Southold holiday homes

Why visit Southold

• Sunny Beaches: Enjoy Southold’s beautiful, family-friendly beaches perfect for soaking up the sun and relaxing.
• Urban Parks: Explore the town's serene parks, ideal for picnics and leisurely strolls amidst nature.
• Rich Local History: Delve into Southold’s museums that showcase its fascinating cultural and historical heritage.
• Scenic Landscapes: Discover picturesque views along Soundview Ave, offering a blend of natural beauty and local charm.
• Outdoor Adventures: Engage in a variety of activities that celebrate Southold’s inviting outdoor allure.

Top attractions near Southold

Southold, New York, offers a charming blend of outdoor adventures and romantic escapes. Visitors can relish the sun at its beautiful beaches, explore urban parks, and delve into local history at its museums. With a focus on culture and nature, Southold caters to those seeking a laid-back yet enriching experience, making it perfect for families, couples, and solo travellers alike.

• The Hamptons Beaches: Enjoy the relaxed beach vibes with sun-soaked sands and refreshing ocean breezes, ideal for unwinding near Southold, 19km away.
• Sag Harbor Marine Park: Experience adventure and outdoor excitement at this marina, perfect for water activities and seaside explorations, located 13km from Southold.
• Foster Memorial Town Beach: Engage with city and family-friendly outdoor fun at this urban park, offering a dynamic blend of coastal and urban experiences, situated 11km from Southold.

Things to do recommended for couples

Southold offers a delightful escape for couples. Explore the scenic vineyards, indulge in local wine tastings, or take a romantic stroll along the picturesque beaches. Don’t miss a sunset picnic at the park, where you can savour the serene beauty together.

Things to do recommended for families

Families visiting Southold can enjoy a fun-filled day exploring local coastal parks and interactive museums, perfect for sparking young imaginations and creating lasting memories.

Things to do recommended for groups

Groups visiting Southold can experience the thrill of motor racing at Riverhead Raceway, located 29km away. Enjoy the adrenaline-fueled atmosphere, perfect for adventure seekers and sports enthusiasts alike.

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

When travelling with a group, family, pets, or planning for extended stays, it’s important to prioritise your preferences when filtering your options. Here are some helpful Vrbo booking tips to guide you.

• Traveling to Southold with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas 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 be quite demanding. It’s important to prioritise their comfort and safety, along with suitable amenities 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, a family holiday wouldn’t be the same without their furry companion. If that resonates with you, take a look at 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 searching for holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Southold

Discover the charm of Southold, where sunny weather and a family-friendly vibe set the scene for a memorable getaway. Embrace the outdoor allure and romantic ambience of the town, explore Soundview Ave, and experience the historical and luxury touches of summer in Southold. Enjoy excursions that celebrate the scenic landscapes and rich history inherent in this unique destination.

• Hamptons: A short 16km trip from Southold, the Hamptons beckon with a blend of outdoor charm and romantic allure. Visitors are drawn to its pristine beach settings, ideal for a leisurely day by the sea or a family visit. The area offers diverse recreational activities, including a well-maintained golf course and even a ski field for the winter months. With a local lake and family beach within easy reach, the Hamptons provide a well-rounded experience for those seeking both relaxation and a touch of adventure.
• Greenport: Just 6km from Southold, the city of Greenport is a gem for travellers eager to embrace the outdoors. Its scenic beaches and inviting parks set the stage for a romantic and active getaway. Alongside exploring the coastline and family-friendly beach areas, visitors can enjoy the golf course and recreational areas, as well as catch a music concert that highlights the local vibrant music scene. Greenport presents a balanced mix of natural beauty and cultural attractions, perfect for a memorable holiday experience.
• Sag Harbor: Located 13km from Southold, Sag Harbor offers a picturesque retreat with a focus on outdoor and beach experiences. The area is celebrated for its tranquil family beach and nearby lake, providing an idyllic backdrop for a romantic outing or a leisurely day in nature. With opportunities to partake in golf and even try skiing, Sag Harbor is well suited for those who appreciate a diverse range of activities, from active pursuits to simply soaking in the coastal charm.

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.

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

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's innovative Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or review and organise your travel plans. You can easily access the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.bookabach.co.nz/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:

• 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)
• Noyac Golf Club (6.5 mi / 10.4 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:

• Sunset Beach (3.2 mi / 5.2 km)
• 67 Steps Beach (4.8 mi / 7.8 km)
• The Hamptons Beaches (11.6 mi / 18.6 km)
• Orient Point County Park (11.7 mi / 18.8 km)
• Meschutt Beach (12.4 mi / 19.9 km)
• LongHouse Reserve (13.1 mi / 21.1 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.