The Northeast has no shortage of great hotels. From meticulously restored Gilded Age-era mansions to sophisticated, modern city hotels. For guests who are looking for a more unique experience, the Northeast certainly isn’t lacking when it comes to luxury accommodations with a bit of an edge.
Offering guests something unique (without being camp) is difficult to do, but the hotels and resorts on this list pull it off with aplomb. Each stay is located near a Tradewind-accessible airport, making a quick weekend getaway as stress-free as it is fun with a private charter flight.
The Liberty Hotel
Boston, MA
Guests of Boston’s Liberty Hotel might be surprised to learn the building from 1851 is the home of a former jail. Nestled in Boston’s Beacon Hill neighborhood, the historic jail hotel cheekily calls back to its history with wrought iron window details and industrial-looking brick walls. The building was designed by architect Gridley James Fox Bryant and prison-reform advocate Rev. Louis Dwight. It is thought to be one of the city’s best examples of the mid-19th century Boston Granite Style.
For more than 120 years, The Liberty Hotel housed some of Boston’s most dangerous criminals before ceasing operations in 1990. What followed was a painstaking renovation that preserved the building’s history, while refurbishing the hotel to a level of luxury that guests expect. The hotel centers around a 90-foot atrium, and its lush private courtyard garden is the former prison yard. History buffs will enjoy learning all about the hotel’s past in the weekly history tour, which takes place on Wednesdays at 2 p.m. (and ends with a glass of Champagne).
Airport: Boston, Boston Logan International Airport (BOS/KBOS)
Hidden Pond
Kennebunkport, ME
Despite being located on the most bustling section of the southern Maine coast, the luxury resort Hidden Pond manages to feel like its own little world. Adult summer camp vibes prevail at this sprawling resort near Goose Rocks Beach. Balsam Fir-lined pathways lead to individual cottages, making each guest feel as though the property is entirely theirs. The treehouse-inspired Treetop Lodges have a Swiss Family Robinson feel—but offer a considerable step up in the luxury department.
The treehouse theme continues at the property’s Tree Spa. Find Three standalone treatment rooms that are elevated off the forest floor and accessible via birch-tree-lined pathways. You’ll hear nothing but the sound of the wind rustling through the trees as you relax and unwind with the 90-minute Tree Spa Signature Treatment.
Airport: Kennebunkport, Biddeford Municipal Airport (B19)
Newport Rose Island Lighthouse
Newport, RI
Newport’s Rose Island Lighthouse offers a rustic experience unlike any other spot in the Northeast. Located on a small island in the middle of the Narragansett Bay between Jamestown and Newport, the historic light station has been converted into a small lighthouse hotel. Guests are ferried to the 18-acre Rose Island and then have full access to the lighthouse grounds.
The island features a number of unique accommodations, including two guestrooms on the first floor of the lighthouse museum, a lighthouse keeper’s apartment, foghorn room, and the Fort Hamilton barracks room, which has housed guests in its historic barracks built in 1798.
Airport: Newport, Newport State Airport (NPT/KUUU)
Winvian Farm
Morris, CT
Located just 30 minutes from Tradewind’s headquarters at Waterbury-Oxford Airport (OXC), Winvian Farm masterfully marries luxury and playfulness to create a truly one-of-a-kind experience for guests staying for leisure or specialized executive team retreats. The Litchfield County Relais & Chateaux resort has received scores of accolades since it opened in 2007, including the AAA Five Diamond Award and several Condé Nast Traveler Readers’ Choice Awards.
At the center of the 113-acre property is the Seth Bird House. Built in 1775, it houses the property’s only non-standalone accommodation, The Hadley Suite. All other guests stay in one of the property’s 18 themed cottages, designed by 15 different architects. Among the most unique are the Treehouse cottage, which suspends 35 feet above the forest floor and offers unparalleled privacy and views of the surrounding forest. The Helicopter cottage, which holds a restored 1968 Sikorsky HH-3F Pelican helicopter that provides a hangout space for aviation buffs. The Library cottage’s double-height living room is lined with bookshelves featuring a collection of treasures and complete with ladders to reach the books on the highest shelves. To those who haven’t visited, Winvian Farm has to be seen to be believed.
Airport: Oxford, Waterbury-Oxford Airport (OXC/KOXC)
Lake Placid Lodge
Lake Placid, NY
Nestled in the heart of the Adirondacks on the shores of Lake Placid sits Lake Placid Lodge, its craftsman-style main building forming the heart of this hidden retreat. The village of Lake Place is in the upper reaches of New York State. It has long been a favorite destination for outdoor recreation (notably for being a two-time Winter Olympics hosting site.) As leisure time increased in the late 19th century, Lake Placid was discovered by wealthy vacationers, who built enormous lodge-style homes known as the Great Camps, and Lake Placid Lodge is modeled in their image.
What makes the lodge unique even among Lake Placid resorts is its decor. Each room, suite, and cabin features its own unique design, many of them furnished by different Adirondacks craftspeople. In the Owl’s Head cabin, the four-poster bed is designed to look as though the posts are tree trunks growing out of the forest floor. While the Treetop and Whiteface rooms feature hand-crafted twig-thatched beds that give the rooms an otherworldly vibe. With most rooms offering sweeping views of Lake Placid and Whiteface Mountain, Lake Placid Lodge is a retreat you won’t want to leave.
Airport: Lake Placid, Lake Placid Airport (LKP/KLKP)
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