Hotels in Southold

Southold, located in the picturesque North Fork region of Long Island, offers a plethora of exciting activities for travelers of all ages. With its abundance of wineries, visitors can indulge in tastings and tours, or even plan a romantic winery wedding. For those who enjoy the outdoors, Southold boasts beautiful beaches and gardens, perfect for leisurely strolls or picnics. Boat enthusiasts can take advantage of the area's marinas and explore the surrounding islands. Families will find plenty of children-friendly activities, including interactive museums and farm visits. And don't miss the chance to visit the renowned North Fork vineyards for a taste of the region's finest wines.

1. Croteaux Vineyards: Experience the enchanting charm of Croteaux Vineyards. Nestled amidst picturesque winery, beach, and biking trails, this destination is a haven for wine lovers. With its close proximity to islands and a bustling port, you can indulge in a romantic getaway or enjoy a family-friendly outing. The breathtaking sunsets over the sea add a touch of magic to the ambiance. Don't miss out on the opportunity to savor their delightful wines while soaking in the serene opera-inspired atmosphere.
2. Horton Point Park: Immerse yourself in the rich cultural heritage of Horton Point Park. This historic lighthouse point of interest is surrounded by stunning islands, vineyards, and scenic biking trails. With its beautiful beach, family-friendly atmosphere, and captivating sunsets, this destination offers a unique blend of natural beauty and cultural experiences. Explore the port, go boating or sailing, and embrace the tranquility of nature as you discover the stories and history that this park has to offer.
3. Sparkling Pointe: Embark on a sparkling adventure at Sparkling Pointe. This alcohol winery point of interest is a true gem, with its proximity to a winery, islands, and breathtaking biking trails and beach. Whether you're seeking entertainment or a romantic experience, this destination has it all. Enjoy the family-friendly atmosphere, explore the vibrant port, and indulge in boating or sailing. As the sun sets over the sea, immerse yourself in the serene ambiance and savor the exquisite flavors of their sparkling wines.

Experience the best of Southold's outdoor vacation with its stunning wineries, family-friendly activities, and beautiful beaches. Explore the charming islands, dance the night away, and bask in the sunny weather. Southold, located on Long Island's North Fork, offers a vibrant downtown with plenty of monuments and breathtaking sunsets.

1. East Hampton: East Hampton, located just 14.4 miles away from Southold, is a must-visit destination for outdoor enthusiasts. This popular city offers a unique experience with its charming port, thrilling shark sightings, and beautiful islands. Dive into the depths of the sea for a memorable diving adventure or try your hand at hunting in the surrounding wilderness. East Hampton is also known for its delectable seafood and stunning sea views. And if you're looking for some excitement, catch the perfect wave while surfing along the coast. With its diverse range of activities, East Hampton is the ideal destination for an outdoor holiday.
2. Southampton: Just 12.6 miles away from Southold, Southampton is a city that should not be missed by outdoor enthusiasts. This vibrant city offers a unique experience with its picturesque biking trails, fascinating museums, and lively festivals. Immerse yourself in the world of arts and culture by catching an opera performance or admiring the vibrant flowers in the local gardens. Explore the beautiful churches and cathedrals, or marvel at the historical monuments scattered throughout the city. And of course, don't forget to relax on the pristine beaches or catch a show at the theater. Southampton has it all for an unforgettable outdoor holiday.
3. Greenport: Just 4.4 miles away from Southold, Greenport is a hidden gem for outdoor enthusiasts. This charming city offers a unique experience with its stunning natural beauty, family-friendly atmosphere, and bustling port. Spend your days exploring the beautiful beaches or embark on a boating adventure to discover the nearby islands. Immerse yourself in the lively festivals and enjoy exciting ferry excursions. And as the sun sets, witness the breathtaking colors painting the sky. Greenport is the perfect destination for those seeking an outdoor holiday filled with relaxation, adventure, and unforgettable moments.

Southold, located in the picturesque hamlet of Southold on Long Island's North Fork, offers a diverse and vibrant dining scene. For seafood lovers, Southold Fish Market is a highly rated and popular choice, serving up fresh and succulent seafood dishes. If you're in the mood for Mediterranean and Italian cuisine, Waypoint Restaurant is a must-visit. Their menu features a delightful blend of flavors and tastes. For a taste of North American and New American cuisine, head to the renowned North Fork Table & Inn. With its exceptional dishes and cozy ambiance, it's a favorite among locals and visitors alike.