5 Most Romantic Hotels in Maryland & the Eastern Shore

Most couples searching for romantic Maryland getaways miss the best properties entirely. While chain hotels dominate search results, the Eastern Shore hides intimate inns with private cottages, waterfront boutique hotels with impeccable service, and modern retreats where every detail anticipates what couples need. After staying at dozens of Maryland properties, these five stand out for creating genuine romantic experiences.

Why the Eastern Shore Dominates Maryland’s Romantic Hotel Scene

The Chesapeake Bay region delivers what couples actually want: seclusion without isolation, exceptional dining within walking distance, and settings that encourage you to slow down and reconnect.

Four of these five hotels sit on or near the water. That’s not coincidence. Waterfront locations – even in the winter,  provide sunset views, peaceful morning walks, and that sense of escape that makes romantic getaways work. The fifth – Brampton 1860 – trades water views for 35 acres of private estate grounds where you won’t see another soul if you don’t want to. But even here, the waterfront is just a 2 minute drive into quaint Chestertown.

From historic cottages with soaking tubs to modern suites with floor-to-ceiling bay views, each property earned its ranking through exceptional attention to couples, distinctive romantic amenities, and those intangible qualities that make you extend your checkout time.

Quick Comparison: Maryland’s Most Romantic Hotels

Hotel Location Price Range Best For

Brampton 1860	Chestertown	$$-$$$	Ultimate privacy & seclusion
The Wildset Hotel	St. Michaels	$$-$$$	Boutique charm & walkable town
The Oaks Waterfront	Easton	$$$	Intimate luxury & pampering
Hyatt Place Kent Narrows	Kent Narrows	$$	Waterfront views & dining scene
Merriweather Lakehouse	Columbia	$$-$$$	Modern lakefront & rooftop pool

1. Brampton 1860 – Chestertown: The Ultimate Romantic Escape

Inside Marley’s Cottage at Brampton 1860 | Photo: Better Living

What Makes Brampton 1860 Maryland’s Most Romantic Hotel

Brampton 1860 takes the top spot because it delivers something increasingly rare: genuine seclusion combined with thoughtful luxury.

The private cottages scattered across 35 acres create your own world. Marley’s Cottage, hidden behind an old barn’s red door, offers 1,000 square feet of complete privacy. The elevated bedroom overlooks a wood-burning fireplace. The screened porch features a deep Japanese soaking tub facing meadows where deer wander at dusk.

This isn’t a hotel where you’re steps from other guests. You’re tucked away in your own retreat, yet just a two-minute walk to the Manor House for farm-to-table breakfasts featuring eggs from Brampton’s chickens.

Marley’s Cottage: 1,000 square feet of private paradise | Photo: Better Living

Romantic Experiences at Brampton 1860

The magic happens in the details. Daily afternoon tea at 4:00 PM brings couples together in the Manor House over wine, fresh-baked pastries, and conversation with other guests and the passionate innkeepers, Dave and Hilari Rinehart.

The Signature Steampot dinner delivered to your cottage creates an unforgettable evening. Local crabs, shrimp, clams, sweet corn, and kielbasa arrive ready to enjoy on your private porch as the sun sets over the meadow.

Evenings by the fire pit under the stars. Morning walks through gardens at peak bloom. Fruit picking from the property’s trees. Every moment feels deliberately crafted for connection.

Summer evening magic at Brampton’s historic Manor House | Photo: Better Living

Why Couples Love Brampton 1860

The hands-on hosts make the difference. Dave and Hilari don’t just run Brampton – they care for it and share that passion with guests. Their enthusiasm for the property’s history, the Certified Wildlife Habitat designation, and creating memorable stays shows in every interaction.

Squeaky, the 14-year-old black cat who truly runs the place, adds unexpected charm. He’ll join you for dinner, follow you to breakfast, and make himself comfortable at the evening fire pit like the seasoned host he is.

Perfect for: Anniversary celebrations, proposals, couples who value privacy over proximity to nightlife, history lovers, nature enthusiasts, and anyone seeking a true escape.

Read Our Complete Brampton 1860 Review

2. The Wildset Hotel – St. Michaels: Boutique Romance in America’s Most Beautiful Town

A beautiful morning at The Wildset Hotel | Photo: Better Living

What Makes The Wildset Hotel Irresistibly Romantic

The Wildset captures that sweet spot between intimate boutique hotel and prime location. Set in three renovated 19th-century buildings in the heart of St. Michaels – Conde Nast’s “Most Beautiful Town in Maryland” – you’re steps from waterfront dining, antique shops, and picturesque streets.

Each of the 34 suites brings its own character. Modern farmhouse decor meets Scandinavian simplicity. Parachute bedding ensures restful sleep. Grown Alchemist bath products add spa-quality touches. Premium suites feature fireplaces, private balconies, and deep soaking tubs perfect for unwinding together.

Room 102 at The Wildset Hotel | Photo: Better Living

The magic extends beyond your room. Complimentary cruiser bikes invite exploration of the 1.3-mile St. Michaels Nature Trail. Evening s’mores kits and a crackling fire pit create opportunities to connect under the stars.

Romantic Dining at Ruse

The onsite restaurant Ruse deserves special mention. Named in honor of St. Michaels being “The Town that Fooled the British,” this modern American seafood restaurant serves some of the best food we’ve experienced at any hotel.

The roasted local oysters with garlic breadcrumbs and urfa biber are buttery perfection. Seared scallops with local pea puree showcase the season’s best. The intimate patio under twinkling lights at sunset creates exactly the atmosphere you want for a romantic dinner.

The Wildset offers free s’mores kits and a nightly firepit | Photo: Better Living

Why Couples Choose The Wildset

Location matters. You can walk to exceptional restaurants like Bistro St. Michaels and Carpenter Street Saloon, browse antique shops, and enjoy sunset views at the marina. Yet you return to a peaceful, beautifully designed retreat.

The nightly fire pit gatherings strike a perfect balance. You can mingle with other couples or claim a quiet corner for yourselves. Either way, you’re surrounded by flickering flames and the peaceful Eastern Shore evening.

Perfect for: Couples who want boutique luxury without isolation, foodies seeking exceptional dining, active couples who enjoy biking and walking, anyone charmed by historic small-town atmosphere.

Explore St. Michaels: Your Complete Travel Guide

3. The Oaks Waterfront Hotel – Easton: Intimate Luxury with Four Seasons Service

Cottage 3 bedroom with woodland views and luxury amenities | Photo: Better Living

What Makes The Oaks Waterfront Hotel Special

With only 11 rooms in the main building and 4 waterfront cottages, The Oaks delivers something increasingly rare: the attentiveness of a luxury property combined with genuine warmth.

The level of service rivals The Four Seasons or Ritz-Carlton. Fresh flowers appear daily throughout the property. The restaurant looks picture-perfect at every meal. Premium amenities fill the rooms – quality furnishings, exceptional linens, plush robes. Yet the staff greets you by name and makes you feel like welcomed friends rather than hotel guests.

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

Cottage 3, where we stayed, showcases this perfectly. The spacious layout includes a king bed with luxury linens, heated bathroom floors, a deep soaking tub, and a covered porch overlooking Oak Creek. The complimentary chocolate chip cookies baked onsite became a daily highlight.

Romantic Dining at The Oak Room

Chef Dave’s cuisine at The Oak Room rivals much larger hotels. The Corn and White Truffle Agnolotti with butter-poached lobster and crisp prosciutto is pure indulgence. Maryland Crab Cakes over forest mushroom risotto highlight the region’s best ingredients.

Sujoy’s cocktail artistry at the bar transforms drinks into theater. Each cocktail is crafted right in front of you – from the Chocolate Espresso Martini with freshly grated chocolate to the perfectly balanced Spicy Margarita.

The intimate dining room with water views seats just enough couples to feel special without feeling crowded. Tuesday through Thursday dinner service creates a more exclusive atmosphere.

Waterfront dining room table at The Oak Room with sunset yacht views | Photo: Better Living

Why The Oaks Stands Out for Romance

The 10-acre waterfront property provides space to breathe. Adirondack chairs dot the lawn facing the water. The evening fire pit brings couples together under the stars. The 40-foot Hinckley yacht “Overcomer” waits at the private pier for sunset cruises (weather permitting).

The intimate size means you’ll likely meet other guests naturally – at the fire pit, during breakfast, or over cocktails. We had wonderful conversations with both fellow travelers and staff throughout our stay. Yet you never feel crowded.

Golf cart rides across the grounds and a luxury SUV for shopping and dining trips in nearby Easton and St. Michaels add convenience without fuss.

Perfect for: Couples seeking luxury without stuffiness, foodies who appreciate exceptional cuisine and craft cocktails, travelers who value attentive service, anyone wanting to be thoroughly pampered.

Read Our Complete Oaks Waterfront Hotel Review

4. Hyatt Place Kent Narrows & Marina – Kent Narrows: Modern Waterfront Romance

Stunning sunset views from Hyatt Place Kent Narrows | Photo: Better Living

What Makes Hyatt Place Kent Narrows Romantically Appealing

Kent Narrows remains one of Maryland’s best-kept secrets – a laid-back waterfront destination surrounded by stunning Chesapeake Bay views in almost every direction. The Hyatt Place sits at the heart of Fisherman’s Village, where you can walk to exceptional seafood restaurants and dockside bars.

The 120 modern rooms bring coastal-inspired serenity with natural woods and calming blues and grays. Book a waterfront suite with a private balcony to watch boats cruise by on Prospect Bay. The spacious suites include kitchenettes, 55-inch flat screens, and plush bedding.

The view from the balcony suites at Hyatt Place Kent Narrows | Photo: Better Living

What sets this property apart is the atmosphere. While families visit, the vibe skews adult. The expansive waterfront deck, fire pit at sunset, and proximity to lively but not rowdy dockside dining creates the perfect balance for couples.

Romantic Waterfront Dining Within Walking Distance

Location makes or breaks a romantic getaway, and Hyatt Place Kent Narrows nails it. You’re steps from Fisherman’s Inn with its award-winning Coconut Cream Pie and collection of 300+ antique oyster plates. The iconic Fisherman’s Crab Deck delivers the authentic Maryland experience – fresh steamed crabs, orange crushes, and sunset views.

Big Owl Tiki Bar next door brings Key West vibes to the Chesapeake. Soft shell crab tacos, tropical cocktails, and live music create the perfect casual evening. The famous Kent Narrows Nutty Buddy ice cream cone is mandatory.

Walk back to your waterfront suite after dinner and enjoy the bay views from your private balcony. Or grab drinks from The Placery lobby bar and relax by the fire pit as the sun sets.

The living and dining area in a waterfront suite at Hyatt Place Kent Narrows | Photo: Better Living

Why Couples Choose Hyatt Place Kent Narrows

The complimentary breakfast served on the dockside terrace starts each day right. Fresh coffee, hot items, and those stunning water views create a peaceful morning routine.

The 24/7 fitness center, indoor pool overlooking the marina, and proximity to hiking and biking trails appeal to active couples. Yet the relaxed pace of Kent Narrows makes it equally perfect for doing absolutely nothing but watching boats go by.

The 40 dock slips behind the property mean boating couples can arrive by water. And the adult-focused atmosphere (without being couples-only) strikes the right balance for a romantic escape.

Perfect for: Couples who love waterfront dining and sunset views, boating enthusiasts, travelers seeking modern comfort with authentic Chesapeake Bay character, anyone who values walkability to restaurants and bars.

Discover Kent Narrows: Maryland’s Waterfront Hidden Gem

5. Merriweather Lakehouse Hotel – Columbia: Modern Lakefront Luxury

The living area in the Presidential Suite at Merriweather Lakehouse Hotel | Photo: Better Living

What Makes Merriweather Lakehouse Hotel Romantic

This 212-room Marriott Autograph Collection property brings contemporary luxury to Lake Kittamaqundi’s shores. The floor-to-ceiling windows throughout create an ever-present connection to the water – from the lobby to the hallways to your room.

Lake view rooms with private balconies deliver the full experience. Watching winter birds on the partially frozen lake from your balcony with morning coffee creates surprisingly intimate moments. The separate living areas in suites provide space to truly relax together after exploring Columbia or hiking the 1.4-mile lake trail.

The bedroom in the Presidential Suite at Merriweather Lakehouse Hotel | Photo: Better Living

The rooftop pool (open Memorial Day through Labor Day) and Eagle Watch Lounge add resort-style amenities during summer visits. This transforms the property into an ideal warm-weather romantic escape.

Exceptional Dining at lak Restaurant

The onsite restaurant lak (pronounced “lake”) serves cuisine that rivals standalone fine dining establishments. The Maryland Crab Cakes over creamy risotto showcase local ingredients beautifully. Corn and White Truffle Agnolotti with a huge piece of lobster claw is pure indulgence.

The Rookery Bar crafts creative cocktails with quality spirits. Floor-to-ceiling windows ensure you never lose sight of the lake, even while dining.

The complimentary breakfast from 8:30-9:30 AM features elevated options like Poached Egg with Smoked Salmon over rosti potatoes, Eastern Shore Omelette with jumbo lump crab, and French Toast with Chantilly cream. Starting the day overlooking the water sets the perfect tone.

A panoramic view from the hotel of Lake Kittamaqundi | Photo: Better Living

Why Merriweather Lakehouse Appeals to Couples

The location just 15 minutes from BWI Airport makes spontaneous romantic weekends easy. Columbia’s downtown offers shopping at the Mall of Columbia, dining in the trendy Merriweather District, and concerts at the legendary Merriweather Post Pavilion (15-minute walk).

Free parking is rare at luxury properties. The pet-friendly policy (no extra fees) means furry companions can join the escape. The 1.4-mile Lake Kittamaqundi trail provides peaceful walks where you’ll spot herons, ospreys, and even bald eagles.

The modern design and Marriott Bonvoy benefits appeal to couples who appreciate contemporary luxury over historic charm. The 24-hour fitness center with Peloton bikes and quality equipment means no guilt about skipping workouts.

Perfect for: Couples who prefer modern luxury over historic properties, summer visits when the rooftop pool is open, pet owners, nature lovers and birdwatchers, travelers wanting easy access to DC/Baltimore, Marriott Bonvoy members.

Read Our Complete Merriweather Lakehouse Hotel Review

Where to Dine: Romantic Restaurants at Each Hotel

Exceptional dining plays a crucial role in romantic getaways. Here’s where to eat at each property:

Brampton 1860 Dining Options

Onsite: Farm-to-table breakfast included with stay, afternoon tea at 4 PM, Signature Steampot dinner delivered to cottage. Seasonal options also availble.

Nearby in Chestertown: The Kitchen at the Imperial (Chef Steve Quigg’s farm-to-table fine dining), Crow Vineyard (wine tasting and patio dining)

The Wildset Hotel Dining Options

Onsite: Ruse Restaurant (modern American seafood, dinner and brunch)

Nearby in St. Michaels: Bistro St. Michaels (upscale French-Southern fusion), Carpenter Street Saloon (historic tavern), Foxy’s Harbor Grille (waterfront casual)

The Oaks Waterfront Hotel Dining Options

Onsite: The Oak Room (fine dining, Tuesday-Thursday evenings), The Rookery Bar & Lounge (craft cocktails), The Osprey Cafe (gourmet coffee and pastries)

Nearby in Easton/St. Michaels: Bistro St. Michaels, Tiger Lily Easton (creative tacos and fusion)

Hyatt Place Kent Narrows Dining Options

Onsite: The Placery (lobby bar with light bites), complimentary breakfast buffet

Walking Distance in Fisherman’s Village: Fisherman’s Inn (upscale seafood), Fisherman’s Crab Deck (casual waterfront crabs), Big Owl Tiki Bar (tropical drinks and tacos)

Nearby: Bridges Restaurant (Caribbean-inspired), Dock House (modern coastal), Harris Crab House (traditional Maryland seafood)

Merriweather Lakehouse Dining Options

Onsite: lak Restaurant (American fine dining), The Rookery Bar (craft cocktails), The Osprey Cafe (coffee and pastries)

Nearby in Columbia: Merriweather District restaurants, Mall of Columbia dining options

How to Choose the Right Romantic Maryland Hotel

Choose Brampton 1860 if you want: Complete privacy in a secluded cottage, historic charm, farm-to-table dining, nature immersion, the ultimate romantic escape from reality.

Choose The Wildset Hotel if you want: Boutique luxury in a walkable historic town, excellent onsite dining at Ruse, easy access to shops and restaurants, modern farmhouse aesthetic, evening s’mores by the fire.

Choose The Oaks Waterfront Hotel if you want: To be pampered with Four Seasons-level service, intimate property with only 15 accommodations, exceptional cuisine at The Oak Room, waterfront tranquility, adults-only atmosphere.

Choose Hyatt Place Kent Narrows if you want: Modern waterfront suites with bay views, walkable access to multiple restaurants and bars, adult-focused vibe, spectacular sunsets, best value for waterfront romance.

Choose Merriweather Lakehouse Hotel if you want: Contemporary lakefront luxury, summer rooftop pool access, proximity to DC/Baltimore, pet-friendly accommodations, hiking and nature right outside your door.

Best Time to Visit Maryland for Romance

Spring (April-May): Perfect weather for outdoor activities, fewer crowds than summer, blooming gardens at historic properties like Brampton 1860, comfortable temperatures for exploring towns like St. Michaels.

Summer (June-August): Peak season for waterfront properties, rooftop pool open at Merriweather Lakehouse, outdoor dining at its finest, sunset cruises and water activities, live music at Kent Narrows restaurants.

Fall (September-November): Spectacular foliage, harvest season at local vineyards, comfortable hiking weather, cozy fireplaces at The Wildset, fewer crowds after Labor Day.

Winter (December-February): Lowest rates of the year, cozy romance by the fire, intimate atmosphere, hot chocolate and s’mores, perfect for couples seeking quiet connection.

Planning Your Romantic Maryland Getaway

How far in advance to book: For weekend stays at any of these properties, book 4-6 weeks ahead minimum. Special occasions (Valentine’s Day, anniversaries) and peak fall foliage season require 2-3 months advance booking. Cottages at Brampton 1860 and The Oaks book especially quickly.

Recommended length of stay: Two nights minimum allows you to settle in and truly relax. Three nights lets you explore nearby attractions without rushing. All five properties reward longer stays with their peaceful settings.

What to pack: Comfortable walking shoes for trails and town exploration, layers for changing weather, binoculars for birdwatching (especially at Brampton 1860 and Merriweather Lakehouse), camera for stunning sunset photos, appetites for incredible dining.

Getting there: All five properties are within 1-2 hours of Baltimore, Washington DC, and Philadelphia. Brampton 1860 and The Wildset are closest to each other (20 minutes apart) for couples wanting to experience multiple properties. Kent Narrows sits perfectly between the Eastern Shore’s attractions.

Make Your Maryland Romance Unforgettable

Maryland’s Eastern Shore and surrounding regions deliver romance in distinctive ways. From Brampton 1860’s secluded cottages to The Oaks’ intimate pampering, from The Wildset’s boutique charm to Hyatt Place Kent Narrows’ waterfront sunsets, each property creates its own romantic magic.

The best romantic hotel depends on what matters most to you as a couple. Total privacy and nature? Brampton wins. Boutique luxury in a charming town? The Wildset delivers. Being thoroughly pampered? The Oaks excels. Waterfront dining and sunset views? Hyatt Place Kent Narrows nails it. Modern lakefront luxury? Merriweather Lakehouse satisfies.

What they all share is genuine attention to couples, exceptional dining, beautiful settings, and that indefinable quality that makes you want to linger just a bit longer before checking out.

Your perfect Maryland romantic escape is waiting. The only question is which one to book first.

Frequently Asked Questions About Romantic Hotels in Maryland

What is the most romantic hotel in Maryland?

Brampton 1860 in Chestertown takes the top spot for most romantic hotel in Maryland. The private cottages offer complete seclusion on a 35-acre estate, with features like Japanese soaking tubs, wood-burning fireplaces, and private porches overlooking meadows. The combination of privacy, historic charm, farm-to-table dining, and attentive hosts creates an unmatched romantic atmosphere.

Which Maryland hotel is best for anniversaries?

The Oaks Waterfront Hotel in Easton is ideal for anniversaries. With only 15 total accommodations, the intimate property provides Four Seasons-level service and pampering. Private waterfront cottages, exceptional dining at The Oak Room, heated bathroom floors, and thoughtful touches like fresh daily flowers create a celebration-worthy experience. The staff’s genuine warmth makes special occasions feel truly special.

Where should couples stay in St. Michaels, Maryland?

The Wildset Hotel is the best choice for couples in St. Michaels. The boutique property offers 34 unique suites in renovated 19th-century buildings right in the heart of town. You’re steps from waterfront dining, antique shops, and the harbor, yet return to modern farmhouse luxury with fireplaces, soaking tubs, and complimentary bikes. The onsite restaurant Ruse serves exceptional cuisine, and evening s’mores by the fire pit add romantic touches.

What is the best waterfront romantic hotel on the Chesapeake Bay?

Hyatt Place Kent Narrows offers the best combination of waterfront location, value, and romantic atmosphere on the Chesapeake Bay. The modern waterfront suites with private balconies provide stunning bay views and sunsets. You can walk to multiple excellent restaurants and bars in Fisherman’s Village, creating easy romantic evenings. The adult-focused atmosphere, expansive deck space, and fire pit overlooking the water enhance the romantic setting.

Do any romantic Maryland hotels allow pets?

Yes, both Merriweather Lakehouse Hotel and Hyatt Place Kent Narrows are pet-friendly with no additional pet fees. The Oaks Waterfront Hotel also welcomes well-behaved dogs. Some cottages at Brampton 1860 (Russell’s Cottage and Robin’s Nest) accept pets, though these book quickly. Always inform the property when booking that you’re traveling with a pet.

Which Maryland hotel has the best romantic dining?

This depends on your preference. Ruse at The Wildset Hotel serves creative modern American seafood in an intimate setting. The Oak Room at The Oaks Waterfront Hotel offers elevated cuisine with Chef Dave’s artistry and Sujoy’s craft cocktails. Brampton 1860’s Signature Steampot delivered to your private cottage creates a uniquely romantic dining experience. All three provide exceptional food in romantic atmospheres.

What is the most secluded romantic hotel in Maryland?

Brampton 1860 offers the most seclusion. Private cottages scattered across 35 acres provide complete privacy, yet you’re just a short walk to the Manor House for meals and amenities. Marley’s Cottage, hidden behind a barn’s red door, exemplifies this seclusion – you feel like you’ve discovered a secret world. The natural surroundings, Certified Wildlife Habitat designation, and lack of nearby development enhance the secluded atmosphere.

Are these Maryland romantic hotels good for proposals?

Absolutely. Brampton 1860’s private cottages and grounds offer intimate settings for proposals. The Oaks Waterfront Hotel’s yacht sunset cruises (weather permitting) create memorable proposal moments. The Wildset Hotel’s fire pit area under the stars or The Rookery Bar’s sunset views at Merriweather Lakehouse both work beautifully. Contact properties in advance – they’re experienced with proposals and can help coordinate special touches.

Which Maryland hotel is best for a romantic weekend from DC or Baltimore?

Merriweather Lakehouse Hotel in Columbia is most convenient, just 15 minutes from BWI Airport and under an hour from both DC and Baltimore. This makes spontaneous romantic weekends easy. The modern luxury, floor-to-ceiling lake views, and rooftop pool (summer only) provide a complete escape despite the proximity to cities. Free parking is an added bonus.

Do these romantic hotels have minimum stay requirements?

Weekend minimum stays vary by property and season. Brampton 1860 and The Oaks often require two-night minimums on weekends during peak season. The Wildset Hotel, Hyatt Place Kent Narrows, and Merriweather Lakehouse typically don’t have minimums, though this can change during holidays or special events. Always check directly with properties when booking, especially for holiday weekends.

What makes the Eastern Shore good for romantic getaways?

The Eastern Shore combines proximity to major cities with a slower pace of life. Historic towns like St. Michaels and Chestertown offer walkable charm without crowds. Waterfront locations provide stunning sunset views. Farm-to-table dining showcases the region’s bounty. The Chesapeake Bay creates a scenic backdrop for every moment. Close enough for weekend trips, yet far enough to feel like a true escape.

Can you visit multiple romantic Maryland hotels in one trip?

Absolutely. Brampton 1860 in Chestertown and The Wildset Hotel in St. Michaels are only 20 minutes apart, making them perfect for a split-stay romantic tour. The Oaks in Easton is 15 minutes from St. Michaels. Hyatt Place Kent Narrows sits between these properties. A 4-5 day trip could include stays at 2-3 properties, experiencing different romantic styles while exploring the Eastern Shore.

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