Southold holiday lettings

Why visit Southold

• Picturesque Beaches: Southold boasts stunning coastal views and serene sandy shores, perfect for relaxation and sunbathing.
• Historic Lighthouses: Explore charming lighthouses that offer a glimpse into the town's maritime heritage.
• Vineyards and Wineries: Discover local vineyards where you can enjoy tastings of exquisite wines amidst beautiful landscapes.
• Outdoor Activities: Engage in cycling, hiking, and fishing along scenic routes and tranquil waters.
• Cultural Experiences: Visit local museums and galleries that showcase Southold's rich history and artistic flair.

Popular types of accommodation in Southold

Your adventure in Southold, New York, awaits. Nestled on the picturesque North Fork, Southold boasts charming private homes, delightful cottages, and comfortable apartments for your stay. Explore local attractions such as the scenic beaches, historic lighthouses, and tranquil vineyards. Enjoy outdoor activities like cycling along the coastline or tasting fresh seafood at local eateries. Discover the perfect Southold rental that suits your needs and immerse yourself in this idyllic coastal town.

• Houses: The top choice for visitors in Southold, offering spacious and comfortable living spaces for families or groups.
• Cottages: Charming and quaint, these lovely retreats provide a cosy atmosphere, perfect for a romantic getaway.
• Apartments: Convenient and stylish, ideal for solo travellers or couples seeking a home away from home.
• Condos: Modern and well-equipped, perfect for those who enjoy amenities and community facilities.
• Villas: Luxurious and spacious, offering upscale living with stunning views for a lavish holiday experience.**

Top attractions in and around Southold

Southold, New York, offers a delightful blend of outdoor activities and cultural experiences perfect for a romantic getaway or an entertaining trip. Visitors can enjoy the picturesque beaches, explore lush urban parks, and delve into local history at its museums. This charming town caters to those seeking relaxation by the shore, immersive cultural encounters, and memorable outdoor adventures, making it an ideal destination for travellers looking to unwind and explore.

• Horton Lane Beach: A serene stretch of sand perfect for relaxation, offering stunning views and a tranquil atmosphere, ideal for sunbathing and swimming.
• Orient Point County Park: A family-friendly park featuring lush landscapes, picnic areas, and walking trails, perfect for outdoor activities and enjoying nature.
• Sag Harbor Marine Park: An adventurous marina where you can engage in various water sports, explore the beach, and soak in the vibrant marina atmosphere.

Things to do recommended for couples

Southold offers a charming escape for couples. Explore the serene vineyards with a wine tasting, stroll along the pristine beaches, or enjoy a scenic bike ride through the picturesque countryside. Don’t miss a sunset picnic by the water for a truly romantic evening.

Things to do recommended for families

Families will delight in the sandy shores of Southold's beautiful beaches, explore the interactive exhibits at the Southold Historical Society, or enjoy a fun day picking fresh fruit at local farms. Don't miss the charming shops and eateries that offer a taste of the area's unique culture.

Things to do recommended for groups

Experience the thrill of motor racing at Riverhead Raceway, located 29km from Southold. Gather your group for an adrenaline-fuelled day filled with sports and adventure vibes, perfect for creating unforgettable memories together.

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

When travelling with a group, family, pets, or seeking longer stays, it's important to use filters that align with your specific needs. Here are some helpful booking tips for Vrbo.

• Traveling to Southold with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
• Traveling to Southold with young kids: Travelling with young children can indeed be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities, such as a private swimming pool. Additionally, it would be wise to think about your closeness to family-friendly attractions.
• Taking your pets with you to Southold: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many 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 in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to consider adding features such as a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay near Southold

Southold, New York, offers a delightful blend of outdoor adventures and romantic experiences, perfect for a memorable vacation. Visitors can explore the charming landscapes, indulge in family-friendly activities, and soak up the sunny weather. The town is rich in history and scenic beauty, making it an ideal destination for excursions. Whether you’re enjoying a leisurely stroll along Soundview Avenue or discovering the local wineries, Southold promises a captivating getaway for all travellers.

• Hamptons: Situated approximately 16km from Southold, the Hamptons are renowned for their stunning beaches and outdoor activities, making it a prime destination for those seeking a romantic escape. Visitors can indulge in golfing at exquisite courses or enjoy the snowy slopes during winter. Highlights include charming local beaches, family-friendly shores, and picturesque lakes that offer a serene backdrop for relaxation and recreation. Whether you're lounging on the beach or exploring quaint local shops, the Hamptons promise a delightful getaway.
• Greenport: Just 6km away from Southold, Greenport is a charming coastal town that captivates visitors with its outdoor allure and romantic ambiance. This delightful city offers a variety of activities, including access to golf courses and vibrant recreational areas, as well as an array of music concerts throughout the year. The local attractions, such as its beautiful beaches, family-friendly shores, and lush parks, provide ample opportunities for adventure and relaxation. Greenport's inviting waterfront and friendly atmosphere make it a must-visit destination.
• Sag Harbor: Located about 13km from Southold, Sag Harbor is an enchanting city with a rich maritime history that attracts outdoor enthusiasts and romantics alike. The area boasts excellent golf courses, scenic beaches, and tranquil lakes, perfect for a leisurely day out. Visitors can enjoy a variety of activities, from sunbathing on family beaches to exploring the surrounding natural beauty. With its quaint streets and vibrant arts scene, Sag Harbor offers a unique blend of relaxation and culture, making it an ideal spot for a memorable vacation.

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

Booking with Vrbo is a breeze

Looking to enjoy savings on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant discounts. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your journeys, allowing you to easily create new trips, resume where you left off, and organise your existing plans. You can view your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Southold

The area's wineries and monuments are just some of the reasons to come on holiday to Southold. Renowned for its island views, beaches and gardens, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Southold

Are you looking for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southold a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

• Croteaux Vineyards (1.5 mi / 2.4 km)
• Raphael Winery (2.7 mi / 4.4 km)
• Pindar Vineyards (3 mi / 4.9 km)
• Bedell Cellars (3.3 mi / 5.3 km)
• Peconic Bay Winery (4.2 mi / 6.8 km)
• Kontokosta Winery (4.7 mi / 7.6 km)

Exploring the natural landscape of Southold

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Southold is a great spot to appreciate mother nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

• Crescent Beach (2.9 mi / 4.7 km)
• Sunset Beach (3.2 mi / 5.2 km)
• 67 Steps Beach (4.8 mi / 7.8 km)
• Elizabeth A. Morton National Wildlife Refuge (6.1 mi / 9.8 km)
• The Hamptons Beaches (11.6 mi / 18.6 km)
• Orient Point County Park (11.7 mi / 18.8 km)

Transport to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you prefer train travel, the main station is Southold Station.