The Southold Escape

Tucked away in the heart of Southold’s wine country, this chic, modern retreat offers a resort-style escape that feels worlds away from the everyday. Thoughtfully designed for the discerning traveler, this property is more than just a vacation rental — it’s an experience. From the moment guests arrive, they’re greeted with the refined sophistication of a designer home paired with the relaxed charm of the North Fork. With 4 bedrooms, 2.5 bathrooms, and a stand-alone guest house, this home comfortably accommodates up to seven guests, offering luxurious comfort and privacy for families, friends, or couples traveling together. Sun-drenched interiors, curated art, and open-concept indoor-outdoor living make this destination truly unforgettable.

Step into the expansive, fully fenced backyard and discover a personal paradise where every detail invites relaxation and connection. Lush landscaping creates a private oasis that wraps around the heated pool and built-in pool house, providing total seclusion. Guests can bask in the sun on chaise loungers atop the spacious sundeck or gather around the outdoor dining table for al fresco meals beneath the stars. The outdoor gas grill sets the stage for summer barbecues, while the paved firepit area promises cozy evenings with cocktails and conversation. Multiple seating areas, both covered and open-air, make it easy to entertain or retreat into solitude. It’s a setting that evokes the atmosphere of a private resort, with all the comforts of home — and plenty of free parking makes arriving and departing effortless.

Inside, the home welcomes guests with a warm, earthy elegance that combines modern lines with rustic, elevated touches. Natural light pours in through large windows, highlighting the home’s stylish décor and thoughtfully curated art. The main level flows seamlessly between the formal living room, dining room, and chef’s kitchen — a perfect layout for entertaining or relaxing. The living room is anchored by plush sofas and sweeping views of the pool and backyard, while the adjoining dining room features a striking table that seats eight comfortably. The kitchen is a dream for anyone who loves to cook or host, outfitted with top-of-the-line appliances, a spacious island, and all the tools and tableware needed for memorable meals. A wet bar on the main level adds to the home’s social appeal, while a private office with a desk and sofa provides a quiet place to work or read. Additional amenities include central AC, high-speed WiFi, and a washer/dryer, making longer stays comfortable and convenient.

Each of the four bedrooms has been designed with serenity in mind, offering stylish, restful retreats outfitted with fresh linens and high-quality finishes. The primary suite, located on the second level, is a showstopper — a vaulted ceiling and rustic wood paneling create an elevated yet cozy vibe. The adjacent spa-like bathroom features a luxurious walk-in shower and a freestanding soaking tub for the ultimate indulgence. Also on the second level is a guest room with a full bed, perfect for couples or solo travelers. A third bedroom, located on the main floor, offers a charming bunk bed setup ideal for children or close friends, with a stylish full bathroom just steps away. The fourth bedroom is housed in a beautifully designed guest cottage with wood-paneled walls and ceilings, a king-sized bed, a half bath, and its own kitchenette — perfect for added privacy or a quiet escape.

Just minutes from the home, guests can explore the best of the North Fork. Southold’s charming downtown is close by, where boutique shops, locally-owned restaurants, and art galleries provide plenty to see and do. Spend the day browsing unique antiques or sampling gourmet fare at one of the area’s celebrated eateries. For wine lovers, the region’s famed vineyards are just a short drive away, offering tastings, tours, and unforgettable views. Beaches dot the coastline within a few minutes’ reach, perfect for a morning walk, an afternoon swim, or a sunset picnic. Whether strolling through local farmers’ markets or enjoying fresh oysters by the water, guests will find that everything they need is nearby — yet the peace and privacy of the home always feel a world apart.

Designed for travelers who appreciate style, space, and serenity, this Southold gem offers more than just a place to stay. It’s a destination in its own right — a refined, welcoming home where every detail is curated for connection, celebration, and escape.