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!
15 Best Weekend Getaways in Maryland You Must Try
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!
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!
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.
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.
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!
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!
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.
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.
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!
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 .
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.
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!
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.
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.