Close, drivable weekend getaways have become even more important to many Americans. This close trip is not seen as a compromise, but rather as a more convenient, relaxing getaway without the hassle of airfare and long travel times.
Hilton’s 2026 Trends Report revealed that more travelers are choosing journeys that involve ground travel and “keep them connected to the landscape” and nature. This year, a third of summer travelers are opting to stay closer to home, and “short-haul playcations” are driving US summer travel trends, with people looking for destinations with active hobby options, including boating and golfing, according to Airbnb’s 2026 Summer Travel Trends.
Similarly, IPX1031’s 2026 travel survey found that “nearly a third (32%) of Americans have changed destinations due to flight prices, while 27% have decided not to travel at all because of airline fees like baggage and seat selection costs.”
The Oaks Waterfront Hotel in Easton, Maryland, is a prime example of this ideal getaway, with its natural beauty, elevated amenities and accommodations, and location an easy 90-minute drive from Washington, D.C. and Baltimore, Maryland.
You can experience the relaxation of a true vacation at The Oaks, without a long travel day or airport chaos. At this spot, you are immediately immersed in the Eastern Shore’s easygoing atmosphere that is the polar opposite of the bustle of its neighboring cities.
A Warm Welcome That Sets the Tone
As soon as you arrive at The Oaks, you are warmly welcomed in the lobby and given a brief tour of its historic property that dates back to the 17th century. The Oaks was inducted into Historic Hotels of America® in 2025 and was recognized as one of the Top 25 Historic Hotels of America® for a Romantic Proposal in 2026.
The Oaks property is cozy and compact in size, which makes it easy to enjoy all its amenities and offers a home-away-from-home feel during your visit.
Linda Warner, guest services specialist at The Oaks, is one of the warm and welcoming staff members you’ll meet during your stay. Linda described this property as a “place where relaxation comes naturally” with its “thoughtfully designed décor and beautifully manicured grounds [that] have been carefully curated to create an atmosphere of comfort, tranquility, and luxury.”
Linda explained that it’s their culture that sets The Oaks apart, noting, “our entire staff believes exceptional hospitality is about more than providing a beautiful place to stay—it’s about anticipating needs and making every guest feel genuinely cared for.” Linda further shared, “When we say, ‘Welcome to The Oaks,’ it means you will be welcomed like family, cared for with intention, and treated with warmth.”
This genuine hospitality is echoed throughout the property’s accommodations, waterfront Adirondack chairs, saltwater pool, cozy firepit, and Oak Room restaurant. Parking is also generous (complete with electric vehicle chargers).
Accommodations Designed for Recharging
In all of The Oaks’ accommodations, you will notice elevated, thoughtful touches throughout. You can enjoy plush beds, luxury bathrooms with deep soaking tubs and heated floors, and complimentary breakfast at the Oak Room.
You will also find individual climate control, complimentary Wi-Fi, TVs with Apple TV, robes, a clothing steamer, a hairdryer, and a coffee maker. Your mini fridge is also stocked with complimentary water and a variety of sodas.
In The Oaks’ main building, you can choose between their eight well-appointed rooms or three suites, with options including water views, private balconies, and/or soaking tubs. You can also enjoy one of their four spacious cottages, each featuring a king bed, kitchenette, large bathroom, and private patio with water views.
A cottage stay is spacious, with a generous living room, kitchenette, bedroom, and large bathroom, including a walk-in shower and a deep soaking tub. A bath is especially dreamy, with the tub set next to a large window that floods the bathroom with sunlight and views of green trees.
The Oak Room Is a Destination in Itself
One of the best parts about staying at The Oaks is their restaurant, The Oak Room. Guests can enjoy a complimentary à la carte breakfast each morning, and can have dinner Sunday through Friday.
On Sunday and Monday, dinner service is available exclusively for hotel guests with a limited menu, while on Tuesday to Thursday, dinner is open to the public for happy hour and dinner this summer.
With its curated, fresh menu, this spot is a dining destination for those in the area. Their halibut with fingerling potatoes, asparagus, and saffron beurre blanc is a standout dish alongside their duck breast with sweet potato hash, duck confit, arugula, and duck fat vinaigrette.
Make sure to save room for dessert too; the seasonal fresh fruit cobbler with ice cream is too good to miss. Dinner reservations are recommended.
Their breakfast includes a wide variety of dishes, including their breakfast sandwich with scrambled eggs, red dragon cheddar, caramelized onions, and sausage or bacon, served on a toasted soft pretzel, or their sunrise tostada with a corn tortilla and poached egg with chorizo, black beans, roasted tomatoes, smashed avocado, cotija cheese, and salsa verde.
For those who love something sweet, their French toast with brioche bread, chantilly cream, and fresh berries, or yogurt bowl with fresh berries and house-made granola, are always good options.
Easy Days and Elevated Experiences on Property
On the property grounds, you can enjoy their saltwater pool, complimentary bicycles (including helmets), kayaks, and paddleboards. The waterfront Adirondack chairs are ideal in the morning with a hot cup of coffee and a good book, and are a perfect spot to enjoy golden hour at sunset with a crisp white wine or cocktail.
For a good dose of nostalgia, stop by the front desk for a complimentary s’mores kit (complete with house-made marshmallows) and enjoy The Oaks’ firepit nestled in their waterfront garden. It’s also a perfect spot to read a good book before calling it a night.
If you’re looking for an experience to enhance your getaway, The Oaks offers a variety of waterfront activities and luxury experiences, from clay shooting and boating to exclusive golf tee times and VIP shopping experiences.
For those who especially love a relaxing evening on the water, booking an aperitivo boat ride on the Oak’s 40-foot Hinckley yacht, the Overcomer, is an absolute must. The craftsmanship on this yacht is truly remarkable, creating an elevated experience. Guests and non-guests can book this experience every Tuesday and Thursday (weather permitting).
A Short Drive to St. Michaels and Easton
You can also arrange for The Oaks’ complimentary driver to explore Easton and St. Michaels and enjoy the small-town charm. Both of these quintessential historical Eastern Shore towns are full of cafes, shops, and restaurants, and are conveniently within 15 minutes by car from The Oaks.
Some must-visit spots in St. Michaels are The Galley for lunch, Book Hounds for a good book, and Eat Sprout for specialty coffees, açai bowls, and salads. Gourmet by the Bay is also a perfect spot to pick up fresh breads, wine, and gourmet cheese to bring back to The Oaks and enjoy on your cottage porch or in the waterfront Adirondack chairs.
In downtown Easton, Out of the Fire is an exceptional, inventive kitchen offering creative, beautifully prepared dishes and cocktails, with a commitment to environmental sustainability and to supporting its local community.
The Wardroom is also a great spot for seasonal dishes and wine, with 24 wines available for self-serve via their enomatic system and over 400 wines from their Italian wine list. These two spots are ideal lunch options to enjoy when you spend a day exploring Easton.
The Reset You Have Been Needing
A stay at The Oaks offers a true reset surrounded by nature, only 90 minutes from Washington, D.C., and Baltimore, Maryland. Here you can unwind and recharge without the long travel-day stress and cost, and have the actual getaway you’ve been needing. The Oaks offers that relaxation from the start.
Katherine Woodward Ramer is a freelance digital creator and travel writer with a background in strategic communications, public health, and policy. She spent over ten years in the government and nonprofit sectors, where she specialized in making complex topics clear and engaging.
Now, she creates content for Wander Worthy, a travel publication focused on curiosity, connection, and mindful exploration. Her work highlights travel as a tool for personal growth, cultural understanding, and balanced living through compelling visual storytelling.
