Weekend Getaways in Maryland
Plan a romantic weekend trip in Maryland where you can choose from country inns, quiet B&Bs and full-service resorts.
“We could be home by dinner… but I don’t want to be.” That’s the feeling I’ve carried on every Maryland weekend escape, close enough to keep it simple, far enough to feel like you’ve stepped outside your own life for a while.
From misty mountain mornings in the west to Chesapeake sunrises in the east, Maryland quietly packs in so much variety. Fishing towns with weather-worn marinas, elegant inns on private coves, historic taverns where time slows down, each place offered a different kind of reset. I wasn’t chasing adventure. I was chasing quiet, charm, and places that reminded me how to breathe deeply again.
Best Weekend Getaways in Maryland for Couples:
Rod 'N' Reel Resort - 1 hour 10 minutes from Baltimore
“This feels like a town that still knows how to slow down.” I thought that as I walked the length of the North Beach boardwalk just after sunrise, the sky streaked in pinks and silvers behind docked boats.
Rod 'N' Reel Resort in Chesapeake Beach felt like part marina, part memory, easygoing, nostalgic, and tucked into its own rhythm. The room overlooked the bay, where gulls circled and fishermen cast off quietly in the early light.
What I Loved Most: Walking to the fishing pier before breakfast, then watching herons glide past from a wooden bench with a coffee in hand.
My highlight? Breakfast at the on-site waterfront restaurant. I ordered crab omelet and skillet potatoes. The crab was fresh and sweet, the eggs folded soft and warm. It smelled of butter, brine, and toast, and tasted like a calm morning in a coastal town should.
Plan your Rod 'N' Reel getaway:
- Address: 4165 Mears Ave, Chesapeake Beach, MD 20732
- Drive Time from DC: ~1 hour southeast
- Vibe: Casual waterfront resort with marina charm and retro heart
- Don’t Miss: Boardwalk strolls, fishing charters, spa treatments, bingo or live music in the lounge
- Best Time to Visit: Spring through fall for warm mornings and full bay views
- Cost: Rooms from ~$160/night
Wylder Hotel: Island Breezes & Bayfront Simplicity
“It smells like salt and old wood, like summer used to.” That was my first thought stepping out of the car at Wylder Hotel on Tilghman Island. The breeze carried briny air and quiet, just the sound of water tapping against the dock and a few laughing gulls overhead.
The hotel sits right on the edge of Knapps Narrows, where boats drift through like slow-moving postcards. My room had a wide porch, and I watched the water glimmer through slats of weathered railing. I felt unhurried, like I’d been given permission to let time stretch out.
What I Loved Most: Borrowing one of the retro bikes and riding along the narrow island roads, with fields on one side and the bay on the other.
My highlight? Dinner at Tickler’s Crab Shack. I had grilled rockfish with sweet corn and a lemony herb butter. The fish was tender and smoky; the scent reminded me of driftwood and sea grass warmed by sun. I lingered on the dock afterward, the last light gold on the water.
Plan your Wylder Tilghman escape:
- Address: 21551 Chesapeake Acc, Tilghman Island, MD 21671
- Drive Time from DC: ~2 hours east
- Vibe: Coastal vintage, laid-back, island-time retreat
- Don’t Miss: Dockside lounging, kayaking, outdoor fire pits, dinner at Tickler’s
- Best Time to Visit: Late spring through early fall for warm nights and boat-watching
- Cost: Rooms from ~$200/night
Annapolis Waterfront Hotel: Nautical Views & Historic Walks
“This city feels like it was built for strolling.” That thought came to me while wandering along the brick-lined streets just beyond the hotel, shops spilling over with charm, and masts clinking gently in the harbor breeze.
The Annapolis Waterfront Hotel sits right on the edge of Ego Alley, where sailboats parade in and out of the narrow inlet like they know they're being watched. My room had a window that framed the marina perfectly. I opened it to let in the salt air and the distant hum of downtown.
What I Loved Most: Walking out the front doors straight into the heart of the historic district, with its 18th-century houses, quiet side alleys, and the golden dome of the Maryland State House peeking over rooftops.
My highlight? Breakfast at Pusser’s Caribbean Grille downstairs. I had Chesapeake eggs benedict with lump crab and a side of stone-ground grits. The crab was buttery and clean, the hollandaise rich with a citrus kick. It smelled like lemon zest and sea breeze, and tasted like a weekend earned.
Plan your Annapolis Waterfront Hotel stay:
- Address: 80 Compromise St, Annapolis, MD 21401
- Drive Time from DC: ~45 minutes east
- Vibe: Polished marina-front hotel with walk-everywhere ease
- Don’t Miss: Waterfront dining, sailing tours, Naval Academy strolls, shops on Maryland Avenue
- Best Time to Visit: Spring through fall for boating season and mild weather
- Cost: Rooms from ~$260/night
St. Michaels Harbour Inn, Marina and Spa - 1 hour 30 minutes from Baltimore
“I could stay right here and do nothing all day.” That thought settled in as I sat on the balcony at Harbour Inn, watching kayakers glide past as the sky shifted from morning haze to bright blue.
The inn sits right on the edge of the harbor, tucked behind marinas and a short walk from downtown. Boats bobbed quietly, and everything, the water, the weathered docks, the distant church steeple, felt still. My room was spacious and breezy, the kind of place you don’t want to leave even when the town is calling.
What I Loved Most: Walking the trail along the waterfront in the early evening, past boats and crab shacks, the scent of salt and cedar in the air.
My highlight? Breakfast at the inn’s waterfront restaurant. I ordered cinnamon French toast with a side of local sausage. It smelled like vanilla and butter and tasted like comfort, crispy edges, soft inside, dusted with powdered sugar. Boats passed slowly as I ate, seagulls calling overhead.
Plan your Harbour Inn stay:
- Address: 101 N Harbour Rd, St. Michaels, MD 21663
- Drive Time from DC: ~1 hour 45 minutes east
- Vibe: Quiet marina retreat with town charm and waterside calm
- Don’t Miss: Spa treatments, boat rentals, walkable downtown, Chesapeake Bay Maritime Museum
- Best Time to Visit: Late spring to early fall for sunny strolls and outdoor dining
- Cost: Rooms from ~$200/night
The Reynolds Tavern - 35 minutes
“It smells like books and firewood in here.” That’s what I whispered to myself walking into The Reynolds Tavern, where creaky floors and candlelight made the centuries feel close.
Built in 1747, the tavern sits just across from the Maryland State House in downtown Annapolis. My room had a four-poster bed and slanted ceilings, and I felt like I’d stepped into a preserved page of the past, warm, lived-in, quietly grand.
What I Loved Most: Sitting in the walled garden out back, drinking tea under the trees while cicadas buzzed in the summer heat. It was peaceful in a way that felt both elegant and unpretentious.
My highlight? Afternoon tea in the Sly Fox Pub. I had freshly baked scones with cream and raspberry jam, alongside cucumber sandwiches and miniature lemon tarts. The scent of earl grey and warm pastry filled the room, and each bite was delicate and just sweet enough. I didn’t rush, it felt like time politely stepped aside.
Plan your Reynolds Tavern retreat:
- Address: 7 Church Circle, Annapolis, MD 21401
- Drive Time from DC: ~45 minutes east
- Vibe: Colonial elegance with a literary, tea-room soul
- Don’t Miss: Afternoon tea, garden patio, Sly Fox Pub, historic walking tours nearby
- Best Time to Visit: Spring or early fall for garden weather and fewer crowds
- Cost: Rooms from ~$195/night
Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore
“This feels like the kind of place where no one’s in a hurry.” That thought came to me as I floated in the infinity pool at Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina. The Choptank River stretched wide in front of me.
The resort is tucked just outside Cambridge, with sweeping waterfront views and the kind of easy luxury that doesn’t ask much, just that you relax. My room had a balcony overlooking the water and a breeze that carried in the scent of pine and salt.
What I Loved Most: Walking the nature trail that winds along the shore, then sipping coffee on the back lawn while boats glided by in the distance.
My highlight? Dinner at Blue Point Provision Company, the resort’s riverfront restaurant. I ordered the grilled rockfish with roasted vegetables. The fish was flaky and faintly smoky, the vegetables earthy and sweet. The air smelled of cedar and sea spray, and the sunset lit the sky in pinks and oranges. I sat still long after the plates were cleared.
Plan your Hyatt Regency Chesapeake Bay getaway:
- Address: 100 Heron Blvd, Cambridge, MD 21613
- Drive Time from DC: ~1 hour 45 minutes southeast
- Vibe: Family-friendly waterfront resort with room to roam
- Don’t Miss: Infinity pools, spa, 18-hole golf course, lawn games, nature trails
- Best Time to Visit: Summer for pool time and full resort activities; early fall for quiet beauty
- Cost: Rooms from ~$250/night
Wisp Resort
“I didn’t realize how quiet snow could be.” That’s what I was thinking as I stood at the top of the mountain, skis on, looking out over Deep Creek Lake dusted in white.
Wisp Resort, nestled in Maryland’s western mountains, feels like a seasonal switch, whether you come for the slopes or the lake. My room looked out over pine trees and ski lifts, and the air smelled like woodsmoke and fresh snow.
What I Loved Most: Riding the chairlift in silence as the wind brushed past and the landscape opened up all around. Even in summer, the views stretch far and wide.
My highlight? Breakfast at DC’s Bar & Restaurant inside the lodge. I had scrambled eggs with home fries and maple sausage. The potatoes were crisp and golden, the sausage sweet and savory. It smelled like syrup and butter, and warmed me right up after the mountain chill.
Plan your Wisp Resort getaway:
- Address: 296 Marsh Hill Rd, McHenry, MD 21541
- Drive Time from DC: ~3 hours west
- Vibe: Active mountain resort for snow days or summer lake escapes
- Don’t Miss: Skiing, snow tubing, mountain coaster, golf, lake kayaking
- Best Time to Visit: Winter for skiing, summer for lake adventures and hiking
- Cost: Rooms from ~$150/night
Ship Watch Inn
“I could listen to this water forever.” That’s what I was thinking as I rocked slowly on the front porch swing at Ship Watch Inn, the Sassafras River glinting in the late afternoon light.
The inn sits at the edge of Chesapeake City, where the canal meets the open river and time seems to move a little slower. My room had a private balcony overlooking the water, and in the quiet morning I watched tugboats pass like clockwork.
What I Loved Most: Walking the canal trail at sunrise, just me, the mist, and the sound of distant gulls cutting through the stillness.
My highlight? The homemade breakfast served in the cozy dining room. I had baked French toast with cinnamon apples and a side of crispy bacon. It smelled like brown sugar and butter, and the apples were warm and soft, each bite tasted like a September morning.
Plan your Ship Watch Inn stay:
- Address: 401 1st St, Chesapeake City, MD 21915
- Drive Time from DC: ~2 hours northeast
- Vibe: Riverside bed-and-breakfast with porch swing charm and canal-town quiet
- Don’t Miss: Walking the canal, browsing Chesapeake City’s antique shops, enjoying sunset from the inn’s deck
- Best Time to Visit: Spring and fall for mild weather and river views
- Cost: Rooms from ~$180/night, including breakfast
Brampton Bed & Breakfast Inn: Chestertown’s Quiet Estate Elegance
“A hush wrapped around me as I stepped onto the wrap-around porch.” That thought greeted me at Brampton 1860, the kind of stillness that invites you to pause and notice.
The inn sits on 35 acres of gardens, meadows, and woodland just south of Chestertown. I stayed in a spacious suite with plantation-style windows and modern comforts. The library’s fireplace crackled softly while I read, and walking paths wound through flowering lawns and shaded groves. Everything felt timeless and restful.
What I Loved Most: Afternoon tea on the terrace, with freshly baked pastries and soft conversation in the garden, the inn’s old-world hospitality felt effortlessly modern.
My highlight? Breakfast delivered to my room. I had croissant French toast with fresh fruit and scones with jam. The toast smelled buttery and nutty; the fruit bright and juicy. I ate slowly in my robe, then wandered across the lawn, content in the calm.
Plan your Brampton getaway:
- Address: 25227 Chestertown Road, Chestertown, MD 21620
- Drive Time from DC: ~2 hours east
- Vibe: Romantic, historic estate with modern comfort and quiet luxury
- Don’t Miss: Private cottages or manor-house rooms with fireplaces or soaking tubs, afternoon tea and snacks, garden walking paths, concierge recommendations
- Best Time to Visit: Spring through fall for full gardens and seasonal tranquility
- Cost: Rooms from ~$190–430/night, includes breakfast and tea
