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I Stayed At A 99-year-old Hotel In Montauk For $490. It Hasn't Lost Any Of Its 1920s Charm.

Montauk Manor was completed in 1926.

Jonah Rosenberg for Business Insider

Montauk Manor has been a Hamptons institution since it opened its doors in 1926.
During my stay in August, I was impressed by its modern amenities and historic architecture.
In the nearly 100 years since it opened, it hasn't lost any of its '20s charm.

Just over 100 miles East of New York City lies Montauk, the easternmost tip of Long Island, and a playground for the East Coast's wealthy.

It wasn't always that way. Montauk was founded in 1648, and for centuries, it was a relatively sleepy fishing village, and later, a sleepy surfing town. But that all began to change when a developer named Carl G. Fisher, the man responsible for building up Miami Beach, set his sights on Montauk.

He planned to make the area the "Miami of the North," and bought some 9,000 acres of land to make that dream a reality in the early 1920s. Fisher's pièce de résistance was Montauk Manor, a hotel atop Signal Hill.

Now, almost 100 years later, his plan seems to have worked, for the most part. Montauk is just as crowded as the Hamptons every summer, and his hotel remains open. It was even added to the National Register of Historic Places in 1984.

Here's what it's like to stay in Montauk Manor during the town's busiest season.

I spent a night in Montauk Manor, a historic resort hotel on the easternmost tip of Long Island.

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Montauk Manor is one of the oldest hotels in Montauk. Ever since I was a kid visiting Montauk, I can remember seeing it on top of the hill, looking like the tallest structure in the town.

But I've never stayed there, so when the opportunity arose to check it out, I jumped at it.

The hotel sits atop one of Montauk's highest points, offering guests a view of the Long Island Sound and Fort Pond.

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From the outside, it almost looks like a very large Tudor-style house. But it's actually a four-floor, 140-room hotel with plenty of amenities inside, like a spa, a restaurant, conference rooms, an indoor pool, and a gym.

There's an outdoor lounge area right next to the entrance, where you can take in the views at all hours of the day.

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There was a volleyball net right in front of these chairs, but I never saw anyone using it.

In general, even though I went in August, it seemed relatively quiet at the hotel. It was never empty, but it wasn't overwhelmingly crowded. I think the property's large size had something to do with it.

The hotel was built in 1926, making it 99 years old.

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While there has been an ongoing restoration project of the facade by the architecture firm EDG, it really still feels like something out of another time, with all the trees and the classic Tudor Revival-style architecture.

Inside, the lobby was accented by exposed beams and multiple archways.

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The lobby ran across the entire westward side of the building. Chandeliers gave it a classy feel.

The decor had a vintage feel, down to the patterns of the couches.

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This print would not go with the millennial gray aesthetic that's become so popular in recent years.

There was a framed photo hanging in the lobby showing what the property used to look like when there were more buildings around.

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You might have noticed the barracks on the right side of this photo. This photo was taken during World War II, when, per The Montauk Library, the US Navy took over the hotel and used it as a base.

"You will, I know, share the pride that I feel in our beloved Manor, with its fine accommodations, climate, and setting, as it is proving at this time of national stress to be of real usefulness to our country," said the resort's manager at the time.

Montauk has been used by multiple armed forces over the years. An abandoned Air Force base was even the inspiration behind "Stranger Things."

The hotel was built by industrialist Carl Fisher and designed by an iconic architectural firm.

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Fisher knew what he was doing when he hired Schultze & Weaver, the architects behind The Biltmore hotel in Miami and The Breakers hotel in Palm Beach. The Biltmore is one of the most iconic hotels in the US, and has been featured in many films, including "Oppenheimer."

Fisher himself is an interesting figure in American history. PBS reported he's essentially responsible for turning Miami Beach into the tourist destination and real-estate mecca it is today. Fisher Island, one of the most exclusive neighborhoods in Miami, is even named after him.

After his success in Florida, he turned his sights northward and intended to make Montauk "a Miami for the summer."

While he successfully built Montauk Manor, the stock market crash in 1929 severely damaged his finances, and he wasn't able to complete his dream for Montauk, which would've included "a beach club, a yacht club, polo fields, a golf course, glass-enclosed tennis courts, a boardwalk extending for over half a mile along the ocean, a ranch, and health spa," per the hotel's website.

Montauk Manor operates as a condominium-style hotel, which means individual units are for sale for owners to then rent out themselves.

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There's even a real estate office in the lobby. I saw prices from $400,000 to $800,000, depending on the size of the unit.

I stayed in an executive studio on the third floor. It was $490 for one night, after taxes.

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That's the cheapest type of room at Montauk Manor. The most expensive room, a three-bedroom suite, can cost up to $1,027 a night, depending on whether it's a weekend or when you're going in the summer.

My room was light and simply furnished.

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My room was painted a light gray, so I wasn't totally free of "millennial gray," but I didn't mind. I liked the various pieces of art depicting starfish, ships, and the ocean.

The best part about it was the huge windows.

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I could've sat in the chair in the sunlight all day if I had the time.

The view was unbeatable. At night, I could see fireworks over the water.

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I had a great view of the Long Island Sound, the beach, and even the Montauk train station.

The studio also had a full kitchen.

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There was a dishwasher, an oven, a microwave, a refrigerator, a freezer, and multiple cabinets filled with plates, cups, and silverware.

In Montauk, not any water will do. We were provided with Voss bottles.

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Voss, as any water sommelier will tell you, is from Norway. The brand counts Kim Kardashian as a fan.

The bathroom was on the smaller side, but tidy. The nautical theme continued throughout.

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It was a pretty standard hotel bathroom. For $490 a night, I was expecting something a bit more upscale, but it was fine for just one night. I did appreciate the large counter space.

The room was filled with cute touches, like this postcard of the property tucked into my door.

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Along with this postcard, I received a welcome note from the owner of my unit, a guide of things to do in Montauk and the Hamptons, and there was even a guestbook to sign. It went back to 2023, and was filled with notes from happy customers promising to return.

After checking in, I took a walk around the grounds. Many of these rooms are actually duplexes and have up to three bedrooms.

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Montauk Manor is a U-shape, which means not every room can face the Long Island Sound, like these do.

The ground-floor units also each had their own patio with chairs and tables. They were a semi-private place to enjoy the views.

Around the corner on the left side the building were also multiple charcoal grills for anyone looking to barbecue.

There's an Italian restaurant on the property, Monte's at the Manor. The Monte family used to own another iconic Montauk spot: Gurney's.

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The Monte family purchased Gurney's for $200,000 in 1956. They owned it for over 50 years before selling it in 2013.

The restaurant's outdoor seating and fountain made me feel transported to Italy.

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I ate dinner at Monte's, and it was delicious. I ordered chicken parm for $34, which was easily enough for two people. I also got a small order of spaghetti with Monte's trademark sauce, which I would recommend.

After dinner, I took a walk. There are multiple benches and places to sit scattered around the grounds to relax.

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When the sun set, though, it got very dark. They could use some more lighting.

There's also an outdoor pool with many lounge chairs and umbrellas.

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I didn't get a chance to take a dip, but it looked quite inviting.

There's also an indoor pool and Jacuzzi in the basement.

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The spa is down here, too.

There are also multiple grass tennis courts on the property, something you barely see in NYC.

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It's much more common to see hard courts in New York City, even at the US Open. Grass is much rarer.

You could spend an entire day walking around the grounds and taking advantage of the amenities.

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The landscaping was impeccable.

Of course, there's an entire town to see at the bottom of the hill.

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There's no shortage of things to do, including the beach, the lighthouse, Montauk Brewery, multiple restaurants and bars, and hiking.

And if you need help getting there, the Montauk Manor shuttle will take you anywhere you need to go in town, including the beach.

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Finding parking at the beach can be a huge pain during the summer, but having a free ride can make all the difference. You can also schedule a pick-up to take you back to the hotel.

While the prices aren't cheap, they are in line with the rest of Montauk during the high season.

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There will always be discount options, but Montauk Manor is certainly more affordable than places like Gurney's or Marram.

I would recommend Montauk Manor to anyone looking to see what Montauk was like almost a century ago.

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The history of Montauk Manor sets it apart from many of the other hotels in the area, which are either newer or have been redone to the point of being unrecognizable.

The Manor, on the other hand, has combined modern amenities and decor in the actual rooms with the '20s charm of the architecture and vibes of the common spaces.

It wasn't cheap, but I would consider coming back during the offseason. Montauk Manor is open year-round, and I could see it being beautiful during the fall and very cozy during the winter.

But it was fun pretending to be a character on "Gossip Girl," even if just for one night.

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I Stayed At A 99-year-old Hotel In Montauk For $490. It Hasn't Lost Any Of Its 1920s Charm.

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