One Of America's Best All-Inclusive Resorts Is A Rustic Gem In Rural Vermont With Year-Round Charm

Laureled in the Oprah Daily Hotel O-Wards as one of the best couple's hotels of 2024, Twin Farms is a five-star, 300-acre, all-inclusive resort about 10 miles north of Woodstock, America's most beautiful town. Step through the gate into Twin Farms and it won't take long to understand why this resort has received so many accolades, as the embracing hills and dales encapsulate Vermont, as if pulled directly from paintings by American folk artist, Grandma Moses. Among meadows, forests, ponds, gardens, and even private ski slopes, Twin Farms places its 10 freestanding cottages, eight treehouses, four farmhouse suites, and private lodge, each with their own flavor and personality reflected in names like aviary, chalet, orchard, and perch.

At the heart of the estate is the farm itself. Originally built in 1795, it earned enormous pedigree in the 1920s when it was purchased by Nobel Prize–winning author Sinclair Lewis for his wife, journalist Dorothy Thompson. The couple spent time here writing and entertaining, throwing parties that often welcomed celebrities of the day. The property was later sold in 1958 and passed through several owners until a wealthy businessman and philanthropist from Hawaii transformed it into a hotel in the 1980s. In 1993, under new owners, it opened as Twin Farms. Since then, the five-star resort has racked up enough awards to fill a trophy case, including two-key status by the Michelin Guide, hotel of the year by Forbes, and number one resort in the Northeast by Condé Nast.

Each accommodation at Twin Farms is a world unto itself, making it possible to stay many times and have a different experience. The Barn cottage, for example, presents traditional Scandinavian-style architecture with exposed beams arching to a high ceiling above a bi-level stone fireplace. The Log Cabin lives up to its name with hand-chopped hickory and oak beam walls, rustic cabinetry, and an enclosed porch — all surrounded by a pine forest. The Meadow cottage channels Moroccan influences with tented ceilings, terracotta floors, and moucharaby window screens. The most popular cottage, however, remains Woods, which transports guests to Tuscany with elements like a 19th-century Italian oak writing table and a hand-thrown brick fireplace.

In 2023, Twin Farms expanded its offerings with eight new tree houses. Hovering 14 to 20 feet above the ground and reachable only by bridge, these units create the impression of floating among the trees — a sensation only enhanced by the Japanese concept of wabi-sabi, which centers on the impermanent-nature and beauty of earthly things. This is manifested in elements like the organically-shaped furniture and beds placed near windows so that guests can gaze out at the surrounding trees and wildlife. Those fascinated by Twin Farms' literary history can stay in main house, including in Sinclair Lewis' own bedroom. Some of the main house units are only steps from the dining room, a plus for those with mobility issues. 

Perhaps the best signal of the top-shelf luxury offered at Twin Farms is the art collection. Hanging from the walls are works by David Hockney, Cy Twombly, and Jasper Johns. But that's just the proverbial tip of the iceberg. This luxury extends to the dining, too. Produce, meat, and dairy at the resort are sourced from nearby farms, while maple syrup and honey come from Twin Farms' own trees and hives. Furthermore, all meals can be paired with a lovely wine from the resort's 16,000-bottle collection. 

In addition to the gorgeous accommodation and great dining, there is a spa that offers massages, facials, lifts, and other treatments. You can even follow your spa visit up with a dip in the 104-degree-Fahrenheit salt water of the Japanese onsen or head outside for archery, kayaking, hiking, swimming, and tennis. In winter, guests can spend the day skiing on the resort's six private slopes, fishing, iceskating, and snowshoeing. Of course, all of this luxury comes at a price — one night here can run you roughly between $3,000 and $4,000, and there's a three-night minimum. However, Twin Farms has a certain year-round rustic charm that makes the stay worth it. This resort also makes a great home base for further Vermont experiences, including one of the East Coast's most scenic ski resorts where you can also step onto America's oldest long-distance hiking trail.