Where to stay around Town of Southold Town?

Our 2018 property listings offer a large selection of 3,253 vacation rentals near Town of Southold Town. From 2,621 Houses to 329 Bungalows, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best places to stay near Town of Southold Town are on HomeAway.

What is the best area to stay when traveling to Town of Southold Town?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Town of Southold Town:

  • Pipes Cove: 51 vacation rentals
  • Mystic: 100 vacation rentals
  • Niantic: 32 vacation rentals
  • Mason's Island: 24 vacation rentals
  • Clearwater Beach: 100 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Town of Southold Town?

HomeAway offers a large selection of vacation rentals near lovely places in Town of Southold Town. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Orient Point County Park: 2,902 vacation rentals
  • Railroad Museum of Long Island: 3,034 vacation rentals
  • Orient Beach State Park: 3,083 vacation rentals
  • Goldsmith's Inlet Park: 3,111 vacation rentals
  • Bedell Cellars: 3,127 vacation rentals

But there are many other points of interest around Town of Southold Town listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Town of Southold Town?

Yes, of course. HomeAway has 2,621 Houses in Town of Southold Town. Our other popular types of vacation rentals in Town of Southold Town include:

  • Bungalows: 329 rentals available
  • Cabins: 329 rentals available
  • Cottages: 329 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I rent waterfront rentals in Town of Southold Town?

Absolutely, HomeAway has 489 waterfront rentals in Town of Southold Town. You have also many other possibilities in Town of Southold Town area, including:

  • Golf course rentals: 480 rentals
  • Village rentals: 480 rentals
  • Beach view rentals: 313 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with kids' high chair in Town of Southold Town?

Yes, you can select your preferred vacation rental with kids' high chair among our 342 vacation rentals with kids' high chair available in Town of Southold Town. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    Spot ospreys in Southold Town

    Nestled along miles of shoreline on nearby Shelter Island, the Mashomack Preserve has one of the densest wildlife populations in the north-east. The preserve has been part of the Nature Conservancy since 1980 and takes up more than 2,000 acres and more than a 1/3 of the island. Its forest, marshland and tidal creeks provide habitats for many birds, but the highlight is sightings of nesting ospreys, one of the largest populations along the East Coast, along with piping plovers and terns. The calm salt marshes also serve as an important breeding ground for young marine life.