Sag Harbor, NY, USA

Sag Harbor, NY, USA

We found 2,219 vacation rentals — enter your dates for availability


Find the best place to stay — Sag Harbor

Where to stay around Sag Harbor, NY?

Our 2018 property listings offer a large selection of 2,219 vacation rentals near Sag Harbor. From 1,903 houses to 132 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Sag Harbor for a holiday or a weekend are on HomeAway.

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.

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.

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.

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.

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.