Southold holiday lettings

Why visit Southold

• Beautiful beaches: Southold boasts stunning sandy shores, perfect for sunbathing and relaxation.
• Historic charm: Wander through quaint streets lined with historic houses, immersing yourself in local heritage.
• Outdoor activities: Enjoy a range of outdoor pursuits, from hiking in tranquil parks to family-friendly excursions.
• Scenic neighbourhoods: Explore picturesque areas offering scenic views and luxury experiences.
• Comfortable accommodations: Choose from charming cottages to modern apartments, catering to every traveller's needs.

Popular types of accommodation in Southold

Discover a variety of vacation rentals in Southold, perfect for your getaway. Whether you’re seeking a charming cottage, a spacious private home, or a modern apartment, we have something to suit every traveller. Popular options include holiday homes, condos, and townhouse rentals, ensuring a comfortable stay tailored to your needs. Explore Southold and create lasting memories with the ideal accommodation choice for your trip.

• Houses: The top choice for visitors in Southold, these homes offer spacious and comfortable accommodations perfect for families or groups.
• Cottages: A charming option, cottages provide a quaint and cosy atmosphere, ideal for a peaceful getaway.
• Apartments: Popular among solo travellers and couples, apartments offer convenience and flexibility during your stay.
• Condos: These modern dwellings combine luxury with practicality, making them a sought-after option for vacationers.
• Villas: For those seeking elegance, villas offer upscale living with ample space and amenities.**

Top attractions near Southold

Southold offers a delightful blend of outdoor activities, romantic spots, and vibrant entertainment options, making it an ideal vacation destination. Visitors can explore beautiful beaches, tranquil urban parks, and fascinating museums that reflect the area's rich history. Whether you're seeking a cultural experience or simply wish to enjoy the great outdoors, Southold has something to cater to every traveller's preference.

• 67 Steps Beach: A beautiful sandy beach offering a relaxing atmosphere, 67 Steps Beach is perfect for sunbathing and swimming. Enjoy the soothing sounds of the waves as you unwind in this picturesque coastal setting, located 3.1km from Southold.
• Railroad Museum of Long Island: Immerse yourself in local culture at this fascinating railway museum, showcasing historical trains and exhibits. Just 2.5km from Southold, it's a delightful trip for history buffs and families alike.
• Sag Harbor Marine Park: Experience adventure at this vibrant marina, 5.0km from Southold, where you can partake in water sports, fishing, and outdoor activities while enjoying stunning views of the waterfront.

Things to do recommended for couples

Planning a romantic getaway in Southold? Delight in wine tasting at Pindar Vineyards or Raphael Winery, both offering enchanting atmospheres. For a touch of adventure, enjoy a round of mini golf at Shelter Island Whale's Tail, perfect for creating cherished memories together.

Things to do recommended for families

Families will love the charming Greenport Carousel, a delightful outdoor attraction just 2.5km from Southold. For relaxation, visit Goldsmith's Inlet Park, 1.9km away. For adventure, the Splish Splash Water Park, located 11.8km from Southold, offers fantastic entertainment for all ages.

Things to do recommended for groups

Explore the Greenport Farmers' Market for a taste of local produce and vibrant community spirit, enjoy a round of golf at Noyac Golf Club amidst beautiful surroundings, and catch a performance at the Bay Street Theatre for a delightful evening of culture and entertainment.

Booking with Vrbo is simple

Are you hoping to save on your next getaway? It’s worth being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, make use of our filters to refine your search by price, location, and type of holiday rental.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic escapades, perfect for a memorable getaway. Explore the charming streets lined with historic houses, enjoy family-friendly excursions, and soak up the sunny weather. Nearby, discover picturesque neighbourhoods boasting scenic views and luxury experiences. Whether you're wandering through Southold Town or seeking the best spots for relaxation, this region is sure to captivate every traveller.

• Hamptons: Situated approximately 6.2km from Southold, the Hamptons are renowned for their picturesque beaches and upscale atmosphere. This idyllic retreat is a favourite for couples seeking a romantic getaway, as well as families eager to enjoy outdoor activities. Visitors can indulge in a round of golf, attend a lively music concert, or relax at luxurious resorts. Notable nearby attractions include pristine beaches, family-friendly shorelines, and serene lakes, making it a perfect destination for sun-seekers and nature lovers alike.
• Greenport: Located a mere 2.5km away from Southold, Greenport is a charming town that offers a delightful mix of outdoor experiences and romantic settings. Its scenic waterfront and quaint streets invite exploration, whether you're enjoying a day at the beach or attending a local event at a conference venue. The area is also home to various golf courses and music venues. Greenport’s local landmarks, including family beaches, make it a welcoming spot for visitors looking to unwind and embrace the beauty of coastal living.
• Sag Harbor: Nestled 5.0km from Southold, Sag Harbor boasts a rich maritime history and a vibrant community atmosphere. This coastal town is celebrated for its outdoor spaces and beautiful beaches, making it an ideal location for romantic strolls or family outings. Visitors can partake in activities such as golfing or skiing, adding an adventurous twist to their stay. Local highlights include family beaches and picturesque parks, offering ample opportunities for relaxation and recreation amidst Sag Harbor's stunning natural surroundings.

Best time to go to Southold

If you're planning a trip to Southold, 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 November to January tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Moderately Low	Moderately Low
February	35.8°F (2.1°C)	Light Rain	Mostly Cloudy	Average	Moderately Low
March	39.7°F (4.3°C)	Light Rain	Mostly Sunny	Average	Moderately Low
April	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Average
May	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Average	Average
June	64.9°F (18.3°C)	Light Rain	Mostly Sunny	Moderately High	Moderately High
July	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Moderately High	Moderately High
August	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Moderately High
September	68.2°F (20.1°C)	Light Rain	Mostly Sunny	Average	Average
October	59.7°F (15.4°C)	Light Rain	Mostly Sunny	Average	Average
November	49.6°F (9.8°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	42.1°F (5.6°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

What do I need to keep in mind when booking a vacation in 'Southold

When planning your journey, whether it’s with a group, family, or pets, or if you’re seeking a longer stay, be sure to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

• Traveling to Southold with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
• Traveling to Southold with young kids: Travelling with young children can present its difficulties. It's essential to prioritise their comfort and safety, along with suitable facilities 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 Southold: For many families, a holiday isn’t truly enjoyable without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Southold: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated space to plan new trips, pick up from where you last stopped, or view and arrange your travel plans. You can conveniently find properties you've previously saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.