Town of Southold Town Vacation Rentals, New York: Whole House to Yourself

Select from 428 homes, 64 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.

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Beautiful spot on the #longisland sound surfing

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Gorgeous private Hamptons house with pool and volleyball court

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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?

Greenport West is among the most in-demand locations to book a vacation property in Town of Southold Town. Stay here and delight in the privacy and convenience that comes with having the whole place to yourself.

What is the most popular type of vacation rental accommodation in Town of Southold Town?

Houses are the most popular style of vacation rental in Town of Southold Town, according to our data. Even if you've got something else in mind, Vrbo has properties in many shapes and sizes. Browse our many options to find your ideal match.

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 is determined by several factors, including property type, season and length of stay. Whether you're looking for a sprawling villa with space for extended family or a cozy cabin for you and your other half, just enter your travel dates to view stays with unbeatable value.

How much does it cost to rent a beach house in Town of Southold Town?

The average price for a vacation home close to the beach in Town of Southold Town will depend on when you're going and the size and style of property you're searching for. Find prices easily and quickly on Vrbo by entering the dates you'll be traveling. Then use the filter tool to choose the number of bedrooms and amenities that you prefer, like WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Town of Southold Town?

Pack a bone and a squeezy toy for your canine companion because Town of Southold Town has 483 properties that roll out the welcome mat to doggie guests. Let your furriest pal join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check our "Pets allowed" filter box.

Can I rent a house with a pool in Town of Southold Town?

Pack your swimsuit and inflatable swan, because there are 140 houses with a private pool in Town of Southold Town. Make a booking at one of these popular vacation homes and make every day a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Town of Southold Town?

The most popular rental amenities people search for in Town of Southold Town are an electric car charging station, tennis and a fireplace. Whether you're hitting the road with buddies, family or even pets, Vrbo vacation homes come with the best amenities for fun and relaxation with the people that matter most.

Are there large group vacation rentals in Town of Southold Town?

With 83 vacation rentals that can host 10 guests or more in Town of Southold Town, there's no need to keep your invite list short. From fun family get-togethers to special events like Thanksgiving or Christmas parties, Vrbo can help you find a large group rental that fits the occasion.

Are there vacation rentals in Town of Southold Town that welcome kids?

With 478 family-friendly vacation homes to select from in Town of Southold Town, there's never been a better time to introduce the kiddos to the thrills of travel. Just click on our "Properties good for families" filter box to find stays that come with conveniences ideal for vacationing families, such as dining rooms, yards, bunk beds and hot tubs.

What are the top attractions for families in Town of Southold Town?

Keeping the kids entertained during your vacation in Town of Southold Town is a cinch with these leading family-friendly attractions:

67 Steps Beach
Railroad Museum of Long Island
Crescent Beach

Are there one-bedroom vacation rentals in Town of Southold Town?

Yes, you'll find 28 one-bedroom properties in Town of Southold Town to select from. A one-bedroom vacation rental is a wonderful choice if it's just you and your partner or if you're flying solo. Throw in more convenience, space and privacy than a hotel, and you'll be sure to have a memorable trip.

Can I find two-bedroom vacation rentals in Town of Southold Town?

Town of Southold Town has 94 two-bedroom vacation rentals to choose from. Enjoy a vacation home with all the comfort and privacy you're looking for at an attractive price on Vrbo.