Weekend Getaways in Maryland

I found that weekend getaways in Maryland are the perfect blend of coastal beauty, historic charm, and outdoor adventure, making them a great choice for a quick escape. Within just a short drive, you can explore bustling harbor towns, relax on sandy beaches, or retreat to the quiet of the mountains and countryside. What makes Maryland so appealing is its variety.

You might spend one weekend savoring fresh seafood in Annapolis, the next hiking in the Blue Ridge Mountains, or enjoying the vibrant arts and dining scene in Baltimore. Finding the right place to stay is part of the fun, whether it’s a waterfront inn, a cozy bed-and-breakfast, or a boutique hotel in the heart of the city. Here are some of the most unique Maryland getaways I came across that I think you’ll love for your next weekend adventure.

1. Rod 'N' Reel Resort - 1 hour 10 minutes from Baltimore

I drove 1 hour southeast from Washington, D.C. to Chesapeake Beach, a small resort town on the western shore of the Chesapeake Bay. My afternoon included a stroll along the bayside boardwalk, exploring the Chesapeake Beach Railway Museum, and grabbing fresh seafood with water views at a local crab house.

Rod 'N' Reel Resort in Chesapeake Beach, Maryland, is one of my favorite waterfront escapes along the Chesapeake Bay.

I love that it combines the charm of a seaside retreat with modern amenities, making it an underrated destination for both relaxation and adventure.

The resort sits right on the bay, and my favorite part was waking up to sunrise views over the water from my room’s private balcony.

I found the accommodations comfortable and inviting, with coastal-inspired décor that made the stay feel refreshing and peaceful.

Rod 'N' Reel is one of the best romantic escapes, with waterfront dining, spa treatments, and evenings spent walking along the marina.

Families will also love the wide range of activities, including fishing charters, boat rentals, a game room, and a pool that make it fun for all ages.

I especially enjoyed the on-site restaurants, which offered fresh seafood and Chesapeake-inspired dishes that made every meal memorable.

The location is another highlight—it’s only about an hour from Washington, D.C., yet it feels worlds away with its laid-back coastal atmosphere.

My favorite moment was sitting on the deck at sunset, sipping a drink and watching boats drift in and out of the marina—it was the perfect way to unwind.

For me, Rod 'N' Reel Resort is more than just a place to stay—it’s my favorite kind of getaway, where bayfront beauty, relaxation, and coastal adventure come together in one unforgettable experience.

Plan your Rod 'N' Reel getaway:

• Address: Rod 'N' Reel Resort, 4165 Mears Ave, Chesapeake Beach, MD 20732
• Drive Time from DC: ~1 hour southeast
• Cost: Rooms from ~$160/night

2. Wylder Hotel: Island Breezes & Bayfront Simplicity

We drove 1 hour 30 minutes southeast from Annapolis onto Tilghman Island at the tip of the Chesapeake Bay.

Wylder Hotel on Tilghman Island, Maryland, is one of my favorite Chesapeake Bay getaways.

I love that it has a laid-back, coastal vibe with a touch of boutique charm, making it an underrated retreat that feels both stylish and casual.

The hotel sits right on the water, and my favorite part was relaxing in an Adirondack chair by the bay, watching sailboats drift by as the sun set.

I found the rooms bright and cozy, with nautical-inspired décor, comfortable bedding, and balconies that made my stay feel fresh and inviting.

For couples, Wylder Hotel is one of the best romantic spots.

Families will also love it here, as the hotel offers bikes, kayaks, lawn games, and a pool that make it easy to enjoy the outdoors together.

My favorite highlight was dining on fresh local seafood—especially the oysters and crab—served right on the property, capturing the true flavor of the Chesapeake.

I especially loved the sense of community, with fire pits, hammocks, and open lawns that made it easy to unwind and feel at home.

The location is another plus—just a short drive from St. Michaels, yet far enough to feel like a peaceful island escape.

For me, Wylder Hotel is more than just a stay—it’s my favorite way to enjoy the Chesapeake Bay lifestyle, where relaxation, adventure, and coastal charm all come together in one unforgettable getaway.

Plan your Wylder Tilghman escape:

• Address: 21551 Chesapeake Acc, Tilghman Island, MD 21671
• Best Time to Visit: Late spring through early fall for warm nights and boat-watching
• Cost: Rooms from ~$200/night

3. Annapolis Waterfront Hotel: Nautical Views & Historic Walks

We drove 45 minutes east from Washington, D.C. into Annapolis, Maryland’s capital and a colonial seaport on the Chesapeake Bay.

Annapolis Waterfront Hotel, an Autograph Collection property, is one of my favorite coastal stays.

I love that it’s the only hotel right on the water in downtown Annapolis, giving it an unbeatable location with sweeping views of the harbor.

The atmosphere feels both refined and relaxed, making it an underrated choice for couples, families, or anyone wanting to soak in Chesapeake charm.

My favorite part was waking up to sailboats gliding across the bay from my private balcony—it was the best way to start the day.

I found the rooms modern and comfortable, with plush bedding, coastal-inspired décor, and plenty of natural light that made the stay feel fresh and inviting.

For couples, Annapolis Waterfront Hotel is a romantic escape, with waterfront dining, evening strolls along the docks, and easy access to charming downtown streets.

Families will also love the walkable location, close to shops, restaurants, and attractions like the U.S. Naval Academy and historic State House.

I especially enjoyed dining at Pusser’s Caribbean Grille, the on-site restaurant, where the food was delicious and the waterfront patio made every meal feel special.

The location is another highlight—you can step right outside and be in the heart of Annapolis, surrounded by history, sailing culture, and lively energy.

For me, Annapolis Waterfront Hotel is more than just a place to stay—it’s my favorite way to experience Maryland’s capital, where harbor views, coastal charm, and downtown convenience come together in one unforgettable getaway.

Plan your Annapolis Waterfront Hotel stay:

• Address: Annapolis Waterfront Hotel, 80 Compromise St, Annapolis, MD 21401
• Drive Time from DC: ~45 minutes east
• Cost: Rooms from ~$260/night

4. St. Michaels Harbour Inn, Marina and Spa - 1 hour 30 minutes from Baltimore

I drove 1 hour 15 minutes east from Annapolis into St. Michaels, a postcard-perfect harbor town on Maryland’s Eastern Shore. You can plan a visit to the Chesapeake Bay Maritime Museum, a stroll through Talbot Street’s boutiques and galleries, and a crab cake dinner overlooking the water.

St. Michaels Harbour Inn, Marina and Spa in Maryland is one of my favorite Chesapeake Bay escapes.

I love that it sits right on the harbor, giving it a perfect waterfront location where sailboats and sunsets create the most romantic backdrop.

The inn has a warm, welcoming atmosphere that feels both boutique and resort-like, making it an underrated choice for couples and families alike.

My favorite part was the private balcony off my room, where I could sip coffee in the morning and watch the boats drift in and out of the marina.

I found the accommodations spacious and comfortable, with plush bedding and nautical-inspired décor that fit perfectly with the harbor setting.

For couples, this inn is one of the best romantic getaways, offering a spa, waterfront dining, and quiet corners to relax together.

Families will also enjoy the pool, bike rentals, and easy walk into the charming town of St. Michaels with its shops and restaurants.

I especially loved the spa, where a relaxing massage made the weekend feel even more indulgent and restorative.

Dining at the on-site restaurant was another highlight, with fresh seafood and beautiful harbor views that made every meal feel special.

For me, St. Michaels Harbour Inn, Marina and Spa is more than just a stay—it’s my favorite kind of getaway, where waterfront beauty, comfort, and small-town charm all come together in one unforgettable experience.

Plan your Harbour Inn stay:

• Address: 101 N Harbour Rd, St. Michaels, MD 21663
• Drive Time from DC: ~1 hour 45 minutes east
• Cost: Rooms from ~$200/night

5. The Reynolds Tavern - 35 minutes

The Reynolds Tavern in Annapolis, Maryland, is one of my favorite historic inns in the USA.

I love that it dates back to 1747, making it one of the oldest taverns in America still in operation—an underrated treasure filled with character and history.

The atmosphere is warm and intimate, with colonial-style furnishings, cozy rooms, and a sense of stepping back in time while still enjoying modern comforts.

My favorite part was the afternoon tea service, which felt elegant and unique, complete with tiered trays of scones, sandwiches, and sweets.

I found the rooms quaint and comfortable, with antique décor, four-poster beds, and thoughtful touches that made the stay feel romantic and memorable.

For couples, The Reynolds Tavern is one of the best romantic getaways in Annapolis, with candlelit dinners, historic charm, and an unbeatable central location.

Families and history lovers will also enjoy the inn’s welcoming spirit and the chance to immerse themselves in colonial history right in the heart of downtown.

I especially loved dining in the cellar pub, which had a cozy atmosphere and hearty dishes that paired perfectly with local brews.

The location is another highlight—just steps from the Maryland State House, the waterfront, and Annapolis’s best shops and restaurants.

For me, The Reynolds Tavern is more than just an inn—it’s my favorite kind of getaway, where history, charm, and hospitality come together for an unforgettable Annapolis experience.

Plan your Reynolds Tavern retreat:

• Address: 7 Church Circle, Annapolis, MD 21401
• Drive Time from DC: ~45 minutes east
• Cost: Rooms from ~$195/night

6. Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

The Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge, Maryland, is one of my favorite bayside destinations.

I love that the resort sits on 342 acres along the Choptank River, giving it a grand yet peaceful atmosphere that feels both luxurious and inviting.

The property is a true hidden gem, offering everything from a full-service marina and golf course to multiple pools and a relaxing spa.

My favorite part was lounging by the infinity pool with sweeping water views—it felt like the best blend of resort luxury and coastal charm.

I found the rooms comfortable and bright, with private balconies, plush bedding, and nautical-inspired décor that made the stay feel refreshing and relaxing.

For couples, the resort is one of the best romantic escapes in Maryland, with sunset cruises, fine dining, and plenty of quiet corners to enjoy together.

Families will also love it here, thanks to the kid-friendly activities, Camp Hyatt, and wide-open spaces for biking, swimming, and exploring.

I especially enjoyed dining at Blue Point Provision Company, where fresh seafood and waterfront views made every meal memorable.

The resort’s spa was another highlight for me, offering indulgent treatments and peaceful spaces that made the weekend feel restorative.

For me, Hyatt Regency Chesapeake Bay is more than just a hotel—it’s my favorite kind of getaway, where nature, luxury, and family-friendly fun all come together in one unforgettable experience.

Plan your Hyatt Regency Chesapeake Bay getaway:

• Address: Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina, 100 Heron Blvd, Cambridge, MD 21613
• Drive Time from DC: ~1 hour 45 minutes southeast
• Cost: Rooms from ~$250/night

7. Wisp Resort

I drove 2 hours southeast from Pittsburgh to Wisp Resort in McHenry, Maryland. Nestled beside Deep Creek Lake, Wisp is Maryland’s only ski resort.

Wisp Resort in McHenry, Maryland, is one of my favorite mountain getaways, and it’s easily one of the best hidden gems for a weekend escape in the Mid-Atlantic.

I love that it sits right on Deep Creek Lake and offers year-round adventure, making it an underrated destination whether you’re visiting in summer or winter.

The resort feels like a true four-season playground, with skiing, snowboarding, and tubing in the colder months, and golf, zip-lining, and mountain coaster rides when it’s warm.

My favorite part was the ski-in, ski-out convenience during winter—it made the whole trip effortless and fun.

I found the accommodations comfortable and welcoming, with cozy décor and easy access to both the slopes and the lake.

For couples, Wisp Resort is one of the best adventurous getaways, offering scenic chairlift rides, lakefront sunsets, and plenty of ways to explore nature together.

Families will love the variety of activities, from kid-friendly ski programs to summer lake fun, making it one of the best all-around vacation spots in Maryland.

I especially enjoyed the mountaintop views, where you can see the rolling hills and sparkling waters of Deep Creek—it was my favorite highlight of the trip.

The on-site dining and nearby restaurants added to the convenience, letting me relax and enjoy après-ski meals without having to travel far.

For me, Wisp Resort is more than just a ski resort—it’s my favorite kind of year-round getaway, where adventure, relaxation, and natural beauty all come together in one unforgettable experience.

Plan your Wisp Resort getaway:

• Address: 296 Marsh Hill Rd, McHenry, MD 21541
• Drive Time from DC: ~3 hours west
• Cost: Rooms from ~$150/night

8. Ship Watch Inn

We drove 30 minutes south from Wilmington, Delaware, to Chesapeake City, a historic town perched along the C&D Canal. You can walk through the Victorian waterfront district, browse antique shops, and watch ships pass by from the canal-side promenade.

Ship Watch Inn in Chesapeake City, Maryland, is one of my favorite waterfront escapes.

I love that it’s a charming bed-and-breakfast right on the C&D Canal, giving it an intimate, cozy feel with unbeatable water views.

The inn feels wonderfully underrated, with just eight guest rooms, each offering a private balcony where I could watch ships quietly passing by.

My favorite part was relaxing on the deck with a cup of coffee in the morning, as the canal came to life with sailboats and barges—it felt both calming and fascinating.

I found the rooms comfortable and inviting, with plush bedding, whirlpool tubs, and thoughtful touches that made the stay feel special.

For couples, Ship Watch Inn is one of the best romantic retreats in Maryland, with a quiet setting, waterfront dining nearby, and sunsets that create the perfect atmosphere.

Families will also appreciate the welcoming vibe and the chance to explore Chesapeake City’s charming shops, restaurants, and historic streets just steps away.

I especially enjoyed the gourmet breakfast served each morning, which was delicious and made the experience feel even more personalized.

The location is another highlight—it’s tucked away in a quaint town yet close enough for easy access from Baltimore, Philadelphia, or Wilmington.

For me, Ship Watch Inn is more than just a place to stay—it’s my favorite kind of Chesapeake Bay getaway, where history, charm, and waterfront beauty come together for an unforgettable escape.

Plan your Ship Watch Inn stay:

• Address: 401 1st St, Chesapeake City, MD 21915
• Drive Time from DC: ~2 hours northeast
• Cost: Rooms from ~$180/night, including breakfast

9. Brampton Bed & Breakfast Inn: Chestertown’s Quiet Estate Elegance

I drove 1 hour 15 minutes northeast from Annapolis to Chestertown, a colonial port town on the Chester River. You can go on a walk along the brick-lined streets of the historic district, a visit to Washington College’s leafy campus, and a stop at the Garfield Center for the Arts before dining at a waterside tavern.

Brampton Bed & Breakfast Inn is one of my favorite romantic escapes on the Eastern Shore.

I love that the inn is set on 35 acres of gardens, meadows, and woodlands, giving it a peaceful and secluded atmosphere that feels wonderfully underrated.

The historic 1860s manor house is full of charm, and my favorite part was how each room and cottage has its own unique style, with fireplaces, canopy beds, and soaking tubs that made the stay feel so special.

I found the grounds absolutely beautiful, perfect for morning walks, afternoon picnics, or simply sitting under the trees with a good book.

For couples, Brampton is one of the best romantic retreats in Maryland, offering cozy cottages with private porches, in-room breakfasts, and serene settings made for connection.

Families will also love the larger suites and the open outdoor spaces that make it easy to relax and explore together.

My favorite highlight was the gourmet breakfast each morning—fresh, locally inspired, and delivered with so much care, it was the best way to start the day.

I especially loved the little details, like homemade cookies in the afternoon and thoughtful touches throughout the property, which made the inn feel warm and inviting.

The location is another plus, just minutes from the historic charm of Chestertown with its shops, galleries, and waterfront beauty.

For me, Brampton Bed & Breakfast Inn is more than just a stay—it’s my favorite kind of getaway, where history, romance, and natural beauty come together for an unforgettable Maryland escape.

Plan your Brampton getaway:

• Address: 25227 Chestertown Road, Chestertown, MD 21620
• Drive Time from DC: ~2 hours east
• Best Time to Visit: Spring through fall for full gardens and seasonal tranquility
• Cost: Rooms from ~$190–430/night, includes breakfast and tea

Hi, I'm Ema. Ready to plan your next weekend getaway? Let me help. I have 30 years of experience, over 400,000 social media followers, and my work as a travel expert has been mentioned on abc6 Morning Show, Best of the Web, USAToday, and many other outlets. When I'm not traveling around the USA, I live in Austin, TX with my husband and son. Click for more.

 

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