Southold vacation rentals

Why visit Southold

• Beautiful Beaches: Southold boasts stunning beaches perfect for relaxation and water activities.
• Outdoor Adventures: Ideal for nature lovers, Southold offers various outdoor activities, from hiking to biking.
• Rich History: Explore fascinating history museums and learn about the area's cultural heritage.
• Charming Neighborhoods: Discover picturesque neighborhoods featuring luxury homes and scenic views.
• Cozy Accommodations: Choose from a variety of vacation rentals, including charming cottages and stylish apartments.

Popular types of accommodation in Southold

Planning a getaway to Southold? You're in for a treat. This charming destination offers a variety of vacation rentals, including private homes, cozy cottages, and stylish apartments. Whether you're searching for spacious townhouse rentals or inviting houses, Southold has something for everyone. Explore the options and find the perfect Southampton home for rent to make your stay memorable.

• Houses: The top choice for travelers in Southold, offering spacious and comfortable accommodations for families or groups seeking a home-like experience.
• Cottages: A charming option, perfect for those wanting a cozy retreat surrounded by nature and local character.
• Apartments: Ideal for solo travelers or couples, these rentals provide convenience and a taste of local living.
• Condos: A popular choice for those looking for modern amenities and access to community features.
• Villas: Luxurious spaces that offer a more upscale experience for those seeking relaxation and privacy.**

Top attractions near Southold

Southold, New York, is a fantastic destination for outdoor enthusiasts, couples, and those seeking entertainment. With a variety of attractions, including beautiful beaches, urban parks, and fascinating history museums, visitors can immerse themselves in the area's culture and natural beauty. Whether you're looking for a romantic getaway or an outdoor adventure, Southold offers something for everyone to enjoy during their vacation.

• 67 Steps Beach: Located 5 miles from Southold, this beach offers a serene escape with its picturesque views and tranquil atmosphere. The unique 67 steps leading to the sandy shore enhance its charm, making it perfect for relaxation and sunbathing.
• Railroad Museum of Long Island: Just 4 miles away, this museum showcases the rich history of railroads in the region. With engaging exhibits and historic trains, it offers a cultural experience for enthusiasts and families alike.
• Sag Harbor Marine Park: Situated 8 miles from Southold, this marina provides an outdoor adventure with opportunities for kayaking, fishing, and picnicking. Its scenic waterfront and beach vibes make it a perfect spot for exploration.

Things to do recommended for couples

Experience romance in Southold with a visit to Pindar or Raphael Vineyards, both offering delightful wine tastings just 3 miles away. For a fun twist, head to Shelter Island Whale's Tail mini golf, only 5 miles away, perfect for a playful couple's outing.

Things to do recommended for families

Families can experience the charming Greenport Carousel just 4 miles away, unwind at Goldsmith's Inlet Park 3 miles away, or enjoy the thrilling rides at Splish Splash Water Park located 19 miles from Southold. Each spot offers unique fun and relaxation for all ages.

Things to do recommended for groups

Explore the Greenport Farmers' Market for local produce, tee off at Noyac Golf Club for a fun day outdoors, and catch a show at Bay Street Theatre for a memorable evening filled with culture and entertainment. These experiences promise a fantastic group getaway in Southold.

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

If you're planning a trip with a group, traveling with family, bringing your pets along, or seeking extended stays, be sure to filter your options according to your key priorities. Here are some helpful tips for booking on 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 areas for group gatherings. Luckily, you can easily filter for these options and many 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 suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
• Taking your pets with you to Southold: For many families, a vacation wouldn’t feel complete without their furry companion. If you can relate, explore 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 offering discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Southold

Southold offers a charming escape with its serene surroundings and outdoor activities perfect for romantic getaways or family adventures. Explore the nearby neighborhoods, where luxury homes and picturesque scenery await. Experience the rich history and vibrant atmosphere of New York’s North Fork, with its family-friendly attractions and exquisite excursions. Whether you're looking for a vacation home or just a peaceful retreat, Southold promises an unforgettable experience.

• Hamptons: Located approximately 10 miles from Southold, the Hamptons are renowned for their stunning beaches and outdoor activities, making it a prime destination for romantic getaways. Visitors can indulge in a round of golf, attend music concerts, or relax at luxurious resorts. The beautiful beaches, including family-friendly spots and serene lakes, offer ideal settings for sunbathing, swimming, and picnicking, ensuring a memorable coastal experience.
• Greenport: Just 4 miles from Southold, Greenport is a charming city known for its outdoor adventures and romantic atmosphere. The waterfront town features a variety of activities, from golfing to live music events. Visitors can explore picturesque beaches, family-friendly shores, and event venues that host conferences and gatherings. Greenport's vibrant maritime history and local eateries provide a delightful experience for tourists seeking a blend of relaxation and entertainment.
• Sag Harbor: Situated about 8 miles from Southold, Sag Harbor captures the essence of seaside charm with its outdoor activities and beautiful beaches. This historic city is perfect for romantic excursions, featuring golf courses and nearby ski fields for winter enthusiasts. Local attractions include serene beaches, family-friendly areas, and lovely parks, making Sag Harbor a fantastic spot for both relaxation and recreation. Enjoy the picturesque views and warm community vibe as you explore this delightful destination.

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 simple

Are you hoping to save money on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of even greater savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your trip.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly area to plan new trips, continue your previous arrangements, or manage your travel itinerary. You'll easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Southold

The area's wineries and monuments are just a few of the reasons to vacation in 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 hoping to discover things to do in the city? Venture out of your vacation home and experience everything that makes Southold a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

• 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 spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Southold. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

• 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)

Transportation to and around Southold

The nearest airport is in East Hampton, NY (HTO), located 11.8 mi (18.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away.

If you'd prefer to travel by train, you can make your way to Southold Station.