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The Oaks Waterfront Hotel Review: Eastern Shore Luxury

by | Sep 29, 2025 | Lifestyle

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

Impressive white colonial revival hotel building featuring multiple gables, black shutters, and covered entry portico supported by columns. The circular driveway is paved with dark asphalt and includes golf cart parking areas. Manicured landscaping with foundation plantings and a brick-edged entrance create an elegant arrival experience. The Oaks main hotel building with arrival area | Photo: Better Living

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.

Bright, elegantly furnished lobby featuring cream-colored sofa and plaid upholstered armchairs arranged around a round glass coffee table. Large windows with neutral Roman shades frame views of green lawn and water beyond. The space includes warm wood floors, neutral area rug, and coastal-themed artwork on pale gray walls.
Bright, elegantly furnished lobby featuring cream-colored sofa and plaid upholstered armchairs arranged around a round glass coffee table. Large windows with neutral Roman shades frame views of green lawn and water beyond. The space includes warm wood floors, neutral area rug, and coastal-themed artwork on pale gray walls. The lobby at coffee station in the main house at The Oaks | Photo: Better Living

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

Expansive green lawn stretching to waterfront with multiple groupings of white Adirondack chairs positioned under beige umbrellas for sun protection. A covered boat slip houses a dark-hulled yacht, while mature trees provide natural backdrop. The peaceful setting emphasizes relaxation and water access amenities.
Expansive green lawn stretching to waterfront with multiple groupings of white Adirondack chairs positioned under beige umbrellas for sun protection. A covered boat slip houses a dark-hulled yacht, while mature trees provide natural backdrop. The peaceful setting emphasizes relaxation and water access amenities. Waterfront grounds with lawn seating and yacht dock | Photo: Better Living

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

Bright, elegantly furnished cottage living room featuring cream-colored sofa and plaid upholstered armchairs arranged around a round glass coffee table. Large windows with neutral Roman shades frame views of green lawn and water beyond. The space includes warm wood floors, neutral area rug, and coastal-themed artwork on pale gray walls.
Bright, elegantly furnished cottage living room featuring cream-colored sofa and plaid upholstered armchairs arranged around a round glass coffee table. Large windows with neutral Roman shades frame views of green lawn and water beyond. The space includes warm wood floors, neutral area rug, and coastal-themed artwork on pale gray walls.
 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.

Serene master bedroom featuring a platform bed with white linens and plaid accent pillow, positioned between large windows overlooking green grounds. The room includes neutral paint, decorative Roman shades with geometric patterns, hardwood floors with area rug, modern chair, and artwork depicting waterbirds. Clean lines and natural light create a peaceful retreat atmosphere.
Serene master bedroom featuring a platform bed with white linens and plaid accent pillow, positioned between large windows overlooking green grounds. The room includes neutral paint, decorative Roman shades with geometric patterns, hardwood floors with area rug, modern chair, and artwork depicting waterbirds. Clean lines and natural light create a peaceful retreat atmosphere. Cottage 3 bedroom with woodland views and luxury amenities | Photo: Better Living

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.

Intimate dining space with round gray wooden table surrounded by upholstered chairs, illuminated by a large nautical-style pendant light with brass accents. A prominent landscape painting depicting marshland and waterways dominates one wall, while windows with patterned valances provide natural light. Built-in cabinetry with sink and small appliances line the opposite wall.
Intimate dining space with round gray wooden table surrounded by upholstered chairs, illuminated by a large nautical-style pendant light with brass accents. A prominent landscape painting depicting marshland and waterways dominates one wall, while windows with patterned valances provide natural light. Built-in cabinetry with sink and small appliances line the opposite wall. Cottage 3 dining area with marsh landscape artwork | Photo: Better Living

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

Elegant white ceramic plate featuring house-made pasta topped with chunks of fresh lobster meat, crispy golden pancetta pieces, and fresh herbs. A silver fork rests beside the dish, and the pasta appears to be in a light sauce with visible herbs and pancetta creating textural contrast against the tender lobster and pasta.
Elegant white ceramic plate featuring house-made pasta topped with chunks of fresh lobster meat, crispy golden pancetta pieces, and fresh herbs. A silver fork rests beside the dish, and the pasta appears to be in a light sauce with visible herbs and pancetta creating textural contrast against the tender lobster and pasta.
 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

Artfully plated breakfast dish featuring perfectly poached egg with runny golden yolk atop rösti potatoes, smoked salmon, and sliced avocado. The white ceramic plate is garnished with microgreens and colorful edible flowers, with bright yellow yolk creating dramatic color contrast. Professional fine dining presentation demonstrates culinary attention to detail.
Artfully plated breakfast dish featuring perfectly poached egg with runny golden yolk atop rösti potatoes, smoked salmon, and sliced avocado. The white ceramic plate is garnished with microgreens and colorful edible flowers, with bright yellow yolk creating dramatic color contrast. Professional fine dining presentation demonstrates culinary attention to detail. Poached egg and smoked salmon breakfast at The Oak Room | Photo: Better Living

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

Intimate two-person dining table set with white linens, wine glasses, and formal place settings positioned beside large windows overlooking Oak Creek. The "Overcomer" yacht is visible at the dock, while warm evening light filters through the space. Professional table setting and scenic water views create an elegant fine dining atmosphere.
Intimate two-person dining table set with white linens, wine glasses, and formal place settings positioned beside large windows overlooking Oak Creek. The "Overcomer" yacht is visible at the dock, while warm evening light filters through the space. Professional table setting and scenic water views create an elegant fine dining atmosphere. Waterfront dining room table at The Oak Room with sunset yacht views | Photo: Better Living

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.

Artfully plated tuna tartare on white ceramic plate featuring diced raw tuna mixed with sesame seeds, lime, and tamari, topped with bright green caviar and sliced cuvumbers. The dish is accompanied by cucumber ribbons, avocado mousse dollops, and a golden crispy wonton chip. Two forks frame the colorful presentation on a warm wood table surface.
Artfully plated tuna tartare on white ceramic plate featuring diced raw tuna mixed with sesame seeds, lime, and tamari, topped with bright green caviar and sliced cuvumbers. The dish is accompanied by cucumber ribbons, avocado mousse dollops, and a golden crispy wonton chip. Two forks frame the colorful presentation on a warm wood table surface. Tuna tartare with avocado mousse and crispy wonton | Photo: Better Living

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.

Sophisticated dinner plate featuring sliced duck breast cooked to perfect medium-rare with pink interior, accompanied by bright orange sweet potato puree, seared royal trumpet mushrooms with crosshatch scoring, pickled blackberries, and decorative microgreens. Rich brown port wine reduction sauce pools around the elements on the pristine white ceramic plate.
Sophisticated dinner plate featuring sliced duck breast cooked to perfect medium-rare with pink interior, accompanied by bright orange sweet potato puree, seared royal trumpet mushrooms with crosshatch scoring, pickled blackberries, and decorative microgreens. Rich brown port wine reduction sauce pools around the elements on the pristine white ceramic plate. Duck breast with sweet potato puree and royal trumpet mushrooms | Photo: Better Living

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.

White ceramic ramekin containing strawberry crisp dessert topped with vanilla ice cream and garnished with fresh strawberries and crumble topping. A spoon holds a bite of the dessert showing the layered textures. In the background, a chocolate martini with rich brown color and chocolate rim garnish sits on the signature "1902" coaster.
White ceramic ramekin containing strawberry crisp dessert topped with vanilla ice cream and garnished with fresh strawberries and crumble topping. A spoon holds a bite of the dessert showing the layered textures. In the background, a chocolate martini with rich brown color and chocolate rim garnish sits on the signature "1902" coaster. Strawberry crisp dessert with vanilla ice cream and chocolate martini | Photo: Better Living

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

Elegant hotel bar with rich dark wood cabinetry, marble countertop, and three large nautical-style pendant lights with cream shades and brass hardware. Wine bottles line built-in shelving, wine glasses hang from overhead racks, and decorative tree motif provides artistic backdrop. Two modern bar stools with curved backs face the professionally equipped bar station.
Elegant hotel bar with rich dark wood cabinetry, marble countertop, and three large nautical-style pendant lights with cream shades and brass hardware. Wine bottles line built-in shelving, wine glasses hang from overhead racks, and decorative tree motif provides artistic backdrop. Two modern bar stools with curved backs face the professionally equipped bar station. The Oak Room bar featuring nautical pendant lighting | Photo: Better Living

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.

Hands squeezing fresh lemon peel over a pale yellow cocktail in a martini glass with salted rim. The citrus oils are visibly misting as they're expressed from the bright yellow lemon peel. The drink sits on a distinctive coaster marked "1902" referencing the hotel's founding year, positioned on a marble bar surface against a dark background.
Hands squeezing fresh lemon peel over a pale yellow cocktail in a martini glass with salted rim. The citrus oils are visibly misting as they're expressed from the bright yellow lemon peel. The drink sits on a distinctive coaster marked "1902" referencing the hotel's founding year, positioned on a marble bar surface against a dark background. Fresh lemon zest garnish for a Lemon Drop cocktail at The Oaks bar | Photo: Better Living

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

Colorful Victorian-era storefront with red and white striped trim and curved corner entrance displaying "WYE" signage. Two life-sized painted jockey statues in racing silks (one in red and blue, one in yellow and green) flank the entrance. Brick sidewalks, decorative planters with flowers, and traditional architecture create a charming small-town shopping atmosphere.
Colorful Victorian-era storefront with red and white striped trim and curved corner entrance displaying "WYE" signage. Two life-sized painted jockey statues in racing silks (one in red and blue, one in yellow and green) flank the entrance. Brick sidewalks, decorative planters with flowers, and traditional architecture create a charming small-town shopping atmosphere. Shopping in Easton, MD | Photo: Better Living

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

Charming restaurant exterior featuring a wraparound covered porch with white columns and green-and-white striped awning. The building has classic brick architecture with a prominent circular "Bistro St. Michaels" sign. Black metal patio furniture is arranged on the brick sidewalk, and decorative flower boxes with trailing plants add color to the white porch railings.
Charming restaurant exterior featuring a wraparound covered porch with white columns and green-and-white striped awning. The building has classic brick architecture with a prominent circular "Bistro St. Michaels" sign. Black metal patio furniture is arranged on the brick sidewalk, and decorative flower boxes with trailing plants add color to the white porch railings. Bistro St. Michaels restaurant exterior in historic downtown | Photo: Better Living

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.

A white ceramic plate showcasing expertly plated braised beef short rib sliced to reveal tender, pink interior meat. The dish is topped with golden-brown crispy fried onions and accompanied by vibrant green vegetables including broccolini. Rich, glossy brown sauce pools around the meat, and the presentation demonstrates fine dining plating techniques on a granite countertop.
A white ceramic plate showcasing expertly plated braised beef short rib sliced to reveal tender, pink interior meat. The dish is topped with golden-brown crispy fried onions and accompanied by vibrant green vegetables including broccolini. Rich, glossy brown sauce pools around the meat, and the presentation demonstrates fine dining plating techniques on a granite countertop. Braised beef short rib with crispy onions at Bistro St. Michaels | Photo: Better Living

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.

See also

Split image showing luxury car transport services - left side features a red Lamborghini with scissor doors open in an upscale garage setting, right side shows a red SUV loaded on a multi-level car carrier trailerSplit image showing luxury car transport services - left side features a red Lamborghini with scissor doors open in an upscale garage setting, right side shows a red SUV loaded on a multi-level car carrier trailer

Lunch at Tiger Lily Easton

Vibrant restaurant interior featuring dark green palm leaf wallpaper, fishing net ceiling decoration with colorful paper lanterns, and red neon "Tiger Lily" sign as focal point. The space includes reclaimed wood bar seating, round tables, and eclectic lighting creating a fun, tropical atmosphere. An open kitchen and dining room are visible in the background, with string lights and tiki-inspired design elements throughout.
Vibrant restaurant interior featuring dark green palm leaf wallpaper, fishing net ceiling decoration with colorful paper lanterns, and red neon "Tiger Lily" sign as focal point. The space includes reclaimed wood bar seating, round tables, and eclectic lighting creating a fun, tropical atmosphere. An open kitchen and dining room are visible in the background, with string lights and tiki-inspired design elements throughout. Tiger Lily restaurant interior with tropical tiki-bar atmosphere | Photo: Better Living

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.

Silver aluminum takeout container holding three soft tacos filled with adobo-marinated pork, topped with fresh cilantro, white shredded cheese, and green salsa verde. A lime wedge provides citrus accent, and the tacos are garnished with additional herbs and appear to include pineapple pieces characteristic of al pastor preparation.
Silver aluminum takeout container holding three soft tacos filled with adobo-marinated pork, topped with fresh cilantro, white shredded cheese, and green salsa verde. A lime wedge provides citrus accent, and the tacos are garnished with additional herbs and appear to include pineapple pieces characteristic of al pastor preparation. Al Pastor tacos Tiger Lily Easton | Photo: Better Living

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

Birdwatching equipment arranged on neutral carpet including black binoculars, blue "Chesapeake Bay Nature of the Estuary Field Guide" book, and red "Birds of Maryland & Delaware Field Guide" featuring a bright red cardinal on the cover. The guides are specifically focused on local Chesapeake Bay area wildlife.
Birdwatching equipment arranged on neutral carpet including black binoculars, blue "Chesapeake Bay Nature of the Estuary Field Guide" book, and red "Birds of Maryland & Delaware Field Guide" featuring a bright red cardinal on the cover. The guides are specifically focused on local Chesapeake Bay area wildlife. Birdwatching amenities at The Oaks Waterfront Hotel | Photo: Better Living

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

Circular stone fire pit surrounded by multiple wooden Adirondack chairs arranged on flagstone patio, with flames visible in the center. The scene is illuminated against dark evening sky, with mature trees and cottage lights creating ambient background lighting. Additional seating areas are visible in the distance, emphasizing the social nature of this outdoor gathering space.
Circular stone fire pit surrounded by multiple wooden Adirondack chairs arranged on flagstone patio, with flames visible in the center. The scene is illuminated against dark evening sky, with mature trees and cottage lights creating ambient background lighting. Additional seating areas are visible in the distance, emphasizing the social nature of this outdoor gathering space. Evening fire pit gathering area with Adirondack chairs | Photo: Better Living

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

Luxury white yacht with enclosed cabin and dark trim moored at wooden dock during golden hour. The 40-foot vessel features multiple windows, professional rigging, and classic yacht styling. In the background, the hotel's white buildings with multiple levels and balconies are visible across the manicured waterfront lawn dotted with white outdoor furniture.
Luxury white yacht with enclosed cabin and dark trim moored at wooden dock during golden hour. The 40-foot vessel features multiple windows, professional rigging, and classic yacht styling. In the background, the hotel's white buildings with multiple levels and balconies are visible across the manicured waterfront lawn dotted with white outdoor furniture. The Hinckley yacht “Overcomer” at The Oaks private pier | Photo: Better Living

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

Person wearing plush white terrycloth bathrobe embroidered with "The Oaks" logo and decorative tree design, holding a partially eaten chocolate chip cookie while standing by large windows overlooking green grounds with white fencing. The scene captures the relaxed, pampered atmosphere of the waterfront hotel experience.
Person wearing plush white terrycloth bathrobe embroidered with "The Oaks" logo and decorative tree design, holding a partially eaten chocolate chip cookie while standing by large windows overlooking green grounds with white fencing. The scene captures the relaxed, pampered atmosphere of the waterfront hotel experience. Luxury robe and homemade cookies at The Oaks cottage | Photo: Better Living

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

Six cream-colored cruiser bikes with brown leather seats lined up along white wooden fencing, with vibrant flower beds in foreground. Beyond lies expansive green lawn leading to waterfront with white Adirondack chairs under umbrellas, boat dock with covered pavilion, and luxury yacht moored at pier. Trees frame the scenic Chesapeake Bay setting.
Six cream-colored cruiser bikes with brown leather seats lined up along white wooden fencing, with vibrant flower beds in foreground. Beyond lies expansive green lawn leading to waterfront with white Adirondack chairs under umbrellas, boat dock with covered pavilion, and luxury yacht moored at pier. Trees frame the scenic Chesapeake Bay setting. Waterfront lawn with complimentary bicycles and yacht access | Photo: Better Living

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

Two modern farmhouse-style cottages with white siding, dark roofs, and covered porches set on expansive green lawn. Vibrant pink roses bloom in the foreground, and mature trees frame the background. A paved walkway connects the buildings, and white outdoor furniture is visible on the lawn, creating an idyllic waterfront resort setting.
Two modern farmhouse-style cottages with white siding, dark roofs, and covered porches set on expansive green lawn. Vibrant pink roses bloom in the foreground, and mature trees frame the background. A paved walkway connects the buildings, and white outdoor furniture is visible on the lawn, creating an idyllic waterfront resort setting. Waterfront cottages with rose gardens at The Oaks | Photo: Better Living

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.

Plan Your Escape to The Oaks Waterfront Hotel

Relax by the water, enjoy exceptional dining, and unwind in the heart of Maryland’s Eastern Shore.

Book Your Stay at The Oaks!

Directions To The Oaks

 

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