Discover a selection of 2,500 vacation rentals in Sag Harbor 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 kitchens. Prices start at $458 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?

Our 2020 property listings offer a large selection of 2,287 vacation rentals around Sag Harbor. From 2,036 house rentals to 129 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a seaside property in Sag Harbor?

Perhaps it's the spectacular sea views, or maybe it's the opportunity to just bliss out all day, every day. There's just something about a beach getaway that appeals to one and all. There are 682 beachside vacation homes to choose from. Of course, that might not suit everyone. Fortunately, Vrbo has oodles more options, including:

  • 455 village vacation rentals.
  • 264 beach vacation rentals.
  • 260 water-view vacation rentals.

Can I rent a house in Sag Harbor?

Instead of booking a cookie-cutter hotel room this vacation, you could just go for an entire house. You'll be a part of the neighborhood before you know it! There are 2,078 houses currently listed on Vrbo. Prices start at $67 per night. Or perhaps you'd rather one of the area's other lodging options, like:

  • Cottage: 129 vacation homes. Prices start from $100 per night.
  • Farmhouse: 30 vacation homes. Prices start from $193 per night.
  • Estate: 27 vacation homes. Prices start from $432 per night.

Can I stay in Sag Harbor in a large group?

Whether you're going on a break with the extended fam or spending a week away with your old school mates, it's always stacks of fun hanging out under the same roof! And the great news is that Vrbo has options to suit you. House vacation homes are the most popular option here for big groups of travelers. Our extensive database currently has 651 available. If you're wanting to stay in a big group, the rental properties that will serve you well include:

  • Are you looking for vacation homes that can hold 8 people? We have 691 that will be ideal. The prices start from $199 per night.
  • After a vacation property for 6 guests? We have 528 that will suit. Prices begin at just $150 per night.
  • Seeking rentals to suit 10 guests? You'll be delighted to find out we have 356 that'll be ideal. You can secure one for as little as $256 a night.

You and your posse will be in good hands when you plan your Sag Harbor getaway through us!

Where are the cheapest rentals in Sag Harbor?

Those cramped hotel rooms are no place to spend those precious vacation moments! Explore our reasonably priced rentals now and ensure everyone in your crew has room to move. Old Saybrook Center is a great area to have a look at if you want to keep an eye on your budget. Vrbo has 29 rentals, and the average price is a modest $271 per night. Saybrook Manor is another good option. We've got 36 rentals here, and the average price is around $272 a night.

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