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Cutchogue vacation rentals

We found 1,094 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:Jan 16 - Jan 23

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Sit back and relax
9.2 out of 10, Wonderful, (20 reviews)
Wonderful
(20 reviews)

Private Waterfront Home Dock, Kayaks

Southold, NY

7% off
Price is $661
$4,624 for 7 nights
All fees included
Private Waterfront Home Dock, Kayaks

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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.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Sign up today and begin saving right away.

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)
  • Noyac Golf Club (6.5 mi / 10.5 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:

  • Crescent Beach (7.3 mi / 11.7 km)
  • Sunset Beach (7.6 mi / 12.2 km)
  • Meschutt Beach (8.1 mi / 13 km)
  • 67 Steps Beach (9.7 mi / 15.6 km)
  • Cooper's Beach (11 mi / 17.7 km)
  • Ponquogue Beach (12.1 mi / 19.5 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

What is the best area to stay in Cutchogue when booking a vacation rental?
Cutchogue, New York, offers a charming and serene experience, making it an excellent choice for a vacation rental. One of the best areas to consider is near the scenic North Fork vineyards. This region boasts a number of vacation rentals located among picturesque landscapes, with approximately 50 properties available, ensuring a range of options to suit your preferences.

Staying near the vineyards allows easy access to popular attractions, such as the renowned Bedell Cellars and Macari Vineyards, where you can indulge in wine tastings and enjoy the beautiful vineyard views. Additionally, the Cutchogue Village Green is close by, providing a lovely spot for leisurely strolls and picnics.

Another appealing area is closer to the coastline, where you can find charming rentals with views of the Peconic Bay. This location offers proximity to the tranquil beaches, superb for sunbathing and swimming, and is also near the historic Cutchogue Village.
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, New York, travelers should explore the picturesque waterfront areas along the Peconic Bay. The neighborhood near Cutchogue's beaches, such as the serene Cutchogue Harbor, offers vacation rentals that provide stunning bay views and easy access to sandy shores. Many properties in this area come equipped with amenities like outdoor decks, fire pits, and fully stocked kitchens, making them superb for families and groups who want to enjoy the coastal lifestyle.

Additionally, the nearby North Fork area is known for its charming vineyards and farm stands, allowing guests to experience the local flavor. Rentals here often feature spacious yards, barbecue grills, and sometimes even private docks for boating enthusiasts. Visitors can enjoy the tranquility of the region while being close to local attractions such as the picturesque village centers and various outdoor activities, including kayaking and fishing.

For those looking to explore further, the scenic beaches at nearby Mattituck or the family-friendly spots around Southold present additional options. Many beach houses in these neighborhoods come with modern amenities, including air conditioning and Wi-Fi, ensuring a comfortable stay while being just a short drive from local restaurants and shops. Find your rental near the beach in Cutchogue.
What is the most popular type of vacation rental accomodation in Cutchogue?
In Cutchogue, vacation houses are the most popular type of rental, with about 33 available throughout the charming area. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a cozy feel. Many vacation houses also come with outdoor spaces, such as gardens or patios, superb for relaxing after a day of exploring the nearby North Fork wineries and beaches. Additionally, several cozy cottages can be found, providing a quaint and comfortable option for those seeking a more intimate stay.
Are there any family house rentals in Cutchogue?
In Cutchogue, New York, there is a solid selection of family-friendly house rentals—around 33 available throughout the area. This charming town, located on the North Fork of Long Island, offers a picturesque setting for families looking to enjoy a getaway. Many homes come equipped with spacious living areas, full kitchens ideal for preparing meals, and outdoor spaces great for children's play or family gatherings. Visitors can also expect amenities such as Wi-Fi, air conditioning, and often even private pools or backyards for relaxation.

Cutchogue is known for its proximity to beautiful beaches, local vineyards, and scenic parks. Places like the nearby Cutchogue Village Green and the North Fork's renowned wineries provide excellent opportunities for family outings and explorations.
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 14 options to choose from. This charming North Fork community is known for its picturesque vineyards and close proximity to beautiful beaches, making it a great destination for relaxation.

Travelers can expect a variety of amenities in these rentals, including private pools, hot tubs, outdoor entertainment areas, and well-equipped kitchens, great for both unwinding and entertaining. Many properties also offer spacious yards and outdoor dining options, allowing guests to fully enjoy the serene surroundings. Additionally, the area's wineries and local farm stands provide delightful opportunities for exploring the region's culinary offerings.
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, travelers will find a variety of pet-friendly house rentals available, with approximately 13 options to choose from. Many of these vacation homes offer charming amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups traveling with pets.

The Cutchogue area is known for its beautiful vineyards and proximity to picturesque beaches, providing plenty of opportunities for outdoor activities with your furry friends. Nearby, you can explore the scenic Cutchogue Harbor County Park, which features walking trails and waterfront views, superb for leisurely strolls with your pets. Additionally, the local wineries often welcome visitors with pets, allowing for a great experience of wine tasting in a beautiful setting. See all pet-friendly rentals in Cutchogue.
Are there any remote work vacation rentals in Cutchogue?
In Cutchogue, there are numerous options for remote work-friendly vacation rentals, with around 37 available in the area. Travelers can expect properties equipped with essential amenities for a productive stay, including high-speed Wi-Fi, dedicated workspaces with desks and ergonomic chairs, and other conveniences such as safes and computer monitors.

The charming North Fork community offers a peaceful environment, superb for focusing on work while still enjoying the beauty of the surrounding region. Many rentals feature cozy living areas, well-equipped kitchens, and outdoor spaces that provide a pleasant setting to unwind after a day of work. Additionally, Cutchogue is known for its vineyards and scenic views, adding leisure options for when it's time to take a break. 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, vacation rentals commonly feature a variety of amenities that enhance the guest experience. Travelers can expect properties equipped with WiFi, allowing for seamless connectivity during their stay. Kitchens are standard, often including essential appliances such as blenders and coffee makers, which enable guests to prepare their own meals and enjoy home-cooked breakfasts. Many rentals also come with kitchen islands, providing additional space for cooking and dining.
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 vibrant summer months of June through August, with July being particularly popular. This peak season attracts a diverse array of travelers seeking to experience the charming coastal beauty and rich agricultural landscape of Long Island's North Fork. Visitors can enjoy a wide range of outdoor activities, from wine tasting at local vineyards to relaxing on pristine beaches and exploring scenic bike paths.

During July, expect warm temperatures averaging in the mid-80s Fahrenheit, great for enjoying al fresco dining and outdoor festivals. The lively atmosphere is complemented by local events that celebrate the region's bountiful harvests and artistic community, providing ample opportunities for sightseeing and immersion in the local culture.

For those looking to save a bit while still enjoying the area's beauty, consider planning a visit in December. This month offers a unique, quieter charm with festive holiday decorations and cozy spots to unwind after a day of exploring. While the weather is cooler, with temperatures ranging from the low 30s to mid-40s Fahrenheit, the offseason allows for a more intimate experience of Cutchogue's local flavor.

Ultimately, your ideal time to visit Cutchogue will depend on whether you prefer the bustling summer festivities or the peaceful winter atmosphere.
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?
In Cutchogue, visitors can enjoy the charm of the North Fork of Long Island, known for its picturesque vineyards and beautiful beaches. The area is home to several wineries, offering tastings and tours; popular spots include the vineyards along Route 25. Vacation rentals in this region often feature scenic views of grapevines and easy access to tasting rooms.

The nearby Cutchogue Village Historic District provides a glimpse into local history, with quaint shops and eateries. Nature enthusiasts can explore the beautiful beaches at nearby Southold or visit the expansive parks such as the Orient Beach State Park, which offers trails and waterfront access.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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