The Oaks Waterfront Hotel Review: Eastern Shore Luxury | Better Living

Searching for your next Chesapeake Bay getaway? My Oaks Waterfront Hotel review covers three days at this intimate property in Easton, MD that surprised us with impeccable service and genuine Eastern Shore charm.

The Oaks Waterfront Hotel Review – Easton, MD

Tucked away on a quiet cove just off the Chesapeake Bay, The Oaks Waterfront Hotel delivers a serene escape that feels like your own private corner of Maryland’s Eastern Shore.

After spending three days here, I can confidently say this boutique property surprised us in the best possible way.

What caught me off guard was how much it reminded me of some of the world’s finest hotels. The Oaks may be a boutique property rather than a sprawling resort, but the level of service and attention to detail rivaled what I’ve experienced at places like Four Seasons or Ritz Carlton.

Fresh flowers appear throughout the property each day. The restaurant and bar are always set up to look picture perfect. The lobby welcomes you with coffee, tea, and snacks that make it inviting from the moment you arrive. Everywhere you look, the property appears pristine and almost brand new. Premium amenities fill the rooms – quality furnishings, linens, and robes that add extra comfort. Getting around is effortless with golf cart rides across the grounds or a luxury SUV on call for shopping and dining. Their own yacht waits at the pier. Fine dining and signature cocktails happen on site, all delivered with service that feels like having your own personal concierge.

Like those big-name properties, everything is simply taken care of and waiting for you on arrival. It’s all very thoughtful and luxurious. The difference is that The Oaks delivers it all with genuine warmth instead of polished formality.

What Makes The Oaks Special

The Oaks sits on 10 acres of waterfront property with a fascinating history dating back to a 1680 land grant from Lord Baltimore. The main building, a colonial revival structure from 1902, underwent a $10 million renovation that shows in every corner, yet it never seems overdone. Its recent inclusion in Historic Hotels of America reflects both its historical significance and commitment to preservation.

The property offers 11 rooms and suites in the main building, plus four waterfront cottages for ultimate privacy. We stayed in Cottage 3, and it quickly became clear why these accommodations are in such high demand.

The Oak Room offers elevated cuisine with water views, and the breakfast alone makes it worth starting your day at the hotel.

The property also offers curated experiences – including water sports, yacht charters, clay shooting, and golf, that immerse you in the Chesapeake Bay lifestyle.

What stood out most was the staff. They knew our names right away and were sharing stories about the property’s centuries-long history by the time we had settled in. The same team that checked us in later helped with our meals, arranged restaurant outings in St. Michaels, and drove us from the parking area to our cottage with our bags in a golf cart. Their attentiveness and genuine warmth made us feel truly welcomed.

Our Stay in Cottage 3 at The Oaks

Cottage 3 living room with water views at The Oaks | Photo: Better Living

We stayed in Cottage 3, and the layout is just right. It’s spacious, bright, and comfortable, with two TVs and a covered porch where you can watch the water roll by on Oak Creek. Even on a rainy afternoon, the porch became the coziest spot to just sit and enjoy the peaceful views.

The bathroom deserves its own mention. Heated floors feel incredible under bare feet, the walk-in shower is spacious, and the soaking tub is truly deep enough to relax in. The toilet has its own separate room, so two people can use the space without awkward encounters. The robes and towels were wonderfully plush, adding an extra touch of comfort.

The king bed provided some of the most restful nights of sleep we’ve had anywhere. With high-quality linens and pillows, temperature control, and complete quiet, it created ideal conditions for deep rest.

The dining area seats four comfortably and includes a sink, coffee station, and full-size fridge with freezer. This was convenient for storing leftovers from all the fantastic restaurants we discovered. A special tip: the rooms are stocked with some of the best chocolate chip cookies you’ll ever taste. They’re baked onsite, and the staff are happy to bring more on request.

The saltwater pool, located just off the main house, provides a refreshing option during summer visits. It’s perfectly positioned for a quick dip when you want a break from all that relaxation.

What we loved most was the outdoor waterfront seating. Whether enjoying morning coffee or evening wine, the views of the water, pier, grounds, and fire pit create an ideal setting for doing absolutely nothing at all.

Dining at The Oaks

Corn and White Truffle Agnolotti with Lobster at The Oak Room | Photo: Better Living

The Oaks delivers a dining experience that rivals much larger hotels, anchored by Chef Dave’s creative cuisine in The Oak Room and an exceptional breakfast program that sets the tone for each day. With Sujoy’s cocktail artistry behind the bar and service that anticipates every need, meals here become memorable experiences. The Tuesday through Thursday dinner schedule creates an intimate atmosphere, while the complimentary breakfast showcases local ingredients with waterfront views that make early mornings worthwhile. For those arriving by boat, the property’s private pier offers convenient dock and dine access to The Oak Room.

Complimentary Breakfast at The Oaks

Breakfast is served from 8:30 to 9:30 AM in the Oak Room with sweeping waterfront views. This is not your typical hotel breakfast. It’s something worth planning your morning around.

During our stay, we tried nearly everything. The Eastern Shore Omelette with jumbo lump crab, white cheddar, roasted tomatoes, spinach, and skillet potatoes highlights the best local ingredients. The Granola Bowl with Greek yogurt, fresh berries, and house-made granola was lighter but just as satisfying. The Breakfast Sandwich, served on a toasted soft pretzel with scrambled eggs, Red Dragon cheddar, caramelized onions, and your choice of meat, is creative comfort food. It even comes in a takeout container if you’re on the go.

For something a little more sophisticated, the Poached Egg and Smoked Salmon over rösti potatoes with avocado was a standout. The French Toast made with brioche, Chantilly cream, and berries felt indulgent without being heavy.

Service was outstanding. Our water was always topped off and our coffee cups were never empty and always hot. A tip is to arrive early to grab a seat with water views or enjoy breakfast on the covered porch when the weather allows.

Starting each day with views of the water, food this good, and hospitality this thoughtful set the perfect tone for three days of complete relaxation.

Dinner at The Oak Room

The Oak Room is open for dinner Tuesday through Thursday from 4:00 PM to 9:00 PM, and dining here became one of our trip’s highlights. The space is elegant yet welcoming, with dramatic sunset views of Oak Creek and a mix of couples enjoying everything from lively conversations to quiet, intimate meals. Mellow background music stays low enough for conversation, and the service here is impeccable.

We chose booth seating in the bar area for front-row views of the action behind the bar. Chef Dave prepared a special tasting menu and came out to explain each dish, making the experience more personal and engaging.

The Caramelized Watermelon Salad with arugula, pistachio, watermelon radish, and lime and agave vinaigrette was an unexpected delight – sweet watermelon playing against peppery arugula and crunchy pistachios. The Tuna Tartare with avocado mousse, cucumber, sesame seeds, lime, caviar, and tamari was great for sharing. The Corn and White Truffle Agnolotti featured a huge piece of lobster claw with butter-poached lobster and crisp prosciutto – pure indulgence done right.

The Maple Leaf Farms Duck Breast came expertly cooked with sweet potato purée, royal trumpet mushroom, pickled blackberry, and port wine jus. From the regular menu, the Bolognese with Marble Head Farms ground beef, pancetta, linguini, parmesan, and grilled baguette proved that comfort food can be elevated without losing its soul.

For dessert, the Strawberry Crisp won us over with fresh, light flavors, though the Spiced Bread Pudding with vanilla anglaise, fig gastrique, and caramelized peach was equally impressive.

The Bar at The Oak Room: Sujoy’s Cocktail Artistry

Bartender Sujoy transformed our evening into cocktail theater. Each drink was prepared as a carefully crafted performance right in front of us at the bar. The Chocolate Espresso Martini featured freshly grated chocolate falling onto the rim, rich and smooth. The Lemon Drop hit that ideal sweet-tart combination, while the Spicy Margarita built heat slowly without overwhelming your palate. Each drink also paired well with Chef Dave’s plates.

What made the experience even more memorable was learning that Sujoy drives the luxury SUV during the day and tends bar at night, embodying the kind of multi-role flexibility that makes The Oaks work so well. He guided us through each cocktail, explaining techniques and genuinely caring about our experience.

The bar area strikes that elegant-yet-casual balance, with booth, high-top, and bar seating options. Even the coasters bear “1902,” connecting to the property’s founding year. We ended up lingering longer than planned, drawn into the relaxed atmosphere and conversations with other guests.

Sujoy’s attention to detail and personality transformed what could have been just drinks into an interactive experience that made our dinner memorable. We’re already looking forward to seeing what new cocktails he creates on our next visit.

Exploring St. Michaels and Easton: Dining Beyond The Oaks

The Oaks is well positioned between two of Maryland’s most charming Eastern Shore towns, each with its own personality and flavor. St. Michaels is quaint and walkable, with picturesque streets and historic charm. Easton has a slightly larger downtown full of coffee shops, parks, boutique shopping, and great spots for lunch.

Dinner at Bistro St. Michaels

Since The Oak Room was closed on our first night, Bistro St. Michaels was the natural choice, just five minutes away. The restaurant is like part of the town itself, warm and welcoming without being formal. Owned by Chef Doug Stewart and General Manager Jennifer Stevens, it embodies everything we love about Eastern Shore dining.

Chef Doug’s cooking lets flavors develop naturally, resulting in dishes that are delicious and satisfying. The Shrimp & Grits appetizer with stone-ground grits, andouille sausage, marinated prawns, and an aromatic shellfish broth was comforting and vibrant. Fried Green Tomatoes with crab meat, tomato lemon remoulade, and a touch of chile balanced crisp and fresh flavors beautifully.

The famous Braised Beef Short Rib with caramelized Savoy cabbage, onion pommes purée, glazed carrot, thyme bordelaise, and bacon lardon felt like a masterclass in technique, while the Tilefish with Red Quinoa and broccolini let fresh, simple ingredients shine. Dessert was the signature Bread Pudding A La Mode with vanilla gelato and house-made butterscotch sauce, rich and satisfying without being heavy. Service was fantastic and the space, with its granite bar and open kitchen, felt inviting and comfortable.

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Lunch at Tiger Lily Easton

Easton offers a great selection of shopping, parks, and casual dining. Tiger Lily caught our attention for its bold flavors and playful menu. Visiting on Taco Tuesday for lunch, we quickly understood why locals love it.

The Al Pastor Tacos with adobo-marinated pork and grilled pineapple were smoky, sweet, and addictive. Carne Asada Tacos delivered bright, lively flavors, while Birria Tacos highlighted precision in traditional technique. The After School Tacos with taco-seasoned ground beef, cheddar, lime-dressed cabbage, pico de gallo, and crema were unexpectedly satisfying. A Trio of Dips with house-fried tortilla chips, guacamole, salsa, and queso set the tone for the meal. The casual, lively space, 80’s music, and inventive menu made each dish fun and memorable.

Between Bistro’s refined Eastern Shore cuisine and Tiger Lily’s inventive fusion, these two towns provide a variety of culinary adventures that pair beautifully with a stay at The Oaks.

Birding at The Oaks

The Oaks provides an excellent base for birdwatching, with the front desk providing binoculars and Eastern Shore bird guide books to guests. From our cottage and throughout the property, we spotted herons, hawks, ospreys, blue jays, Carolina wrens, and even a pair of bald eagles. We loved being surrounded by the sounds and sights of abundant nature, making every moment outdoors feel connected to the Chesapeake Bay’s natural beauty.

Evening Magic and Meeting Fellow Travelers

As an intimate boutique hotel with just 15 accommodations total, The Oaks creates natural opportunities to meet other guests. We had wonderful conversations with both fellow travelers and staff throughout our stay. The firepit area becomes particularly magical in the evening, with Adirondack chairs arranged around the flames and the water providing a peaceful backdrop for relaxed conversations under the stars.

The property does host many weddings, so weekends can be challenging to book. But this creates an opportunity – midweek stays often offer better rates and a more relaxed atmosphere well-suited for couples seeking a quiet getaway.

When Weather Changes Plans

We had planned to take advantage of the complimentary kayaks and paddleboards, and were scheduled for a sunset cruise on their beautiful 40-foot Hinckley yacht, Overcomer. Rain and wind had other ideas, but rather than being disappointed, it just gave us another reason to plan our return visit. The Oaks is the type of place where weather can’t diminish the experience. There’s always something wonderful happening indoors.

Small Details, Big Impact

Sometimes the smallest touches leave the biggest impression. Those incredible chocolate chip cookies and coffee in our cottage became a daily highlight. The super plush robes made lazy mornings even more indulgent. The heated bathroom floors turned every shower into a spa experience. These details, individually small, combined to create an atmosphere of comfort and ease that elevated our stay.

Planning Your Visit

The Oaks shines year-round, but spring through fall offers optimal weather for outdoor activities and yacht excursions. The waterfront cottages provide maximum privacy and stunning views – book well in advance, especially for weekends and peak seasons.

Three days allowed us to experience The Oaks thoroughly while exploring both St. Michaels and Easton without feeling rushed. Two nights works for a romantic getaway, but you’ll likely find yourself wishing for more time.

Why Choose The Oaks for Your Eastern Shore Getaway

The Oaks delivers something unexpected – a boutique property where you can simply relax in luxury and let the staff pamper you. It’s perfect for a quick getaway where every detail is handled and you don’t have to think about anything except enjoying yourself.

The peace and relaxation we found here, combined with culinary artistry, creates the type of getaway that stays with you long after checkout.

The worst part of our stay was leaving, but we’re already excited to return when the seasons and menus change. Bring your appetite and prepare to be surprised by what you’ll discover tucked away on Maryland’s Eastern Shore.

Directions To The Oaks