How Classic Hamptons Hotels Stay Some of the Best

With new hotels and restaurants opening and closing on the East End year after year, these classics have not only stood time’s test, but have made updates and renovations to stand up against even the shiniest newbies.  Here is a look at what some of the oldest hotels in the Hamptons are doing to continue to stay some of the best.

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Harbor Hall

Ram’s Head Inn, Shelter Island, NY

Ram’s Head Inn

108 Ram Island Drive

Shelter Island, 11965

The Ram’s Head Inn on Shelter Island reopened this spring after closing for repairs and updates during the winter months.  The classic waterfront hotel and restaurant, built in 1929, unveiled a $20,000 renovation which included a new sound system, updated decor and lighting, and a new look to their popular bar & lounge, newly dubbed “Harbor Hall,” which included tables personally hand- crafted by owner James Eklund.  Several guest rooms were renovated and redecorated as well.  James and wife Linda Eklund have been at the helm since 1979 and have taken care to keep this beauty in pristine condition. Guests get the full experience of a chic and relaxed Shelter Island vacation at the airy inn, its award winning farm-to-table restaurant, and its expansive beachfront grounds offering amenities like tennis and bocce.  The Inn most recently partnered with Elements Fitness bringing Beachfront Barre and paddleboard lessons, rentals, and excursions to the waterfront property.


Gurney's Montauk

Gurney’s Montauk, Montauk, NY

Gurney’s Montauk

290 Old Montauk Hwy.

Montauk, 11954


Since new owners took over in 2013, the 90-year-old oceanfront resort has been undergoing a major facelift which now boasts 42 newly renovated rooms, a 30,000 square-foot spa and sand-filtered seawater pool, and new dining options.  The interiors now do justice to the unbeatable views and location

Southampton Inn


Southampton Inn, Southampton, NY

Southampton Inn

Southampton, 11968


Combining casual Hamptons style with European comfort, the Southampton Inn has been a local landmark for three generations. The most recent update to this classic boutique hotel is the addition of Café Klyde, a farm-to-table restaurant. Guests will experience well priced, locally sourced options, with plenty of selections for vegetarian, vegan, and gluten free diners – all within a family friendly environment. Guests have a choice of dining outside in the Inn’s courtyard or in the renovated 68-seat dining room. Carry Out is also available for guests to bring to the pool patio, the beach, or on a bicycle excursion.


Topping Rose House

Topping Rose House, Bridgehampton, NY

Topping Rose House

1 Bridgehampton – Sag Harbor Turnpike

Bridgehampton, 11932


The 22-room, 1890’s-era inn is celebrated chef Tom Colicchio’s first foray as a hotelier, and food is a major part of the experience by Kyle Koenig, a Colicchio protégé. The main house rooms retain the original charm and feel of the Greek Revival-style mansion, yet offer modern amenities such as flat-screen TVs, iPod docks, and free Wi-Fi.


C/O Maidstone, East Hampton, NY

C/O – The Maidstone

207 Main St, East Hampton, NY 11937


The Maidstone has maintained its residence since 1740, yet this classic Hamptons institution has a modern and eclectic feel due to owner and hotelier Jenny Ljundberg who took over the property in 2008.  Ljungberg is responsible for its unique and modern Scandinavian decor, and updated onsite restaurant as well as modern amenities such as onsite yoga classes provided by popular East Hampton studio Elements Fitness. The chic, eclectic guestrooms feature different themes, ranging from old-world regality to contemporary Finnish design. All have private bathrooms, WiFi, TVs, DVD players, and minibars. There are also 3 Swedish-style cottages.

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