Discover a selection of 2,000 vacation rentals in Sag Harbor, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $300 per night, and houses and cottages are popular options for a stay in Sag Harbor. Either way, you'll find a rental for everyone's needs.
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Destination guide

Sag Harbor oozes charm and offers sweeping views

Tucked away in Suffolk County, Sag Harbor is one of New York’s best kept secrets. Locals love to refer to it as the insider’s alternative to the more stuffy Hamptons villages, and it’s easy to see why. The laid-back former whaling town is dotted with beautifully restored historic homes, offering sweeping views over Peconic Bay. To experience the town like a local, swap a run of the mill hotel for a characterful Sag Harbor vacation rental. The seaside community may be small, but it serves up an inspired dining scene, covering everything from freshly caught seafood to artisan ice cream.

Things to do

Soak up 300 years of Sag Harbor history

Housed in a 19th-century mansion, the Sag Harbor Whaling Museum offers a gruesome glimpse at the town’s seafaring past. As well as whaling, Sag Harbor was one of America’s first commercial ports – find out more at the Custom House Museum. If you’re staying the night, catching a show at the historic Bay Street Theatre or Art Deco Sag Harbor Cinema is a great way to wind up a day of sightseeing. Want to stay close to the action? Check out Sag Harbor vacation rentals for a colorful selection of unique properties, just steps from the town center.

Activities

Slow down the pace in Sag Harbor

Sag Harbor is steeped in history, and one of the best ways to soak it all up is on a walking tour of the town. Pick up a map from the Chamber of Commerce, and spend a few hours admiring historic homes, exploring the harbor, and sifting through antique stores. For something a little more upbeat, why not sign up for a sailing class, private charter, or catamaran cruise? Thanks to its calm bay, water sports are big in Sag Harbor. You could rent a paddle board, zoom around on a jet ski, or try your luck at flyboarding.

Weather

Summer sunshine in the Hamptons

Traditionally, sunseekers flock to Sag Harbor from Memorial Day through to Labor Day. The weather is beautiful, the ocean is calm, and the days are luxuriously long. If you’re not keen on crowded beaches, Sag Harbor vacation rentals are the perfect way to secure a private pool and soak up the Long Island sunshine. Sag Harbor starts to empty out come September, and while it may be a little colder, early fall is still a fantastic time to enjoy the unique charms of the Hamptons.

Natural features

Beaches, bike trails, and world class wineries

Sandwiched between the villages of East Hampton and Southampton, Sag Harbor is one of several seaside communities that make up the prestigious Hamptons strip. Overlooking Peconic Bay, the harbor is well protected from the wind, waves, and wild weather of the Atlantic Ocean. Spend the day beach hopping, or rent a car and work your way through Long Island’s famous North Fork winery trail. If you’re craving fresh air, why not explore Sag Harbor on 2 wheels? Winding through pine forests, horse ranches, and beachfronts, Sag Harbor cycling routes are seriously picturesque. Wash it all down with a post-pedal brunch at a farm-to-table restaurant.

How to get there

How to get to and around Sag Harbor

Fly into East Hampton, NY (HTO), the closest airport, located 4.5 mi (7.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Westhampton, NY (FOK-Francis S. Gabreski), which is 19.7 mi (31.8 km) away.

How many vacation rentals are available around Sag Harbor, NY?

Our 2020 property listings offer a large selection of 1,913 vacation rentals around Sag Harbor. From 1,813 house rentals to 105 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Sag Harbor?

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 Sag Harbor:

  • Westbrook Center: 55 vacation rentals
  • Saybrook Manor: 34 vacation rentals
  • Old Saybrook Center: 16 vacation rentals
  • East Hampton North: 284 vacation rentals
  • Clearwater Beach: 97 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Sag Harbor?

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

  • Sag Harbor Marine Park: 2,671 vacation rentals
  • Bay Street Theatre: 2,661 vacation rentals
  • Sag Harbor Old Burying Ground: 2,663 vacation rentals
  • Sag Harbor Whaling and Historical Museum: 2,650 vacation rentals
  • Old Whaler's Church: 2,665 vacation rentals

But there are many other points of interest around Sag Harbor listed on Vrbo 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 Sag Harbor?

Yes, of course. Vrbo has 1,813 Houses in Sag Harbor. Our other popular types of vacation rentals in Sag Harbor include:

  • Cottages: 105 rentals available
  • Condos/Apartments: 32 rentals available
  • Bungalows: 105 rentals available

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

Can I find a vacation rental with pool in Sag Harbor?

Yes, you can select your preferred vacation rental with pool among our 1,307 vacation rentals with pool available in Sag Harbor. Please use our search bar to access the selection of vacation rentals available.

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