Southold vacation rentals

Why visit Southold

1. Beautiful Beaches: Enjoy the stunning coastal scenery and relax on Southold's pristine beaches, perfect for sunbathing and swimming.
2. Outdoor Adventures: Explore various outdoor activities, from hiking to biking, in the picturesque surroundings of Southold.
3. Charming Parks: Visit urban parks that offer a serene atmosphere for picnics, leisurely strolls, and family-friendly excursions.
4. Art Galleries: Discover local art galleries showcasing unique works and supporting the vibrant artistic community.
5. Cozy Accommodations: Choose from a variety of charming rentals, including private homes and cottages, for a perfect getaway.

Popular types of accommodation in Southold

Planning a getaway to Southold? You've made a fantastic choice! Now, let's find you the perfect place to stay. From charming houses and cozy cottages to stylish apartments, Southold offers a variety of vacation rental options. Whether you're looking for summer rentals or spacious homes for rent, you're sure to find the ideal townhouse rentals that meet your needs. Explore your options and get ready for an unforgettable stay!

• Houses: The top choice for visitors to Southold, ideal for families or groups seeking a comfortable and spacious stay.
• Cottages: A charming option that offers a quaint and cozy atmosphere, perfect for a peaceful getaway.
• Apartments: Convenient and often centrally located, these rentals provide a home-like experience for solo travelers or couples.
• Condos: A great choice for those looking for modern amenities and shared facilities in a community setting.
• Villas: Luxurious and spacious, these properties offer an upscale experience with beautiful surroundings.**

Top attractions near Southold

Southold, New York, offers a delightful vacation experience for outdoor enthusiasts and couples alike. With its beautiful beaches, charming urban parks, and fascinating history museums, visitors can enjoy a blend of culture and relaxation. Explore the scenic town of Southold and indulge in various activities that cater to both adventure seekers and those looking for a romantic getaway. Don't miss the chance to create lasting memories in this picturesque destination.

1. 67 Steps Beach: A charming beach located 5 miles from Southold, offering a relaxed atmosphere and stunning ocean views. The unique staircase leading down to the beach adds character, making it a perfect spot for sunbathing and beachcombing.
2. Sag Harbor Marine Park: Situated 8 miles away, this marina features beautiful waterfront views and outdoor activities. Enjoy boating, fishing, and picnicking in a scenic setting, ideal for adventure seekers and families alike.
3. Railroad Museum of Long Island: Just 4 miles from Southold, this museum showcases the rich history of railroads in the region. Explore fascinating exhibits and vintage trains, immersing yourself in the cultural heritage of Long Island.

Things to do recommended for couples

For a romantic getaway in Southold, visit Pindar Vineyards for a delightful wine tasting experience. Enjoy a fun round of mini-golf at Shelter Island Whale's Tail, then savor a cozy dinner at Indian Wells Beach, where you can relish great food in a charming atmosphere.

Things to do recommended for families

Your family will love the Greenport Carousel, just 4 miles from Southold, offering delightful rides in a charming outdoor setting. For relaxation, head to Goldsmith's Inlet Park, 3 miles away, or enjoy a day of adventure at Splish Splash Water Park, located 19 miles from Southold.

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

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences with the right filters. 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 full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
• Traveling to Southold with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with having suitable amenities like a private 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 vacation just isn’t the same without their furry companion by their side. If that resonates with you, take a look at Vrbo listings 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 vacation rentals with special offers for month-long stays, you've come to the right spot. By using the appropriate filters, you can easily 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 as well.

Where to stay near Southold

Southold, New York, offers a perfect blend of outdoor adventures and romantic getaways. Enjoy sunny weather while exploring nearby neighborhoods that boast stunning scenery and family-friendly excursions. From luxurious local art galleries to charming coastal spots, Southold is an ideal destination for your next vacation. Experience the vibrant atmosphere of summer in Southold, where every moment promises delightful memories and unforgettable experiences.

• Greenport: Nestled just 4 miles from Southold, Greenport is a charming waterfront village that beckons travelers with its outdoor allure and romantic coastal vibes. This picturesque locale is perfect for those looking to unwind by the beach or enjoy a leisurely stroll along its historic streets. Greenport offers a variety of attractions, including casinos and golf courses, making it ideal for both relaxation and entertainment. Don't miss the opportunity to visit local beaches and event venues, where you can soak up the sun or participate in community activities.
• Southampton: Located 13 miles from Southold, Southampton is renowned for its stunning beaches and vibrant outdoor experiences. This upscale community is a favorite among those seeking romance and adventure alike. Enjoy a day of sunbathing on family-friendly beaches, or engage in various outdoor activities like golf and skiing nearby. With serene lakes and scenic landscapes, Southampton is a perfect escape for nature lovers and beach enthusiasts. Experience the charm of this coastal gem as you indulge in leisurely walks and local dining options.
• Sag Harbor: Situated 8 miles from Southold, Sag Harbor is a quaint town rich in maritime history and natural beauty. Visitors are drawn to its outdoor recreational opportunities and beautiful beaches, perfect for a day of sun and sand. The town features inviting parks and family-friendly beaches, making it an excellent destination for travelers of all ages. Sag Harbor also boasts a variety of attractions, including golf courses and skiing options, ensuring that there's something for everyone. Embrace the relaxed atmosphere of this charming town as you explore its stunning waterfront and vibrant community.

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

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner certainly has its perks! By becoming a part of our travel rewards program, One Key, you can immediately access member discounts and accumulate OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to create new travel plans, manage your existing arrangements, and organize your bookings more effectively. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.