Five Motor-Inns and Motel-Inspired Spots for a Retro Road Trip from Boston (2024)

Voyaging vintage-style to the Berkshires, Saratoga Springs, and more.

Ah, the family road trip. Remember piling into the car with some snacks, breezing down the highway, and rolling into a no-frills motel to get some shuteye? If you could use a little break from the present, nostalgia for a simpler time abounds at these five area motels and motor-inn inspired lodgings, each with a retro dose of welcomed kitsch. And in the time of COVID, these spots might just offer a safer way to travel—with much fewer rooms, and the ability to avoid common areas like long hallways and elevators.

The Briarcliff Motel
Great Barrington, MA

The Briarcliff Motel paints an alternate past where the 1960s boasted free wi-fi. Park right outside the strawberry-red door of your room, where you’ll lounge in retro-steeped surroundings, from the pattern-play of polka dot and florals, to the streamlined furniture and vintage tiles and fixtures in the bathrooms. The staff infuses the motel with a B&B heartbeat, with fresh-baked scones in the mornings and joe from nearby Barrington Coffee Roasters. Monument Mountain lies just across the street, so after a day of exploring, the cozy outdoor fire pit beckons for some unplugged quality time.

506 Stockbridge Road, Great Barrington, MA, 413-528-3000, thebriarcliffmotel.com.

Tourists
North Adams, MA

You can spot Tourists’ past as a single-story motel complex, with its white-oak-sided buildings tucked into 30 acres of native wetlands, meadows, and forest clearings. Here, the design leans into nostalgia: pillows with vintage textures, weathered wood, and family heirloom-looking leather couches in the lodge. Rear doors, mirroring the front doors of each of the 48 guest rooms, lead to back decks where guests can bathe al fresco in the outdoor showers. Elsewhere, a 220-foot suspension bridge beckons to a network of lush trails. Not that you need to travel far to let nature into your room. “By design, the rooms replace themselves completely with fresh outdoor air on average every hour,” says owner and lead partner Ben Svenson. “With the pandemic, this feature has proved more important to guests than we ever anticipated.”

915 State Road, North Adams, MA, 413-347-4995, touristswelcome.com.

The Jack Daniels Motor Inn
Peterborough, NH

You wouldn’t be the first to mistake the Jack Daniels Motor Inn in Peterborough, New Hampshire as a hospitality offshoot of the Jack Daniel’s whiskey brand, but what a difference an apostrophe makes. A motel has existed here since 1948, tucked by the Contoocook River, and in 1975, Frances and Daniel O’Rourke and Jean and Jack Bullock bought and overhauled the property. “Named for Jack Bullock and Dan O’Rourke, the inn has kept the Jack Daniels Motor Inn brand even after the Bullocks and O’Rourkes sold the property in 1996,” says owner Eric Lorimer. This no-frills cozy spot in the Monadnock region of southern New Hampshire is both a quick stroll to downtown Peterborough and the serene solitude of the river. That’s something we can say “cheers” to.

80 Concord St., Peterborough, NH, 603-924-7548, jackdanielsinn.com.

The Cove Motel
Orleans, MA

The Cove Motel boasts the best of the Cape—those sweeping waterfront views, the heavenly breezes—while at the same time letting you avoid the crowds and save a decent chunk of change on lodgings. What the 47-room spot, built around 1959, lacks in suites and spas, it more than makes up with flashbacks to family vacations of yesteryear. Here, it’s less frills, more grills. Plus, picnic tables, sun-soaked decks, and a gleaming public pool (remember those?). Outdoor games like shuffleboard and cornhole invite you to stash your phone and play, or at least lounge by the fire pit. Plus, you can easily hop the Cop Cod Rail Trail and bike all the way to Provincetown, or hoof it to the nearby shops of Orleans.

13 South Orleans Road, Orleans, MA, 508-255-1203, thecoveorleans.com.

The Downtowner
Saratoga Springs, NY

The Downtowner’s former life as a 1960s motel sings through the design details of these boutique lodgings, which opened in 2018, just steps from the racetracks and restaurants of Saratoga Springs. “The building is a mid-century gem, and we preserved its bones as much as possible when renovating and redesigning the property,” says Rich Cooper, partner at Bluefish Hospitality Development, which worked with Amesbury-based Lark Hotels on the project. You’ll find nods to mod in the 42 guest rooms, from the sleek furniture to the artwork and the design duet of wood and concrete. But the best throwback? The sun-soaked, lofted atrium, where a blue rectangle of polished concrete sits in place of a former pool, making for the perfect lounge to enjoy some co*cktails.

413 Broadway, Saratoga Springs, NY, 518-306-4063, thedowntownerhotel.com.