With origins dating back to the 1700s, Sag Harbor is a small village in New York that lies between Southampton and East Hampton. It was a prosperous harbor and the first commercial port in the United States, and most of Sag Harbor is on the National Register of Historic Places, making it a charming place to visit – especially for history buffs.
Start your trip by stopping in the windmill by the harbor, which is where the visitor center is located. Main Street is the center point of the town and home to many small town-style shops and restaurants, as well as the location for many different fairs, festivals, and other events going on in the town. The Sag Harbor Whaling and Historical Museum is located on Main Street and was originally the home of Benjamin Huntting II, a leading citizen of the town who owned whaling ships and made his fortune off the whale oil brought home on his ships. The museum houses lots of artifacts from Sag Harbor’s old whaling days, is open seven days a week from 10am to 5pm and costs $6 for adults. For those looking to spend some time out on the water, Sag Harbor Sailing offers sailing classes, rents out boats, and hosts fishing charters. Bay Street Theater was founded in 1991 and is a non-profit professional theater and community cultural center that offers year-round entertainment, and many of the shows that have premiered here have made it to Broadway and Off-Broadway. Lie out in the sun at Foster Memorial Beach, a mile-long beach on Noyac Bay that includes dog-friendly walking routes. Other cools sites to check out include the Elizabeth A. Morton National Wildlife Refuge, which is home to diverse habitats and hiking trails, as well as Big Olaf, a local ice cream shop that keeps residents and visitors coming in to try all of the different flavors on the menu.
Due to its central location, Sag Harbor is surrounded by plenty of other beach towns that make for great day trips. They include North Haven, Southampton, East Hampton, and Amagansett, which are all a short drive by car. Shelter Island, which is at the eastern end of Long Island, makes for another great weekend escape and offers lots of outdoor water activities, from paddleboard rentals and a local craft brewery to a beautiful nature farm.
There are many great rental options, from beach cottages to large historic homes. If you want to be close to where everything is happening in Sag Harbor, you may want to book a rental near Main Street, which is the central point of the town. There are also several great coastal suburban neighborhoods to stay in such as Noyack, Wainscott and Northwest Harbor. Noyack is located just west of Sag Harbor, Northwest Harbor is east of Cedar Point County Park, while Wainscott is south of Sag Harbor by the water.
A rental car is the most convenient way to get around Sag Harbor, but many locals and visitors use the Suffolk County Transit Bus System, which offers numerous routes that include stops in East Hampton, Bridgehampton, Three Mile Harbor, and other nearby towns. You can also rent a bicycle or stroll through the charming parts of town like Main Street.
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Search properties from 11 rental sites in Sag Harbor where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 1,194 HomeAway rentals, 167 TripAdvisor short term rentals and 107 Booking.com vacation rentals.