Five Gorgeous Historic New England Homes You Can Vacation In

Photo by Irvin Serrano

If there’s one thing New England is known for, it’s tiny towns full of character. But with big box hotels popping up on what feels like every corner, it’s time to take a moment and appreciate the special historic properties in the region that have been turned into boutique hotels, like the farmhouse where Sinclair Lewis proposed to Dorothy Thompson, and the seaside enclave that once hosted Amelia Earhart. Because sometimes you want to staycation like a rock star, but other times you just want to imagine what going to bed like a wealthy sea merchant from the 19th century feels like. 

The Francis

Tucked in Portland’s West End, The Francis is named for its architect, Francis Fassett. Though he designed the hotel for Portland merchant Mellen E. Bolster in 1881, Fassett left his mark all over the West End of Portland, particularly after the Great Portland Fire of 1866 ravaged the city. He designed the Baxter Library, the original Maine General Hospital Building (which later became Maine Medical Center), the Second Parish Church, and the former City Hall building. The Francis later became a funeral home, before falling into disrepair for many years. New owners bought it in 2015, and after a two-year renovation, it’s now a 15-room hotel and spa with a 49-seat restaurant. But the property still manages to showcase many of its historic details, like the original wood flooring, as well as beautifully restored stained glass windows on the front doors.

747 Congress St., Portland, Maine, thefrancismaine.com. 

Courtesy photo

Hotel Marblehead

Not many homes can count Amelia Earhart as a guest, but the Hotel Marblehead can. Tucked in the seaside enclave about 16 miles north of Boston, the Hotel Marblehead was originally a stunning Victorian home built in 1872 by Marblehead resident J.P. Harris. Harris died before the home was completed, and the property was passed through several owners, including a prominent shoebox manufacturer, a local leather merchant, and a lawyer over the next two decades. It became a guest house in the 1920s, which is the period when Earhart stayed there while living in Medford. Though it has since changed ownership a couple times, the property went under significant restoration before reopening in early 2018. Now, it’s a stunning 14-room boutique hotel with a nautical vibe. The Hotel Marblehead has an upcoming star turn too: The property was recently “dressed” for an appearance in the Adam Sandler Netflix film Hubie Halloween.

246 Pleasant St., Marblehead, Massachusetts, TheHotelMarblehead.com. 

Photo provided

Twin Farms

These days it’s one of Vermont’s ritziest escapes, but Twin Farms is steeped in literary history. When author Sinclair Lewis proposed to journalist Dorothy Thompson, she said she would marry him if he bought a sprawling farm in Vermont. Thompson actually managed to get what she wanted, and the couple plunked down $10,000 for a old farmhouse on 300 acres in the bucolic town of Barnard. Some of the greatest political and literary minds in the world came to hang with the couple at Twin Farms, where they threw legendary parties. While the couple eventually split, Twin Farms lives on as an adults-only oasis offering luxe experiences ranging from bee tours with their resident apiarist to a hot soak in the Japanese Furo. With a stunning setting amidst rolling hills and acres of wildflowers, it’s the picture of idyllic New England.

452 Royalton Turnpike, Barnard, Vermont, www.twinfarms.com.

Photo by Read McKendree

The Cliffside Inn

Newport’s history (and current status) as a luxurious playground for the rich is extensive, and that fascinating backstory is on full display at the Cliffside Inn. The Second Empire Victorian Manor House was built as a summer home in 1876 by Maryland Governor Thomas Swann, who named it Swann Villa. It later became a schoolhouse, and even became the first home of the prestigious St. George School. Later, cotton merchant Andrew Turner purchased the home, and his daughter Beatrice remained at Cliffside until her death in 1948. A Newport legend and successional 20th century painter, Beatrice’s artwork still adorns the property. 

2 Seaview Ave., Newport, Rhode Island, thecliffsideinn.com.

Photo courtesy of the Kennebunkport Resort Collection

Kennebunkport Inn

Kennebunkport is steeped in maritime history, and the inn that bears the town’s name is a prime example. At the dawn of the 19th century, the Perkins, a family of wealthy sea captains and merchants, took hold of 15 acres in front of the Kennebunk River, and built their family home there. The estate was passed down to seven generations of the family, until it was finally sold in 1888. The original property was torn down by Burleigh Thompson, who built his own sprawling home, which was known as “one of the most desirable estates in Kennebunkport … the house [having] been built without regard to expense.” The exquisite Federal-style home had everything from 400 feet of water frontage to a horse stable. Through the 1900s, the estate was bought and sold a couple more times, and eventually became an inn. Now, there’s 35 rooms in the main inn and adjacent Riverhouse building. 

One Dock Square, Kennebunkport, Maine, kennebunkportinn.com.