Country stays in Cutchogue, New York

Welcome to Sweet Dreams Bed & Breakfast Cutchogue, a delightful getaway nestled in the historic hamlet of Cutchogue, New York. Located at 26755 Main Road, our charming 1920's establishment offers a cozy retreat in the heart of the North Fork Wine Country. Our bed and breakfast is perfectly situated within walking distance to local shopping, convenient town transportation, and a variety of attractions including golf courses, vineyards, and farm stands. Whether you're here to explore the peaceful beaches, witness breathtaking sunsets, or enjoy the abundance of hiking and biking trails, Sweet Dreams provides the ideal base for your adventures.

Welcome to Kimberly Krupski, your trusted real estate agent at Daniel Gale Sotheby’s International Realty, located in Cutchogue, New York. Situated at 28080 Main Road, our office is deeply rooted in the heart of the North Fork community. Kim Krupski is not just a real estate agent; she is a 5th generation farmer who grew up on her family's farm in Cutchogue and continues to live there with her husband, Brandon. Her family's land has been a part of the community since 1909, showcasing her deep connections and commitment to the area. Kim is a proud graduate of Mattituck High School and SUNY Geneseo, where she earned a degree in Accounting. Her professional journey took her to the US Department of Agriculture, where she worked for five years, further strengthening her ties to the local community. Currently, she volunteers on the Southold Town Land Preservation Committee, reflecting her passion for preserving the unique character of the North Fork.

Welcome to The Farmhouse Bed and Breakfast, your serene retreat in the heart of Long Island's North Fork. Nestled at 1855 Depot Lane in the charming village of Cutchogue, New York, our delightful B&B offers a perfect blend of rustic charm and modern comfort. Our lovingly restored farmhouse invites you to unwind in one of our cozy, well-appointed rooms, each thoughtfully designed to provide a peaceful haven. Wake up to the aroma of a delicious homemade breakfast, crafted with fresh, locally sourced ingredients to start your day off right.

Welcome to the Railroad Museum of Long Island, a captivating destination for rail enthusiasts and history buffs alike! Located at 440 4th Street, Greenport, New York, our museum is a vibrant hub of railroading heritage, offering a rich tapestry of exhibits and experiences that celebrate the storied past of the Long Island Rail Road (LIRR). This year marks a monumental occasion as we embark on our thirty-fourth season of celebrating railroading on Long Island. Join us for an "Over the Top" season filled with special events and commemorations. We proudly celebrate the 190th Anniversary of the LIRR, which has been operating under the same charter since April 24, 1834. Additionally, we honor the 60th Anniversary of the LIRR Allan Herschel G-16 Park Train, a beloved attraction that began delighting visitors at the 1964 New York World’s Fair.

Welcome to Sannino Vineyard, your idyllic retreat nestled in the heart of Long Island Wine Country at 15975 County Road 48, Cutchogue, New York. As a cherished destination for both food enthusiasts and those seeking a tranquil lodging experience, Sannino Vineyard offers a unique blend of rustic charm and modern comfort. Our vineyard is renowned for producing exquisite wines that reflect the rich terroir of the North Fork. Visitors can indulge in guided tastings and tours, learning about the intricate art of winemaking while savoring our diverse selection of handcrafted wines. Whether you're a wine connoisseur or a casual enthusiast, our friendly and knowledgeable staff are here to enhance your experience.

Welcome to Sunny Side Up Bed and Breakfast, your charming retreat nestled in the heart of Cutchogue, New York. Located at 26350 Main Road, our delightful B&B offers a cozy and inviting atmosphere perfect for a relaxing getaway. Surrounded by the picturesque beauty of the North Fork, Sunny Side Up provides a peaceful escape from the hustle and bustle of everyday life. Our quaint lodging features beautifully appointed rooms, each designed to ensure a comfortable and restful stay. Start your morning with our delicious homemade breakfast, crafted with fresh, local ingredients to give you the perfect start to your day. Whether you're here to explore the stunning vineyards, enjoy the nearby beaches, or simply unwind, Sunny Side Up Bed and Breakfast is your ideal home away from home.