Town of Southold Town vacation rentals

We found 4,445 vacation rentals — enter your dates for availability

Select from 437 homes, 52 cottages, and other vacation rentals in Town of Southold Town to find one that's perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, such as WiFi and a fireplace. At the end of the day, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Town of Southold Town

Find out more about Town of Southold Town

Why visit Town of Southold Town

  1. Beautiful Beaches: Relax at charming beaches, perfect for unwinding and enjoying sunny weather.
  2. Outdoor Activities: Engage in paddleboarding and explore scenic parks, ideal for adventure seekers.
  3. Charming Farms: Visit local farms to experience the area's agricultural heritage and fresh produce.
  4. Picturesque Getaway: Enjoy a romantic atmosphere with stunning coastal views and memorable photo opportunities.
  5. Diverse Accommodations: Choose from cozy cottages, private homes, or comfortable apartments for a homey stay.

Popular types of accommodation in Town of Southold Town

Planning a getaway to the Town of Southold Town? You're in for a treat! This beach paradise offers a variety of accommodations, including houses, apartments, and charming cottages. Enjoy the sun at dog-friendly beaches, and don’t worry about parking—Southold Town permits make it easy. Plus, you can stay active at local health clubs. Explore your options and find the perfect rental for an unforgettable stay!

  • Houses: The top choice for visitors, offering spacious and comfortable living for families or groups in Southold Town.
  • Apartments: A favored option for those seeking a cozy, self-contained space with essential amenities during their stay.
  • Cottages: Charming and quaint, these rentals provide a picturesque setting perfect for a serene getaway.
  • Caravan Parks: A unique choice for adventurous travelers, offering a communal atmosphere and the chance to enjoy the outdoors.
  • House Boats: Experience a one-of-a-kind stay on the water, combining comfort with stunning views of Southold's landscape.**

Top attractions in Town of Southold Town

Southold Town, New York, is a perfect destination for outdoor enthusiasts and romantics alike. Explore beautiful beaches, scenic parks, and charming farms. Enjoy paddleboarding at the local beaches, take in stunning views, and capture memorable photos of the coastline. With attractions that cater to those seeking culture and outdoor experiences, Southold Town promises a delightful vacation filled with relaxation and adventure.

  1. Orient Point County Park: This urban park offers a perfect blend of family-friendly activities and outdoor adventures, featuring picturesque views of the Long Island Sound and opportunities for picnicking and hiking amidst lush landscapes.
  2. 67 Steps Beach: A charming beach that invites relaxation and sunbathing, characterized by its unique 67 steps leading down to the sandy shore, making it a delightful spot for beachgoers to enjoy the sun and surf.
  3. Harbes Family Farm: A vibrant farm experience with seasonal activities, including berry picking, hayrides, and a market offering fresh produce and local goods, perfect for families and nature lovers alike.

Things to do recommended for couples

For a romantic getaway in Southold Town, visit Kontokosta Winery, Macari Vineyards, or Raphael Winery. Each offers a charming atmosphere with delightful wines and entertainment, perfect for couples looking to enjoy beautiful views and create lasting memories together.

Things to do recommended for families

While in Southold Town, families can delight in a ride on the charming Greenport Carousel, offering outdoor fun for all ages. Afterwards, unwind at Goldsmith's Inlet Park, a serene recreational area perfect for relaxation and wellness activities, making for a fantastic family day out.

Things to do recommended for groups

Experience the scenic Island's End Golf and Country Club for a fun day of golf, then visit the vibrant Greenport Farmers' Market to explore local produce and crafts. Enjoy the outdoors and connect with fellow travelers in the charming atmosphere of Southold Town.

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

When planning your trip—whether you're traveling with a group, family, or pets, or seeking extended stays—it's essential to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Town of Southold Town with a group: Take into account how many bedrooms you require, as well as features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Town of Southold Town with young kids: Traveling with young kids can present its own set of challenges. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions can make a big difference in your experience.
  • Taking your pets with you to Town of Southold Town: For many families, a vacation isn't truly fulfilling unless their furry companion is along for the ride. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Town of Southold Town: If you're seeking vacation 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 rental options. 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 in Town of Southold Town

Town of Southold Town offers a picturesque getaway perfect for outdoor lovers and romantics alike. Explore the charming town beaches, where you can unwind in a beach paradise setting. Enjoy sunny weather and family-friendly excursions surrounded by stunning scenery. Whether you're seeking relaxation or adventure, the sizable Town of Southold provides a delightful atmosphere that captures the essence of a perfect vacation destination.

  • Greenport: Nestled along the North Fork of Long Island, Greenport is a charming waterfront village that offers a delightful blend of outdoor activities and romantic experiences. Known for its picturesque marina and vibrant arts scene, visitors can enjoy a stroll along the scenic harbor. Popular attractions include local beaches perfect for family outings, as well as a variety of golf courses and resorts nearby. Greenport is also home to a lively downtown area filled with unique shops, restaurants, and cafes, making it an ideal spot for both relaxation and adventure.
  • Southold: Southold, a serene town rich in history, is a haven for outdoor enthusiasts and those seeking romantic escapades. This inviting area features beautiful beaches and tranquil lakes, perfect for swimming, picnicking, or simply soaking up the sun. Visitors can explore recreational areas and enjoy seasonal activities such as skiing in the winter months. The local charm is enhanced by quaint shops and eateries that reflect the town's heritage, ensuring a fulfilling travel experience for families and couples alike.
  • Mattituck: Mattituck is a delightful town known for its agricultural roots and vibrant market scene. This area is ideal for outdoor lovers, offering a mix of recreational activities such as golfing and visiting public markets where you can find fresh local produce. Families will appreciate the beautiful beaches and lakes, which provide ample opportunities for fun in the sun. With its friendly atmosphere and proximity to other attractions on the North Fork, Mattituck is a great destination for a leisurely getaway.

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? 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 aligns with your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. Being the organizer certainly has its perks! Become part of our One Key rewards program to unlock exclusive savings for members and start accumulating OneKeyCash™ on eligible stays. Sign up now and begin your journey to savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board is a fantastic tool that allows you to easily create new trips, pick up right where you left off, and manage your travel plans with ease. You can find any properties you've saved or booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Southold Town: family memories are made here

Southold Town lies along the furthermost tip of Long Island, around 100 miles east of New York City. It's long been a getaway destination for families from the Big Apple and while it may not have the glitz and glam of the nearby Hamptons, it's got a wealth of things to do nonetheless. It doesn't matter if you're a beach bum, foodie or adventure nut, you'll find everything you need near your Southold Town vacation rental. Top that with some family-friendly attractions, some quaint town festivities and a few wineries, and you've just found your new summer hotspot.

Star gazing in Southold

There are several points of interest near your Southold Town vacation rental that warrant time away from your beach towel. Don't know your Orion from your Big Dipper? At the Custer Institute and Observatory, Long Island's oldest observatory, you can take in the starry night sky and learn about the constellations. Alternatively, take a visit to the Horton Point Lighthouse, which has been keeping passing ships safe since the mid-19th century, or learn about the native Indians which once inhabited Long Island and view an impressive collection of arrowheads and other artifacts from those days.

Sail the Long Island coast from Southold Town

Southold Town is where family adventures are made. If you've brought the kids, they'll love the water-based activities, which range from sea kayaking to sailing. Alternatively, you can dive into a fishing store for bait and try your hand at reeling in supper to take back to your Southold vacation rental. Coastal hiking is always popular, as is cycling along the country lanes. There are seasonal activities too. In late summer, you can swing by one of the local fruit or vegetable farms with the little ones, to get them picking their own produce.

Highly changeable weather in Southold Town

Your stay in a Southold Town can be drastically different depending on the time of year that you visit. During summertime, families escape stuffy New York City and head 100 miles east to Long Island for time by the sea. It's certainly the hottest time to visit but also the most crowded. While the shoulder seasons might be a little cooler, that's the only sacrifice you'll have to make in return for a quieter vacation and a dip in rental prices. Winter sees Southold deserted by travelers, but the dramatic weather can be wonderful in your cozy Southold Town vacation rental.

Exploring the natural landscape of Town of Southold Town

Whether you're an adventurous traveler or just want to appreciate the scenery, Town of Southold Town is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Sunset Beach (3.3 mi / 5.4 km)
  • 67 Steps Beach (4.9 mi / 7.9 km)
  • Sag Harbor Marine Park (8.3 mi / 13.4 km)
  • Orient Beach State Park (9.6 mi / 15.4 km)
  • The Hamptons Beaches (11.8 mi / 19 km)
  • Orient Point County Park (11.8 mi / 19 km)

Transportation options to and around Town of Southold Town

Fly into Fishers Island, NY (FID-Elizabeth Field), the closest airport, located 24.5 mi (39.4 km) from the city center.

If you're traveling by train, Southold Station, Greenport Station and Mattituck Station are the main stations in the area.

Frequently asked questions

What is the best area to stay in Town of Southold Town when booking a vacation rental?
If you’re on you way to Town of Southold Town, Greenport West is among the most sought-after locations to stay. Whatever your style of travel, Vrbo is bound to have a vacation property here that’s right for you.
What is the most popular type of vacation rental accommodation in Town of Southold Town?
Based on our research, cottages are considered the most popular type of property in Town of Southold Town. But as you might expect, everyone’s idea of an epic stay differs. Vrbo has vacation rentals in a variety of sizes and shapes, so you’re sure to find the perfect fit.
How much does it cost to rent a vacation rental in Town of Southold Town?
The average price for a vacation home in Town of Southold Town depends on a number of factors, including property type, season and length of stay. Whether you’re dreaming about a sprawling house with room for friends and family or a quaint cabin for just you and your sweetheart, just enter your dates of travel to discover stays with great value.
How much does it cost to rent a beach house in Town of Southold Town?
The average price for a vacation rental near the beach in Town of Southold Town depends on when you’ll be there and the style and size of property you’re searching for. You can easily and quickly find prices on Vrbo by entering your preferred travel dates. Then use our filter tool to select the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Town of Southold Town?
With 512 properties that welcome pets, your happy hound can join you on your Town of Southold Town break. Use our filter tool to search our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
Can I rent a house with a pool in Town of Southold Town?
Add a new level of fun to your vacation by booking your group into one of the 156 houses with a private pool in Town of Southold Town. Use our search filter to find properties with pools on Vrbo, then spend leisurely days splashing about in a swimming pool that’s for your use only.
What are popular rental amenities in Town of Southold Town?
Some of the most popular rental amenities people are searching for in Town of Southold Town include a fireplace, an electric car charging station and a beach view. Whether you’re vacationing with your besties, family or even pets, Vrbo vacation homes feature the best amenities for starting a new adventure with the people you cherish the most.
Are there large group vacation rentals in Town of Southold Town?
Town of Southold Town has 96 vacation rentals that can cater to 10 or more guests. These properties come with the privacy and space you need to share good times with your favorite people.
Are there vacation rentals in Town of Southold Town that welcome kids?
Gather your whole family for an adventure in Town of Southold Town at one of our 503 family-friendly vacation rentals. Many of these stays feature amenities that are perfect for getaways with the little ones, like full kitchens, extra bedrooms and private pools. Simply check the “Properties good for families” filter box and decide on your favorite.
What are the top attractions for families in Town of Southold Town?
There are loads of awesome things to do and see with the family in Town of Southold Town, such as:

  • Goldsmith’s Inlet Park
  • Camera Obscura
  • Railroad Museum of Long Island

Are there one-bedroom vacation rentals in Town of Southold Town?
You’ll find 32 one-bedroom properties in Town of Southold Town to pick from. A one-bedroom vacation rental is a great option if it’s only the two of you or if you’re traveling alone. Add in more space, convenience and privacy than a standard hotel, and you’ve got the makings of a break to remember.
Can I find two-bedroom vacation rentals in Town of Southold Town?
You can select from 99 two-bedroom properties in Town of Southold Town. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There’s space for whoever’s fortunate enough to be coming along for the ride.
Are there vacation rentals with WiFi in Town of Southold Town?
Town of Southold Town has 226 vacation rentals with WiFi, so you’ll be able to stay connected while you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with your family to catching up on social media, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Town of Southold Town?
Town of Southold Town has 491 vacation rentals where you’ll be able to relax in air-conditioned comfort. To find a stay on Vrbo that features this amenity, enter your desired travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Town of Southold Town?
The minimum age is generally 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your chosen Town of Southold Town vacation rental before making a booking.
How long can I rent a vacation rental in Town of Southold Town for?
It’s down to the Town of Southold Town property. To look at a list of options offering extended stays, just enter your travel dates and number of people into Vrbo’s search page. Look forward to having the property to yourself, along with the comforts of home like air conditioning, a kitchen and outdoor spaces where the kids can burn off energy. Keep an eye out for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Town of Southold Town?
Weekend retreat or extended escape, Vrbo has some fantastic deals and discounts in Town of Southold Town to match your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — without breaking the bank.

Explore destinations around Town of Southold Town

More Vacation Rentals ideas

People also search for