities in the picturesque natural surroundings.
  • Charming Accommodations: Choose from cozy cottages to spacious homes tailored for your vacation needs.
  • Friendly Atmosphere: Immerse yourself in the welcoming community, ideal for couples and families alike.

Popular types of accommodation in Cutchogue

Discover the charm of Cutchogue with a variety of vacation rentals tailored to your needs. Whether you prefer a cozy cottage, a spacious private vacation home, or a convenient apartment, Cutchogue offers an array of options for your stay. Explore our listings for rentals in Cutchogue and find the perfect home rental that suits your travel plans. Experience transparency, savings, and peace of mind with our customer-centric platform.

  • Houses: The top choice for visitors to Cutchogue, these spacious homes offer comfort and privacy, ideal for families or groups.
  • Cottages: A close second, charming cottages provide a quaint and cozy atmosphere, perfect for a peaceful getaway.
  • Apartments: Third on the list, apartments offer a practical and convenient option for those looking for easy access to local attractions.
  • Villas: These luxurious properties rank fourth, offering upscale amenities and stunning views for a more indulgent stay.
  • Cabins: Rounding out the list, cabins provide a rustic escape, ideal for nature enthusiasts seeking tranquility.**

Top attractions in and around Cutchogue

Cutchogue, New York, offers a delightful blend of romantic and outdoor experiences perfect for your vacation. Explore the beautiful beaches, delve into local history at museums, or relax in urban parks. Whether you're seeking cultural enrichment or outdoor adventures, Cutchogue's attractions cater to every traveller's interests, making it an ideal destination for couples and outdoor enthusiasts alike.

  • The Hamptons Beaches: Experience the quintessential beach vibes at The Hamptons Beaches, located 12.9km from Cutchogue. Relax on sandy shores, soak up the sun, and enjoy picturesque ocean views.
  • Harbes Family Farm: Just 8.0km away, Harbes Family Farm offers a delightful family-friendly experience with seasonal activities, fresh produce, and fun farm events, perfect for a day out.
  • 8 Hands Farm: Situated in Cutchogue, 8 Hands Farm showcases local public art and cultural experiences, blending urban creativity with the charm of rural life.

Things to do recommended for couples

For a romantic getaway in Cutchogue, indulge in wine tasting at Pindar or Lenz Vineyards, both just 3.2km away, offering enchanting atmospheres. For a bit of fun, head to Shelter Island Whale's Tail mini golf, located 14.5km away, where you can enjoy a playful adventure together.

Things to do recommended for families

Your family vacation in Cutchogue promises excitement at Splish Splash Water Park, only 22.5km away. Enjoy relaxation at Goldsmith's Inlet Park, just 4.8km away, and take a spin on the charming Greenport Carousel, located 14.5km from your base. Fun awaits everyone.

Things to do recommended for groups

In Cutchogue, groups can enjoy a round of golf at the nearby Shinnecock Hills or Sebonack Golf Courses, both offering beautiful outdoor settings. For a cultural experience, catch a show at 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

If you're traveling with a group, as a family, bringing your pets along, or planning an extended stay, it's important to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Cutchogue with a group: Think about how many bedrooms you’ll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Cutchogue 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 suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cutchogue: For many families, a trip isn't truly fulfilling unless their furry companion is included. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of your family feels right at home.
  • Planning for a long term stay visiting Cutchogue: If you're seeking vacation rentals with discounts 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 a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Cutchogue

Cutchogue, New York, offers a charming getaway perfect for romantic and outdoor enthusiasts. This picturesque town features beautiful local beaches and unique attractions that capture the essence of summer. Enjoy seasonal activities, explore scenic spots, and immerse yourself in the friendly atmosphere. Nearby, you’ll find delightful neighborhoods rich in history and family-friendly experiences, making it an ideal destination for all types of travellers seeking a relaxing escape.

  • Hamptons: Situated 14.5km from Cutchogue, the Hamptons is a premier destination known for its stunning beaches and outdoor activities. Visitors are drawn to its romantic atmosphere, perfect for couples seeking a getaway. Enjoy a round of golf at one of the nearby courses, attend a lively music concert, or relax at a luxurious resort. With beautiful local landmarks including picturesque family beaches and serene lakes, the Hamptons offers a quintessential seaside experience that is both relaxing and invigorating.
  • Southampton: Located 16.1km from Cutchogue, Southampton is a charming city that combines scenic beauty with outdoor adventure. Known for its romantic beaches and lush landscapes, it’s an ideal spot for couples and families alike. Engage in activities such as golfing, skiing, or simply soaking up the sun at the local beaches, which are perfect for family outings. The proximity of lakes adds to the allure, making Southampton a delightful retreat for nature lovers and those seeking a tranquil escape.
  • Greenport: Just 14.5km from Cutchogue, Greenport is a vibrant city offering a blend of outdoor experiences and romantic settings. This charming destination is perfect for those looking to explore golf courses, attend music concerts, or unwind at a local resort. With attractions like family-friendly beaches and event venues, Greenport ensures a memorable visit. Its scenic waterfront and quaint atmosphere make it an excellent choice for a leisurely day trip or a romantic evening stroll.

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 a breeze

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can help, as prices often vary. Additionally, opting for a longer stay typically 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: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last left off, or organize your travel arrangements. You'll discover your saved or booked properties neatly organized under Potential, Upcoming, or Current Trips. To begin making the most of Trip Boards, simply visit: https://www.vrbo.com/en-ca/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)
  • Jamesport Vineyards (7.3 mi / 11.7 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)
  • 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)
  • Ponquogue Beach (12.1 mi / 19.5 km)
  • Sandbar Beach (13.1 mi / 21.1 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

What is the best area to stay in Cutchogue when booking a vacation rental?
When considering a vacation rental in Cutchogue, New York, a popular area to stay is along the scenic Route 25, which runs through the heart of the North Fork. This charming stretch is dotted with vineyards, offering a delightful experience for wine enthusiasts. Staying near this route provides convenient access to popular attractions such as the Cutchogue Village Green and the local wineries, including the renowned Bedell Cellars and Corey Creek Vineyard, both of which offer tastings and beautiful grounds to explore.

Another appealing area is near Cutchogue's picturesque waterfront. This location not only offers stunning views of the bay but also proximity to lovely beaches, such as Cutchogue Village Beach, where visitors can enjoy sunbathing and swimming in the summer months. The waterfront area typically features a selection of vacation rentals that provide a serene atmosphere, great for relaxation after a day of exploring.
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 travelling 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.
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, New York, the area along the North Fork of Long Island is a fantastic choice. The coastline near Cutchogue offers a range of properties with stunning views of the Peconic Bay. Many beach houses in this charming region come with amenities such as private decks, outdoor dining areas, and spacious backyards, ideal for family gatherings or relaxing after a day at the beach.

Particularly, the shoreline near Cutchogue's public beaches, such as those close to the Cutchogue Park District, provides easy access to sandy shores and swimming spots. Rentals here often feature modern kitchens for self-catering, along with comfortable living rooms where guests can unwind in the evenings.

In addition, the nearby town of Mattituck adds to the appeal, with its various shops, restaurants, and local wineries, making it convenient for travellers looking to explore the local culture. Many properties in this area also offer amenities like outdoor showers, which are great for rinsing off after a day spent enjoying the sun and surf.
What is the most popular type of vacation rental accomodation in Cutchogue?
In Cutchogue, vacation houses are the most popular type of rental accommodation, with around 31 available throughout the area. These properties are typically situated in charming neighbourhoods, offering a homely atmosphere ideal for families or groups. Most vacation houses feature spacious layouts, fully equipped kitchens, and outdoor spaces such as patios or gardens, superb for enjoying the pleasant surroundings. Additionally, there are several cottages available, which provide a quaint and cosy option for travellers seeking a more intimate stay.
Are there any family house rentals in Cutchogue?
In Cutchogue, New York, there is a great selection of family-friendly homes—approximately 33 available throughout the area. This charming locale, situated on the North Fork of Long Island, is renowned for its picturesque vineyards and proximity to beautiful beaches, making it a delightful destination for families.

Properties typically boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play. Many rentals also feature amenities such as Wi-Fi, air conditioning, and barbecue facilities, ensuring a comfortable stay for all guests.
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 or hot tubs, with around 14 options to choose from. This charming village, located on Long Island's North Fork, is known for its picturesque vineyards and coastal scenery. Many of these properties come equipped with private pools, outdoor hot tubs, and spacious backyards, making them ideal for relaxation and family gatherings.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Cutchogue?
In Cutchogue, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with furry companions. Many of these vacation rentals come equipped with essential amenities such as spacious kitchens, comfortable living areas, and outdoor spaces where pets can roam freely.
Are there any remote work vacation rentals in Cutchogue?
In Cutchogue, New York, there are numerous remote work-friendly vacation rentals available, with around 37 options to choose from. This charming area, located in the picturesque North Fork of Long Island, offers a tranquil setting with easy access to beautiful vineyards and scenic beaches. Many of the properties are equipped with dedicated workspaces, including desks and ergonomic chairs, as well as high-speed Wi-Fi, making it convenient for those who need to balance work and leisure. 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 travellers 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, allowing guests to prepare their own meals. Most rentals feature essentials such as microwaves, dishwashers, and stovetops, alongside cookware and utensils, ensuring a convenient cooking experience. These amenities cater to travellers looking for a cozy feel while exploring the charming surroundings of this picturesque area.
When is the best time to visit Cutchogue for a vacation rental?
July is the most popular time to visit Cutchogue, making it an ideal month for travellers seeking a vibrant summer experience. During this peak season, from June to August, visitors can experience firsthand the picturesque beauty of the North Fork, where charming vineyards and inviting beaches beckon. With average temperatures around the mid-20s Celsius, the warm weather creates superb conditions for outdoor activities and leisurely strolls through the scenic countryside.

If you're keen on exploring the local wineries or indulging in fresh farm-to-table dining, July offers a bustling atmosphere filled with lively events and festivals celebrating the region's rich agricultural heritage. The allure of the sparkling waters and the enchanting landscapes make this time particularly appealing for families and couples alike.

For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, with temperatures dipping to around 0 to 5 degrees Celsius, this off-peak season provides a unique charm. You can experience the tranquillity of the area, enjoy cozy winter activities, and perhaps even find some festive vacation events.
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.
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 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 travellers 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 cosy cabin or a beach house, 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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