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13 Top-Rated Weekend Getaways in Maryland

Written by Alison Abbott and Barbara Radcliffe Rogers Updated Jul 13, 2022 We may earn a commission from affiliate links ( )

Life's frenetic pace can sometimes make a long-distance vacation difficult. For those living in Maryland and the surrounding states, there are plenty of places to visit nearby to get away from it all.

Tourists from out of state will find a real slice of Americana here as well. This East Coast state has a varied landscape, from beaches to mountains, and is filled with some of the oldest cities in the country, perfect for weekend escapes.

No matter what type of escape you enjoy, finding it in Maryland won't be difficult. Pack your bags and plan your trip with our list of the top weekend getaways in Maryland.

1. Baltimore

2. historic annapolis, 3. ocean city, 4. a waterside weekend in st. michaels, 5. frederick, 6. deep creek lake, 7. assateague island, 8. walking or cycling along the c&o canal, 9. tilghman island, maryland, 10. spend a weekend antique shopping in hagerstown, 11. st. mary's city, 12. chesapeake city, 13. kent island, map of weekend getaways in maryland.

Baltimore's Inner Harbor at dusk

Baltimore is a bustling waterfront city. Whether you are craving culture or just want to get a taste of the famous Maryland seafood specialties, Baltimore has a little something for everyone in a weekend getaway. Family-friendly attractions like touring the USS Constellation or seeing oddities at Ripley's Believe it or Not offer plenty of fun.

The waterfront is a destination all on its own. You can enjoy world-class dining and shopping or head to one of the many museums here, like the B&O Railroad Museum or the Reginald F. Lewis Museum of Maryland African American History & Culture .

Art lovers should take in the Baltimore Museum of Art , with the largest collection of works by Henri Matisse in the world. Don't forget to indulge in some of the famous seafood while you are in town. Sports fans should check the schedule and catch an Orioles game at Camden Yards in the spring or summer.

If you are a fan of repurposed buildings, book a stay at The Inn at Henderson's Wharf. This popular waterfront spot is in the Fells Point neighborhood, with cobbled streets and many shops and restaurants a short walk away.

  • Read More: Top-Rated Attractions in Baltimore, Maryland

Thurgood Marshall Monument in front of the Maryland State House

While it may be famous for its military college, Annapolis, Maryland offers much more than the United States Naval Academy. It's a historical and cultural mecca. Did you know that Annapolis was the temporary capital of the United States from 1783-1784? The historical significance here is strong, which makes it a great weekend getaway for history buffs and families.

A visit here is not complete without taking a stroll on what is known as "Historic Annapolis" to enjoy the restaurants, shopping, and beautiful architecture. After a busy day of walking through American history, take a break at the serene Quiet Waters Park , where you can stroll or rest along the South River. Before leaving the city, take an hour or two to tour the United State Naval Academy and the Maryland State House .

There are plenty of places to stay while you visit Annapolis, but a historic bed-and-breakfast seems appropriate with all that history. From the Flag House Inn , you will be within walking distance of everything downtown. The chef and hosts offer excellent hospitality.

  • Read More: Top-Rated Attractions & Things to Do in Annapolis

Ocean City beach and pier

If your perfect weekend getaway includes sand and fun in the sun, Ocean City is a great place to visit. This beach town, nestled on the Atlantic Ocean and home to one of the best beaches in Maryland , is the summer playground for many Maryland, Virginia, and D.C. families.

This bustling town hosts over eight million visitors annually. Off-season, you can expect a quieter experience, and fall is a great time to soak up the breathtaking views of the Atlantic while enjoying great deals on hotels without the crowds of tourists.

Although the beach is the biggest draw to Ocean City, there are plenty of other things to do to keep you busy. Surfing and parasailing are available for the adventurous, and who doesn't love a sunset cruise?

If you are looking for less adventure, walk the two-and-a-half-mile boardwalk, where you will enjoy many unique shops and seaside treats, like salt-water taffy or some of Maryland's famous seafood. If you love the water but not the sand, head to the Jolly Roger Water Park .

Aerial view of  St. Michaels, Maryland

Enjoy the pleasures of the Chesapeake Bay, from sailing to seafood, in the picturesque waterside town of St. Michaels. On the bay side of the Eastern Shore, St. Michaels combines the maritime flavor of a historic harbor with luxury lodging and dining.

Get a sense of the region's history and culture at the Chesapeake Bay Maritime Museum, centered around the 1879 Hooper Strait Lighthouse and including a working boatyard. Take to the water on a cruise; you have a wide choice, from a traditional skipjack to an air-conditioned launch to a sailing cruise.

For a more active weekend, you can kayak on the beautiful Miles River, or take a sailing lesson.

You'll find maritime-themed gifts at the museum shop or at the range of smart shops and boutiques scattered among the mid-1600s homes near the harbor.

Cherry blossoms over a covered bridge

Nestled at the foot of the mountains and known as the gateway to western Maryland, Frederick has a rich history, which shines brightly in its 40-block historic district, filled with shops, galleries, and restaurants. It's easy to see why this is a popular weekend getaway for those living in Baltimore and Washington D.C.

For a history lesson of Frederick, take a tour of Monocacy National Battlefield and stop by the visitor center, where you will learn about the 1864 battle of Monocacy Junction, which took place here. Afterwards, visit one of Frederick's many historic attractions, like the National Museum of Civil War Medicine or the Schifferstadt Architectural Museum.

Kids will love the Rose Hill Manor Park and Children's Museum, which gives them a glimpse into early American life. Another fun family-friendly activity is a vintage train ride on the Walkersville Southern Railroad. Top off your visit with a stay at the Homewood Suites by Hilton, with all-suite rooms, free parking, Wi-Fi, and breakfast.

Fall colors at Deep Creek Lake

If you are looking for a weekend getaway at the lake, Deep Creek Lake is a great choice. Located in Western Maryland, Deep Creek Lake is a busy summertime destination for city dwellers looking to escape the concrete jungle.

Water sports, spas, restaurants, shops, and more make this a perfect getaway for families. Kids will love the Discovery Center at Deep Creek State Park , where they will learn about the area's wildlife and history with interactive exhibits and an on-site aviary. For those seeking adventure, try the Monkey Business Aerial Adventure Park for climbing and ziplining.

Wild horses on Assateague Island

Only nine miles south of Ocean City , Maryland, but a world away, is the Assateague Island National Seashore. This national park is home to wild horses, which roam along the beaches. This unspoiled island offers breathtaking views and a chance to get up close and personal with nature in all its glory. You can rest and recharge on the beach, take a swim in the ocean, or take advantage of one of their ranger-guided tours.

Biking is a great way to see the island. There are a few trails to choose from that will take you from the marsh to the sandy beaches. Because the island is part of the National Seashore, the closest accommodations will be in Ocean City, Maryland.

The Chesapeake and Ohio Canal

A project strongly advocated by George Washington, who was at the time commander of Fort Cumberland, the Chesapeake and Ohio Canal reaches from Washington, DC, to Cumberland and was built between 1828 and 1850.

It borders the Potomac River through central Maryland, a corridor for recreation and a historic link that ties together the two cities of Cumberland and Hagerstown. Either of these makes a good base for excursions on foot, by bicycle, or by canoe or kayak on the Potomac River, which borders the canal.

The Chesapeake and Ohio Canal National Historic Park is a rare linear park, preserving the canal route, maintaining its towpath and the historic buildings. A surprising number of the canal's features are intact, including locks, tunnels, and 10 of the 11 aqueducts that carried the canal over streams and rivers. Perhaps the most impressive of the remains is the 3,118-foot-long Paw Paw Tunnel, which you can walk through.

Canal access points are well marked on the free national park map, along with campsites, Potomac boat launches, picnic sites, and points of interest. You can rent bicycles, kayaks, and canoes at several points.

A convenient base for exploring the C&O Canal is at the Fairfield Inn & Suites Cumberland , a budget-friendly hotel with a pool and free breakfasts.

Official site: https://www.canaltrust.org

Tilghman Island and Chesapeake Bay

For a laid-back, relaxing waterfront getaway, try Tilghman Island. This old-fashioned fishing village located in Talbot County is a perfect respite from the daily grind. Situated between the Chesapeake Bay and Choptank River, the island can be accessed by car or boat. Just be aware that the drawbridge to Tilghman Island is reported to be one of the busiest in the US, so plan accordingly.

On the island, you won't find any chain stores, just a laid-back way of life, which will let you rest and recharge for the weekend. While you are here, check out the Tilghman Watermen's Museum , which celebrates the rich history of the island's maritime culture and features historical artifacts and local artists. You will also want to get your fill of fresh seafood, for which the island is well known.

Complete your visit with a stay at Lowes Wharf Marina Inn , between St. Michaels and Tilghman Island, with waterfront guest rooms, a restaurant, marina, private beach, and beautiful sunsets.

Antiques in a small shop

At least 20 shops and antiques co-ops cluster in the area immediately around Hagerstown, a lively small city in central Maryland.

In the downtown area, you'll find Washington County Trading Company, The Wandering Geranium, Junkworks Antiques, and two thrift shops.

At Coinopwarehouse on E. Franklin Street, browse through a huge collection of jukeboxes, pinball machines, vintage signs, video games, and coin-operated antiques. Olde Time Treasures on Pennsylvania Avenue is an indoor flea market.

South of the center on Rte. 40-W, you'll find Memory Lane Antiques & Collectibles, with 10,000 square feet of consigned goods.

Farther south on Rt. 40 is a cluster of three shops: Antique Crossroads and Beaver Creek Antique Market are both multi-dealer malls, while A&J Antiques is a smaller shop with more select items.

Historic building in St. Mary's City

A former colonial town and the first capital of Maryland, St. Mary's City is a weekend getaway guaranteed to take the tourist back in time. This state-run historic area features a colonial settlement, living history recreation, and museums. History buffs and families will enjoy the live exhibits.

Step into life in the 1600s with a first-hand glimpse at farming during the time period, Civil War reenactments, and interactive colonial-era games.

Be sure to explore the town center. Visitors can tour an authentic mercantile and see what early colonists would have bought 400 years ago. Before you leave, walk down to the waterfront and tour the historic ships in the port, a favorite with visitors. It's not just about the colonists; you can also learn about the native Yaocomaco with a visit to the Woodland Indian Hamlet .

Visitors can stay in Lexington City, a quick five miles away, at the Comfort Inn & Suites Lexington Park . This reliable brand offers free Wi-Fi, parking, and a hot breakfast and is convenient to several restaurants nearby.

Chesapeake City

Close to the water and filled with many attractions, another great choice for a weekend getaway is Chesapeake City. The only town in Maryland that is on a working commercial canal, Chesapeake City is filled with 19th-century grandeur. Stop by the Canal Museum , where you can learn about the busy waterway and also see a replica of a lighthouse that kept ships safe over the centuries.

Even though Chesapeake City is the third largest city in Virginia, it has a small-town charm. Visitors will love the abundance of independent stores, restaurants, and charming bed-and-breakfasts.

Get the full experience and sweeping views of this town on a sunset cruise with the Chesapeake City Ferry, or a bike ride down the C&D Canal Recreational Trail , which links the C&D Canal to Delaware Bay.

Kent Island

For couples wanting a romantic escape or families wanting a laid-back weekend getaway, Kent Island will not disappoint. This island, which is the largest in the Chesapeake Bay, has plenty to keep you busy without the traffic and congestion of the mainland.

Families will love the Chesapeake Exploration Center , which gives an excellent history of the area. Sunset is a great time to take a walk on their scenic path and get a view of the local birds like the osprey. Oftentimes they are busy feeding. You can also explore Terrapin Beach Park .

When you are on the island, you will want to stay at The Inn at Chesapeake Bay Beach Club and Spa . This amazing property will have you relaxed and recharged in no time. They feature farm-to-table food from local farmers and amenities like a full-service salon, spa, and fitness center. The luxuriously appointed guest rooms are the perfect place to unwind, and when the sun goes down, head to the fire pit to lounge and relax under a blanket of stars.

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waterfall in Mallows state park with fall foliage

15 Best Weekend Getaways in Maryland You Must Try

January 21, 2023 //  by  Southern Trippers

Are you looking for a list of the best weekend getaways in Maryland? If so, we have you covered with the best places to visit!

Although Maryland is one of Americans smallest states, it is jammed pack with so many exciting weekend getaways! Maryland is known for the Chesapeake Bay , epic waterways and byways, and it’s capital city Baltimore!

Head to Ocean City for a beach weekend, or head to Annapolis for a historical weekend, or just drive along the byways for fall foliage. For those looking for romantic weekend getaways in Maryland, why not visit one of the spa hotels or go wine tasting!

From short day trips to extended weekend trips, to even a weeklong cruise along the Chesapeake bay the options for weekend getaways in Maryland are endless!

The chesapeake bay is a highlight of weekend getaways in Maryland.

Ocean City Maryland Weekend Getaway 

Ocean City is one of the most well known places to visit in Maryland for the weekend! This resort town sits on an island between the Atlantic Ocean and the Isle of Wight Bay. Best known for its boardwalk with an amusement park. But, is also filled with shopping, restaurants, and entertainment there is something for everyone to do here!

Although it is know for having one of the best beaches . There are also golf courses, breweries and distilleries like Seacrets to explore. Next, go shopping, visit the theme park making it the perfect family weekend getaway in Maryland! Take the family to the boardwalk for the day. Here you can taste the famous crab cakes or the boardwalk fries and more. Don’t forget about going on rides in the amusement park!

There are over 200 restaurants in Ocean city to explore. Head to the Ocean City Center for the arts, catch a summer concert, or just relax on the 10 miles of beachfront. Families can camp at one of the 600 sites in Frontier town just 5 miles from Ocean City. The campground is complete with lazy river, waterslides, putt putt golf and more! 

an ariel view of one of the best weekend getaways in Maryland - ocean city with the beach, boardwalk and citry

Washington DC Weekend Getaway

Washington Dc is a great option for those looking at weekend trips from Baltimore! Baltimore airport is just an hour from DC, and is often a lower cost alternative if flying into the area as it is serviced by low cost carriers. Plus, as the capital of the US it has tons of things to do and see .

Most of the museums ( Smithsonian ) are free in DC ! We think this makes for a great option for those looking for weekend getaways in Maryland on a budget! Head to the capitol for a free tour, sign up for White house tour, or stroll along the National Wall to see the monuments. There is so much to see and do, and best of all it’s almost all free! 

Washington DC is a fairly walkable city, and a lot of the most famous sites are pretty close together or you can take the Metro around the city making it easy to get around.

We have put together the perfect 3-day itinerary perfect for a long weekend getaway! From sights, dining, hotels and more we have you covered!

the view of the capitol building and the mall in washington dc

Princess Royale Oceanfront Resort 

For those looking for one of the best staycations in Maryland, head to the Princess Royale Oceanfront Resort. Located right on the Atlantic Ocean, this hotel is the perfect place to unwind. The hotel features a gorgeous indoor olympic sized pool that is housed inside a 4 story glass atrium! Complete with a tiki hut bar, restaurants, an oceanfront sundeck, and a prime location!

Many of the rooms feature ocean view balconies! Sit back and enjoy the ocean breeze while enjoying a beverage of your choice. Plus, the kitchenettes are perfect for keeping beach snacks. Just a few minutes walk from the Ocean Plaza Mall where you can shop and dine, or just steps from the beach! Furthermore, the hotel features free parking for those driving into town on weekend trips from Baltimore.  We vote this as one of the inexpensive romantic getaways in Maryland!

Inn At Perry Cabin

The Inn at Perry Cabin, is one of the places to stay for romantic weekend getaways in Maryland. For those not looking for a beachfront vacation, but instead looking to stay on Maryland’s Eastern Shore, this colonial mansion is a full service hotel with breathtaking views of the Chesapeake Bay.

The property features an outdoor pool with plenty of lounge chairs, a fitness center where you can take yoga classes. Or take a walk through the grounds with flower gardens filled with hydrangeas and a greenhouse, and chairs overlooking the Bay. Once in your room, you will be greeted by neutral colors with an upscale feel, and gorgeous bathrooms both perfect for a romantic couples weekend.

In addition to being one of the top spa resorts in Maryland, the spa at Perry Cabin is known for its luxurious treatments made with aromatics grown on the grounds. There is even a couples treatment room, in addition the spa offers an outdoor infinity pool, steam room and more!

Head to the waterfront restaurant for breakfast. Lunch and dinner, or sip a cocktail by the fireplace at Pursers Pub. Or you can walk the 10 minutes into St. Michael’s town center. 

enjoy the couples massage room with homemade botanicals in the Spa at the Inn at Perry Cabin

134 Prince – Annapolis

Looking for spa resorts in Maryland? Well, the 134 Prince is for you complete with spa bath rooms! Located in Annapolis, this 5 star resort is perfect for Maryland weekend getaways! Just a mile from the harbor, this hotel features lush gardens, private parking, a relaxing family room, marble bathrooms, all housed in a colonial manor home. 

Head downstairs and relax in front of the charming fireplace in the hotel’s living room. Lastly, walk outdoors through the gardens for fresh air, or relax in your very own spa room. With bright neutrals and amazing marble bathrooms complete with soaking tubs, and glass showers perfect for unwinding after a day of exploring Annapolis.

Head to Ego Alley at the marina where you can stroll along the docks looks at yachts or walk along the brick streets for delicious restaurants and shops.

the marina area with restaurants and shops at Ego alley in Annapolois

Havre de Grace

One of your weekend trips in Maryland must include Harve de Grace, or HDG as it is affectionately known to Marylanders. The town sits on the Susquehanna River and the  Chesapeake Bay, and was named after the French town of Le Harve. This charming historic town is one of the must visits in the area. 

Stroll along the waterfront on one of the many scenic trails like the Harve de Grace Promenade. Next, head into town to visit museums like the Grace decoy museum known for creating decoy ducks. For those looking to shop- antiquing is big here! OR visit the lighthouse.

Seafood lovers you are lucky as the restaurants here serve up fresh caught seafood and the town hosts a variety of events from farmers markets, to music festivals, and fundraisers. 

What’s more for water lovers, you can sail around the Chesapeake Harbor, or head to the golf course at Bulle Rock. 

This is truly one of the cutest small towns in Maryland!

the lighthouse at HDC

Fall Foliage Road Trip

If you are visiting Maryland in fall, a full foliage road trip is a great idea! Starting in September  the season runs through the end of November where visitors will be rewarded with golden and red hues of leaves.  And perfect for those looking for cheap weekend getaways in Maryland, as it costs nothing to explore the outdoors! Maryland is known for its scenic byways and we will suggest all the best places to go!

Garrett County hosts an Autumn Glory. This 5 day festival celebrates the beauty of fall with floats, concerts, arts and crafts and more! This is the perfect place to start your fall foliage driving tour and you can head south, or north on pre planned routes. 

Next, we suggest the Chesapeake and Ohio canal scenic byway known by its nickname the Grand Old Ditch. Travel along the 200 mile route where you will see 19th century engineering in the form of old locks as you follow along the river and breathtaking vistas with fall leaves. 

For those short on time, or just want a day trip, head to Deep Creek Lake. You will be rewarded with autumn hues, overlooking a gorgeous lake in western Maryland. Finally, in just 30 minutes you can drive along the lake, or take a longer drive exploring Civil War sights, or rent a kayak or canoe and paddle along the shoreline for views!

a hiker checking out the fall foliage in Maryland

Wild Ponies And Camping At Assateague State Park

The wild horses of Assateague state park are well known outside of Maryland. The horses are actually split into two herds one of the Maryland side and one of the Virginia side. For the Maryland side they are part of the National Seashore . The entrance to the national park is $25 per vehicle or $15 per person. And for those looking to camp, you can camp on the barrier island !

The wild herd of 78 is managed by the National Park Service and you must stay at least 40 feet from the herds, and never touch, pet or feed the wild horses. The horses are wild, and can be seen frolicking along the beach , or in the barrier island Marshes or further inland drinking water at one of the freshwater ponds. Folklore says it was a shipwreck that brought the horses to the island or that farmers let horses roam free to avoid paying taxes!

Visitors can hike along the trails, along the beach, or kayak in the water offshore for sightings of the wild horses, along with birds, and marine life. 

the wild horses is the perfect place for a weekend getaway in Maryland

Mallows Bay

Mallows Bay is a Potomac River National Marine Sanctuary and is a must visit for any outdoor or nature enthusiast. Just 30 miles from DC, this is a great option to visit in Southern Maryland! For history lovers, there are remnants of over 200 WWI wooden ships known as the “ghost fleet” sunk under the water.

In addition, there are Civil War sites and Native American history to explore. And for water lovers you can kayak or canoe through the wooden ship graveyard. 

We think this is one of the options for a weekend trips in Maryland! The best time of the year to visit is between May and September and then during low-tide as the ships can best be seen.

They have now become a natural water habitats for a variety of marine and wildlife and ecology that captivates visitors.  You can visit daily from 5:30 am to sunset. This is the perfect short weekend trip if you are already in the DC area.

Come visit the ghost ships underwater at mallows bay Sanctuary is one of the inexpensive weekend getaways in Maryland

Swallow Falls State Park

If you are in Oakland, head to Swallow Falls State Park just 9 miles north of Oakland. It is home to some of the most scenic viewpoints. Set along the Youghiogheny River, view the park’s borders, rock gorges and more. Culminating at Muddy Creek Falls’s 53 foot waterfall! Plus the hike is only about a mile.

The park is open daily from 8 am to sunset, and offers 65 campsites with bathhouses. As well as 3 full hook up service for campers or motorhomes and 3 cabins that can be rented! For those looking to camp, this makes for a very inexpensive weekend getaway in Maryland!

Visitors can fish for rainbow trout and more, go whitewater rafting down the river with its rugged scenery, or hike one of the 5.5 mile Heritage trails for those looking for a longer loop. The entry fee is $3 for Maryland residents or $5 for visitors. 

Also in the area is Deep Creek Lake. This outdoor lover’s paradise is perfect to visit year round. From fishing in the summer, to fall foliage, to winter where you can ski nearby!

the 53 foot water fall with fall leaves at Marrow State Park

Maryland Wine Trail Romantic Weekend Getaway in Maryland

For those looking for romantic weekend getaways in Maryland, what could be more romantic than hitting the Maryland wine trail? Head to the Piedmont Plateau, Frederick and Chesapeake wine trail or the Mason-dixon wine trail just to name a few of the 9 wine trails in Maryland.

Winemaking in Maryland dates back to 1648 with grapes planted on the St. Marry River. Today, the climate allows for over 36 different grape varieties to grow creating amazing and unique blends.

On the Chesapeake Trail you can visit 14 breathtaking wineries around the peninsula. Cozy up in waterfront tasting rooms and explore historic towns! This sounds like one the best weekend getaways in Maryland for those looking to taste wines.

On the Frederick Wine trail ( the oldest wine trail) there are 8 different vineyards to visit in the rolling hills. And include some of the oldest wineries in the state. Try a tasting flight while enjoying the outdoors and light bites to eat. Make sure to check out the best things to do in Frederick while you are here!

Carroll County is home to the Maryland Wine Festival that has taken place in September for the last 38 years. Wineries, breweries and distilleries come together for this festival. Held on the Farm Museums ground, enjoy the spirits, restaurants from around the area, live music, crafts and shops and more! For an extra special weekend book the Explore Village pass .

a wine tasting overlooking the water in Maryland perfect for a romatntic weekend getaway in Maryland

Kent Island

Kent Island is located off the west coast of Queen Anne’s County, separated from the mainland by the Kent Narrows channel. If you are a history buff, this town was founded in 1631, and is the 3rd oldest settlement in the country, after Jamestown and Plymouth!

This island is built from its steamboat and trading port beginnings to a bustling water town. There are big name hotels, historic inns and a ton of seafood restaurants. Explore the marinas, lighthouse, or head to one of the nature parks.

Also on the island is the 500 acer The Wildfowl Trust of North America , with a wetland sanctuary. Visitors can rent kayaks and paddle through the wetlands from May to November.

the chesapeake bay is on display here  on kent island

Cruise up the Chesapeake Bay

If you are looking for unique mini vacations in Maryland, why not cruise up the Chesapeake Bay. Believe it or not, you can take a 7 day cruise up the Chesapeake Bay stopping at historic ports and gorgeous cities along the way. In fact, the cruise ship was built right here in Maryland. We think this is one of the best Maryland getaways, for those looking for an all inclusive vacation option.

The round-trip cruise departs and returns to Baltimore stopping in Yorktown/Williamsburg , Tangier Island, Crisfield , Cambridge , Oxford , St Michaels and Annapolis. These are not your large cruise ships, but smaller river cruises. The ship carries about 100 guests, with meals prepared from local flavors of the area.

Each of the staterooms feature outward facing cabins with large picture windows or balconies. There is daily entertainment on the ships, as well as tours offered at each port! So board the ship then sit back and relax as your travel along the Chesapeake Bay without having to do any of the planning or driving!

a cheasapeak cruise boat with the city in background

Baltimore Getaway

We have an entire article dedicated to a weekend in Baltimore for those looking for a full itinerary. But we could not have a weekend getaway list without having Baltimore on it! Many visit for the weekend because of the dreamy views throughout the city and tons of activities and places to explore.

Most of the attractions are inside the Inner Harbor area making this an easy city to navigate. Why not take a harbor cruise, visit the aquarium, and the science center. Next, is the more historic Federal Hill area and the Mount Vernon area is filled with museums like the Walters Art Museum, The Famous Peabody and Enoch Pratt Free Library, and the Maryland Historical society. The things to do in Baltimore are endless.

For those looking to shop and eat, head to Hampden. “The Avenue” us where you can check out the best boutique shops, bars, and  restaurants  in Baltimore.

baltimore at sunset overlooking the harbor.

Annapolis a historic Weekend Getaway in Maryland

As the capital of Maryland, Annapolis has been the location of many historical events. While many know it as the home of the US Naval Academy, the town offers much more than that. But we highly recommend signing up for a tour!

The Treaty of Paris was signed there, ending the Revolutionary War. Plus, the four founding fathers from Maryland that signed the Declaration of Independence all had homes here so the historical sites are plentiful! We have picked out the best things to do in Annapolis .

The history, attractions, and mouthwatering food is what makes Annapolis one of the best weekend getaways in Maryland! This is a seafood lovers dream, as this town is known for the freshest seafood around.

Whether you are a foodie looking for new dishes to try, a history buff looking to dive into the coastal past, or just a traveler wanting to have fun in a new city, you will find something to fit your needs in this beautiful city.

annapolis is a historic town

VacationIdea

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25 Best Weekend Getaways in Maryland for Couples

Last Updated By VI on April 18, 2024 in Weekend Getaways From D.C. & Day Trips

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

Wylder hotel, tilghman island - 1 hour 50 min, annapolis waterfront hotel, st. michaels harbour inn, marina and spa - 1 hour 30 minutes from baltimore.

  • See the Complete List

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

More ideas: Beaches in Maryland , Day trips , Luxury Weekend Getaways

Wylder Hotel, Tilghman Island - 1 hour 50 min

Wylder Hotel on Tilghman Island , 21551 Chesapeake House Dr, Tilghman, MD 21671, 410-886-2121

Annapolis Waterfront Hotel

Annapolis Waterfront Hotel , 80 Compromise Street, Annapolis, MD 21401, 410-268-7555

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

101 N. Harbor Rd, St. Michaels, Maryland 21663, 410-745-9001

The Reynolds Tavern - 35 minutes

The Reynolds Tavern - 35 minutes

7 Church Circle, Annapolis, Maryland 21401, 410-295-9555

Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

Hyatt Regency Chesapeake Bay - 1 hour 30 minutes from Baltimore

100 Heron Blvd. at Route 50, Cambridge, Maryland, 21613, 410-901-1234

Wisp Resort

Wisp Resort

Browse fall vacation getaways in Maryland .

Gaylord National Resort

Gaylord National Resort

201 Waterfront Street, National Harbor, Maryland 20745, 301-965-4000

The Columbia Inn at Peralynna

The Columbia Inn at Peralynna

10605 State Route 108, Columbia, Maryland 21044, 410-715-4600

Great Oak Manor, Maryland

Great Oak Manor, Maryland

10568 Cliff Rd, Chestertown, Maryland 21620, 410-778-5943

Sandaway Suites & Beach

Sandaway Suites & Beach

103 West Strand Road, Oxford, Maryland 21654, 888-726-3292

Lake Pointe Inn

Lake Pointe Inn

Lake Pointe Inn, 174 Lake Pointe Drive, McHenry, MD 21541, 301-804-6221

Laurel Grove Inn on the South River

Laurel Grove Inn on the South River

2881 South Haven Rd, Annapolis, MD 21401, 443-370-2394

Gramercy Mansion, Maryland

Gramercy Mansion, Maryland

1400 Greenspring Valley Road, Stevenson, Maryland 21153, 410-486-2405

Inn at Herrington Harbour - 1 hour 15 minutes

Inn at Herrington Harbour - 1 hour 15 minutes

North Carolina Vacations SC Weekend Getaways Weekend Getaways From Atlanta Connecticut Rhode Island Weekend Getaways

Rocky Gap Casino and Resort

Rocky Gap Casino and Resort

16701 Lakeview Road, Flinstone, MD 21530, 301-784-8400

Haley Farm Spa and Retreat Center

Haley Farm Spa and Retreat Center

16766 Garrett Highway, Oakland, MD 21550, 301-387-2471

Inn at Perry Cabin, St. Michaels

Inn at Perry Cabin, St. Michaels

308 Watkins Lane, St. Michaels, MD 21663, 888-805-8885

Hotel Brexton

Hotel Brexton

868 Park Avenue, Baltimore, MD 21201, 443-478-2100

1840s Carrollton Inn

1840s Carrollton Inn

50 Albemarle Street, Baltimore, MD 21202, 410-385-1840

Savage River Lodge

Savage River Lodge

1600 Mt Aetna Rd, Frostburg, MD 21532, Phone: 301-689-3200

Live! Casino and Hotel, Hanover

Live! Casino and Hotel, Hanover

Live! Casino and Hotel, 7002 Arundel Mills, Circle 7777, Hanover , MD 21076, 855-563-5483

The Inn at Chesapeake Bay Beach Club, Kent Island

The Inn at Chesapeake Bay Beach Club, Kent Island

A very popular venue for destination weddings, the The Inn at Chesapeake Bay Beach Club on Kent Island is also a perfect place to spend a romantic weekend getaway. The beautiful surroundings and the views over Chesapeake Bay encourage couples to relax and unwind – perhaps you can start your weekend by enjoying a pampering Couples Retreat at the on-site spa. The Inn has one of the original farm-to-fork eateries which showcase fresh farm produce (from their own gardens) and exceptional local fish and seafood. The Inn at Chesapeake Bay Beach Club, 180 Pier One Road, Stevensville, MD 21666, 410 604 5900

The Lodges at Sunset Village, Mc Henry

The Lodges at Sunset Village, Mc Henry

The Lodges at Sunset Village, 23900 Garrett Highway, McHenry, MD 21541, 301-387-2227

Annapolis

After all that history, you can stroll down to Ego Alley in historic Downtown to see some of the most stunning and exotic yachts. If you would like to get out on the water yourself, you can go on a cruise with Woodwind or Watermark Cruises or take sailing lessons at the Annapolis Sailing School. At Annapolis Canoe and Kayak you can rent everything you need for a day of fun out on the water. Foodies should not miss an Original Annapolis Seafood Crawl. Read more: 25 Best Romantic Restaurants in Annapolis, Maryland .--->

Bethesda started out as a tiny crossroads village and has blossomed into a bustling and modern city with a thriving arts scene and many attractions for visitors.