If a 1970s surf lodge and a high-end coastal resort had a baby, it would be The Wanderer Cottages in Kennebunk, Maine. Nestled on Sea Road, The Wanderer features 17 clapboard cottages and one three-bedroom house.
Each cottage’s design draws inspiration from its prime location in one of Maine’s top surfing towns, with vintage surf photos, gear, and books adorning every corner. The amenities channel the spirit of a luxury beach resort, offering complimentary s’mores kits, Grown Alchemist bath products, a fleet of basketed bikes, and fresh breakfast delivered to your doorstep every morning at 8 AM.
Set in the charming coastal town of Kennebunk, The Wanderer Cottages make for a perfect escape from Boston in every season—summer for the beach, fall for the foliage, and winter for the holiday prelude in what’s known as “America’s second-best Christmas town.”
Wander more
Adventure lies at the heart of The Wanderer Cottages. Staying in one of the cottages feels like an artist’s retreat—an author or painter escaping the city hustle, inspired to explore the natural beauty of southern Maine. The cruisers offer a scenic route to reach the beach or downtown, both just a 15-minute bike ride away. Complimentary beach chairs and towels mean you can leave the headache of beach gear at home.
On the property, a refreshing dip is just steps from your door. The centerpiece of the lawn is a five-foot-deep, 84° heated outdoor saltwater pool open 12 hours a day. On Tuesday and Thursday mornings, unwind with yoga on the lawn led by Jennifer Gallo—a Mainer with over a decade of yoga instruction experience.
Cap a day of exploration with a bonfire and s’mores under a starry sky in your new backyard. After a day outdoors, relax in cottage comforts with aromatic Grown Alchemist products, an in-room Keurig stocked with coffee, tea, and hot cocoa, inspiring reads on surf culture (or a massive TV if you prefer), and soothing indigo decor that evokes a luxe surfer’s retreat.
Things to do in Kennebunk
Centrally located, The Wanderer Cottages are just a stone’s throw from Maine’s pristine beaches, nature trails, endless antique shops, and delicious restaurants—whether you’re craving a lobster roll or a prix fixe meal.
The Wanderer is a quick drive or bike ride to Kennebunk Beach, which features a children’s playground; Gooch’s Beach, a popular surf spot; and Goose Rocks Beach, a wide stretch of sand with island views. Rachel Carson’s Wildlife Refuge offers a gorgeous setting to take in ocean and foliage views along a one-mile trail. For a longer loop, explore the Eastern Trail—over six miles of flat, easy, and scenic terrain connecting Kennebunk with Biddeford and Arundel.
For a scenic oceanfront route in town, take Ocean Avenue or Marginal Way in Ogunquit. Local restaurants like Barnacle Billy’s, Earth at Hidden Pond, and Rosella serve incredible coastal fare. For a sweet treat, the blueberry pie ice cream from Big Daddy’s is pure perfection.
Kennebunk neighbors Wells, Ogunquit, and York—all connected by U.S. Route 1, which doubles as both a scenic drive and an antique trail, lined with shops offering everything from vintage oars to rare seaside treasures. For a truly Maine experience, hop on a scenic cruise or whale-watching tour, or join a private oyster shucking class with Lady Shuckers.
A coastal getaway for any season
While summer is undeniably a delightful time to visit these surf-inspired cottages near several Maine beaches, the shoulder season—and even winter—offer equally charming reasons to plan a trip. Snagging a bottle of The Wanderer’s homemade blueberry simple syrup is reason enough to crave a visit year-round.
Surf season in Kennebunk begins in spring and remains popular through fall, so you can catch a lesson with Aquaholics and ride the waves at Gooch’s Beach even during the shoulder season. Guests booking shoulder season stays also enjoy a 20% discount on visits of three nights or more. The cottages are open through October 26, 2025, and reopen on May 7, 2026—so there’s still time for one last weekend getaway!
Come winter, The Wanderer Cottages invite guests to call “On The Rocks,” the property’s three-bedroom house a home during Kennebunkport’s annual Christmas Prelude.
The tiny Maine village transforms into a scene straight out of a Hallmark movie, with festive activities happening daily—earning it the title of “America’s second-best Christmas town.” You can live out your winter fantasy with a stay at the home for any three or more nights between December 4–14, with bookings confirmed by November 28.
Learn more and reserve your stay!