4 Trending Rentals in New York That People Book on Repeat (And We See Why)

The state of New York is known for its historic landmarks, state parks, museums, cultural institutions, unique tours, excursions, and its renowned entertainment industry. There’s truly something for everyone in New York. While many seek the thrill of the bright lights and excitement in New York City, New York is also home to towns and communities that are perfect for those seeking calm, nature-filled vacation stays, near beaches, farms, mountains, and shopping destinations that are easily accessible. Below are four exemplary vacation rentals that guests absolutely love, and we totally understand why!

1. Modern Beach House-Montauk

I have to admit that I love a luxurious beach vacation, even when traveling with my family and kids. This modern and chic beach house is within walking distance of Ditch Plains Beach, and it’s a perfect stay for large families, families with kids of differing age groups, and even singles who may want a larger space for special occasions like a bachelorette or bachelor party. And, while the place is high-end, there are kid and teen-friendly amenities like beach cruisers, surfboards, surfboard storage, and even a large beach wagon for toting around the little ones. With its open loft-style design, private home office, chef’s kitchen, and plenty of outdoor eating space, it’s great for cookouts and communal gatherings, and has lots of private space for adults, too. And, if surfing and the beach are not quite your jam, the property is located right next to a nature preserve, which is perfect for scenic nature walks.

2. Chic Barn House-Sag Harbor

Sag Harbor is known for its beautiful real estate, and the vacation rentals live up to the town’s reputation as well. This stunning 3,800 sq. ft. Sag Harbor retreat combines modern barn-style architecture with luxurious amenities, including a heated swimming pool, spa, and expansive outdoor living spaces. Just steps from a private Bay Beach and historic downtown, the home offers five bedrooms, seven and a half baths, a Poggenpohl kitchen, and an elegant open-concept design for an unforgettable and relaxing experience. 

While Sag Harbor has become synonymous with gorgeous beaches, top-knotch shopping boutiques, and cozy, posh restaurants, the land and surrounding neighborhoods are rich in history, too. And, for those seeking to venture away from this lovely oasis (Did I mention that the main bedroom has a sundeck?), you may want to take a tour through Sag Harbor’s Eastville Heritage House, take a tour of Sag Harbor’s historical communities, visit the Cedar Island Lighthouse, or learn something new at the Sag Harbor Historical Museum.

3. Private Villa With Views of the Hudson River-Highland 

Highland is known for its scenic views of the river, quaint eateries, hiking, farms, state parks, and historical landmarks such as the Walkway Over the Hudson. Highland is a peaceful and serene community surrounded by nature. This stunning, isolated villa sits on a 200-foot granite bluff overlooking the Hudson River, offering privacy and panoramic 70-mile views of the river, along with world-class amenities including a heated saltwater pool, hot tub, sauna, and even a lighted tennis court. The property has four ensuite bedrooms, a gourmet kitchen, a media room, and an expansive riverside deck. It's perfect for nature-lovers who can truly appreciate a great view, embrace isolation and solitude, and are looking for a vacation rental that feels like an oasis in nature.

4. Adirondack Luxury Lake Estate-Remsen

There’s nothing like being at a beautiful lake property surrounded by the ones you love. Not only is this lake estate located 150 feet above Hinckley Lake, but there’s a large pool that families will truly appreciate. And, while the scenic mountain landscape is perfect for a cozy romantic getaway for adults, there are plenty of amenities that kids and teens will definitely appreciate, like arcade video game machines, an oversized pool table, a hot tub, and even a garden and lanai. And, a large communal-sized table for large family gatherings. Also, there’s lots to do in the Adirondacks, like historic sites, kayaking, boating, ziplining, winter carnivals, and go sightseeing at the waterfalls, and visit museums like The Wild Center in the Adirondacks.

With fantastic reviews, one-of-a-kind rental options, and lots of opportunities for adventure and exploration, it’s evident that New York aims to make your vacation experience extra special. These properties are booked on repeat, so be sure to book your stay well in advance! Feeling inspired? Be sure to use the Only In Your State Itinerary Planner to create your customized vacation for your next visit to New York!