Weekend Getaways in Maryland
After a whirlwind city week, 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.
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 during my four weeks of road tripping on the East Coast that I think you’ll love for your next weekend adventure.
1. Rod 'N' Reel Resort in Chesapeake Beach
I thought that Rod 'N' Reel Resort in Chesapeake Beach, Maryland was one of the best weekend getaways in Maryland. Why? I love that it combines the charm of a seaside retreat with modern amenities, making it an underrated destination for both relaxation and adventure.
I drove one 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 at 1936 Bar & Grill.
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.
My room for two days was 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 since it’s only about an hour from Washington, D.C., yet it feels worlds away with its laid-back coastal atmosphere. We enjoyed visiting CalvertHealth Farmers Market on Tuesday afternoon (April through November).
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. It's one of my favorite waterfront escapes along the Chesapeake Bay.
To book, check availability or prices for the 3-star Rod 'N' Reel Resort.
My favorite highlight was a 60-minute Reflexology treatment at the spa and then sitting on the deck at sunset watching boats drift in and out of the marina. It was the perfect way to unwind.
2. Wylder Hotel on Tilghman Island
Wylder Hotel on Tilghman Island, Maryland, is one of my favorite Chesapeake Bay weekend getaways. Why? 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.
We drove 1 hour 30 minutes southeast from Annapolis onto Tilghman Island at the tip of the Chesapeake Bay.
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.
Our room for four days was bright and cozy, with nautical-inspired décor, comfortable bedding, and balconies that made my stay feel fresh and inviting.
You can trust that this is a truly unique hotel experience because it's on Condé Nast Traveler's “Top Hotels in New York State & the Mid-Atlantic” — Wylder was ranked #11 by readers in that region.
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.
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 my favorite way to enjoy the Chesapeake Bay lifestyle, where relaxation, adventure, and coastal charm all come together in one unforgettable getaway.
To book, check availability or prices for the 3-star Wylder Hotel.
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.
3. Annapolis Waterfront Hotel
Annapolis Waterfront Hotel 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.
We drove 45 minutes east from Washington, D.C. into Annapolis, Maryland’s capital and a colonial seaport on the Chesapeake Bay.
The atmosphere at 3-star Annapolis Waterfront Hotel 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.
The location is another highlight because you can step right outside and be in the heart of Annapolis, surrounded by history, sailing culture, and lively energy. You can enjoy tours of the U.S. Naval Academy and historic sites like the Maryland State House and William Paca House & Garden. Enjoy the water at Ego Alley, or explore nature at Quiet Waters Park and Sandy Point State Park.
For me, Annapolis Waterfront Hotel is my favorite way to experience Maryland’s capital, where harbor views, coastal charm, and downtown convenience come together in one unforgettable getaway.
To book, check availability or prices for the 3-star Annapolis Waterfront Hotel.
My personal highlight was waking up to a beautiful view in the morning.
4. St. Michaels Harbour Inn, Marina and Spa
St. Michaels Harbour Inn, Marina and Spa in Maryland is one of my favorite Chesapeake Bay escapes that completely won me over. I love that it sits right on the harbor, giving it a perfect waterfront location where sailboats and sunsets create the most romantic backdrop.
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.
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 for two days, 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 in Maryland, 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.
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.
To book, check availability or prices for the 3-star St. Michaels Harbour Inn, Marina and Spa.
My highlight was spending a few hours at the spa, where a relaxing massage made the weekend feel even more indulgent and restorative.
5. The Reynolds Tavern
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.
Our suite for two days was very 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, MD, 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.
To book, check availability or prices for The Reynolds Tavern.
My favorite highlight was the afternoon tea service, which felt elegant and unique, complete with tiered trays of scones, sandwiches, and sweets.
6. Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore
I thought that that The Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge, Maryland was one of the best weekend getaways in Maryland. Why? 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.
Our room for two days was comfortable and bright, with a private balcony, 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. All in all, I loved how nature, luxury, and family-friendly fun all come together here in one unforgettable experience.
To book, check availability or prices for the 4-star Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina.
My favorite highlight was lounging by the infinity pool with sweeping water views—it felt like the best blend of resort luxury and coastal charm.
7. Wisp 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.
We drove two hours southeast from Pittsburgh to Wisp Resort in McHenry, Maryland. Nestled beside Deep Creek Lake, Wisp is Maryland’s only ski resort.
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 our accommodations for two days 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.
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.
To book, check availability or prices for the 3-star Wisp Resort.
My personal highlight were the mountaintop views, where you can see the rolling hills and sparkling waters of Deep Creek—it was my favorite highlight of the trip.
8. Ship Watch Inn
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.
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.
The inn feels wonderfully underrated, with just eight guest rooms, each offering a private balcony where I could watch ships quietly passing by.
Our room for two days came 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.
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 because it’s tucked away in a quaint town yet close enough for easy access from Baltimore, Philadelphia, or Wilmington.
Ship Watch Inn is my favorite kind of Chesapeake Bay getaway, where history, charm, and waterfront beauty come together for an unforgettable escape.
To book, check availability or prices for Ship Watch Inn.
My favorite highlight 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.
9. Brampton 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.
I thought that Brampton Bed & Breakfast Inn was one of the best romantic getaways on the Eastern Shore, also perfect for a quick honeymoon. Why? 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. Our room for two days had a fireplace, canopy bed, and a soaking tub 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, a true local gem.
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.
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.
To book, check availability or prices for Brampton Bed & Breakfast Inn.
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.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
5. If you are planning to visit more than three national parks in the next 12 months, buy the America the Beautiful Pass.
