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Vacation rentals in Montauk

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Top-rated vacation rentals in Montauk

Guests agree: these stays are highly rated for location, cleanliness, and more.

New! Hamptons Sag Harbor Village Pool& Beach House
SUPERHOST
Entire house · 8 guests · 6 beds · 2 baths

New! Hamptons Sag Harbor Village Pool& Beach HouseNew, immaculate, all-season home by the beach with crisp designer details. Every detail was considered for maximum enjoyment. The large heated pool (open April-Oct) hot tub & deck gets sun all day. Located in the village of Sag Harbor, steps from the Bay and Main Street & all the Hamptons has to offer. Come feel the vacation vibes as soon as you walk through the door. The central location, luxurious finishes, year-round breathtaking sunsets on the sandy beach make this the perfect getaway.

Walk to it all! - Eat, Drink, Beach, Shop - Apt #1
SUPERHOST
Entire house · 6 guests · 3 beds · 1 bath

Walk to it all! - Eat, Drink, Beach, Shop - Apt #1Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Designer East Hampton Farmhouse
SUPERHOST
Entire house · 8 guests · 4 beds · 2.5 baths

Designer East Hampton FarmhouseStylish, newly renovated three bedroom, two and a half bath cottage built around the turn of the century and moved from the beach in Amagansett to its current location just outside of town. Completely renovated in 2018. Located five minutes from East Hampton Village, Amagansett Village, Springs and Ocean Beaches. Perfect for families with young children!

Vacation rentals for every style

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Popular amenities for Montauk vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Montauk

SUPERHOST
  1. Entire apartment
  2. Montauk
Montauk Beach Bungalow West
$271 per night
SUPERHOST
  1. Entire house
  2. Sag Harbor
Sag Harbor home away from home
$355 per night
SUPERHOST
  1. Entire condominium
  2. Montauk
Montauk Waterfront Condo w/ Sunset Views
$282 per night
SUPERHOST
  1. Entire cottage
  2. Montauk
Waterfront Cottage, Montauk
$400 per night
SUPERHOST
  1. Entire house
  2. Greenport
Greenport Village Retreat. Walk to it All - Apt #1
$256 per night
SUPERHOST
  1. Entire cottage
  2. Montauk
Montauk Oceanview Cottage
$260 per night
SUPERHOST
  1. Entire cottage
  2. Montauk
Montauk Oceanview
$300 per night
SUPERHOST
  1. Entire condominium
  2. Montauk
Deluxe StudIo Apt@The Montauk Manor
$111 per night
SUPERHOST
  1. Entire cottage
  2. Sag Harbor
Eden, your ideal beach retreat
$482 per night
SUPERHOST
  1. Entire cottage
  2. Montauk
Work from a Modern Montauk Cottage - Reduced!
$189 per night
SUPERHOST
  1. Entire cottage
  2. Montauk
Waterfront Cottage, Fort Pond MTK
$400 per night
SUPERHOST
  1. Entire cottage
  2. East Hampton
Carriage House - Cottage in East Hampton Village
$249 per night

All About Montauk

For more than 4,000 years, the Montaukett Native Americans lived on these lands — hunting, fishing, and farming cattle and sheep. They used what is now Ditch Plains Beach as a lookout point, since the surrounding moorlands kept the beach hidden until it’s seen at the edge of the cliff. It’s from the Montaukett name that the hamlet of Montauk got its name. These days, locals tend to refer to the area as “The End,” since there is no land point beyond its borders. But with 5,000 acres of beach and parklands, getting to Montauk is simply the beginning of endless outdoor adventures.

How do I get around Montauk?

Whether you prefer planes, trains, automobiles — or bus or ferry — getting to Montauk means simply heading as far east on Long Island as you can get from New York City. Drivers can make the 120-mile trip from Manhattan by taking 495 East to Exit 70 for Manorville Road. From there, it’s south to Sunrise Highway (also known as Route 27) for the final 50 miles, passing through Bridgehampton, East Hampton, and Amagansett along the way. (It’s also 20 miles from Sag Harbor and 27 miles from Shelter Island.) Pack your patience, as the single throughway can get crowded on popular weekends, particularly in the summer. A jitney bus and the Long Island Railroad also provide service from Manhattan. The private Montauk Airport (MTP) has flights to New England destinations, including Rhode Island’s Block Island, while the Long Island MacArthur Airport (ISP) in Ronkonkoma offers more options, but is 70 miles away. Car and passenger ferries also run from New London, Connecticut.

When is the best time to book a Montauk vacation rental?

The warm summer days serve as a magnet for weekenders looking to don their chicest beachwear and bask in the comfortable temperatures in the 60s and 70s Fahrenheit. Winters hover in the upper 20s to mid-40s, so travelers generally stay away during the short days, since it isn’t just cold, but rainy and windy too. Fall and spring can range from the upper 30s to upper 60s, but it’s still no match for the peak outdoor season from mid-June to late September. As a peninsula surrounded by the Atlantic Ocean and Block Island Sound, the ocean breeze can be strong at times, so a windbreaker or light jacket is recommended, even on sunny days.

What are the top things to do in Montauk?

Ditch Plains Beach

The further east you go in Long Island, the bigger the waves get. As the easternmost point, Ditch Plains is best known for its incredible surfing conditions. But sunbathers, swimmers, and dog walkers also frequent the lifeguarded beach.

Hither Hills State Park

The 1,755-acre park has a two-mile ocean beach, a 190-site campground, and a 40-acre freshwater lake for fishing, as well as a trail through the walking dunes.

Montauk Lighthouse Museum

At the tip of the peninsula is New York state’s oldest lighthouse, authorized under George Washington in 1792 and completed in 1796 — and still in use today. There are 137 iron steps to the top of the 110-foot tower, and the lights, which flash every five seconds, can be seen up to 19 nautical miles away.

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