Discovering the charm of Maryland’s small towns is a perfect way for solo female travelers to enjoy a fun, active, and memorable holiday filled with local experiences and things to do. These quaint destinations are known for their rich character, welcoming communities, and unique attractions, making them ideal for holiday accommodation at cozy vacation rentals or short-term rentals that feel like a home away from home. Whether you’re planning a weekend getaway with friends or an extended stay exploring Maryland’s hidden gems, these small towns provide a fantastic backdrop for your next adventure.
1. St. Michaels: A Historic Harbour Town with Endless Activities
Nestled along the Chesapeake Bay, St. Michaels is a captivating destination featuring historic charm, vibrant local culture, and stunning waterfront views. This quintessential Maryland town offers a variety of holiday rentals that blend historic character with modern comfort, perfect for a fun and flirty getaway. From cozy cottages by the water to luxurious bed and breakfasts, you can find the ideal accommodation in St. Michaels through trusted sites like Search and Stay.
When staying in St. Michaels, you’re only minutes away from fantastic activities such as sailing, kayaking, and even exploring the historic Morgan State House Museum. Foodies will love the local seafood restaurants serving up fresh oysters and Chesapeake Bay blue crabs, perfect for enjoying a relaxed holiday with friends. For those seeking outdoor fun, consider renting a boat or joining a fishing tour to experience the bay’s vibrant marine life. Don’t miss visiting the historic St. Michaels Harbour Inn & Spa for a touch of luxury after a day of active adventures.
For a perfect day out, explore the local shops and art galleries downtown before heading to the Chesapeake Bay Maritime Museum. Their engaging exhibits provide insights into the rich maritime history of the area, ideal for active explorers. And if you’re interested in local experiences, check out [Maryland’s Eastern Shore](https://www.visitmaryland.org/listing/activities/attractions-museums/maritime-museum-st-michaels/2495) for things to do in the area.
2. Berlin: A Small Town with Big Charm and Big Local Experiences
While it might be small, Berlin boasts a lively arts scene, historic streets, and an abundance of fun activities that make it a fantastic destination for a holiday stay. Known for its quirky shops, antique boutiques, and impressive street murals, Berlin offers a perfect blend of cultural exploration and outdoor recreation. Accommodation options in Berlin range from charming bed and breakfast accommodations to modern vacation rentals—perfect for a group of friends looking to explore Maryland’s local experiences.
Get your adrenaline pumping by trail biking or hiking through the nearby Assateague Island National Seashore, famous for its wild horses and pristine beaches. Rent a bike and enjoy a scenic ride along the coast, or take a boat tour to see the island’s natural beauty from the water. The town also hosts seasonal festivals and farmers markets where you can sample fresh local produce and handmade goods—experiences that truly enrich your holiday.
For those interested in local history, visit the Calvin B. Taylor House Museum to learn about Berlin’s past or participate in a historic walking tour. And, of course, a trip to Berlin wouldn’t be complete without experiencing its vibrant nightlife scene, which includes cozy pubs and live music venues. To find an ideal place to stay in Berlin, you can use Search and Stay.
3. Leonardtown: The Heart of Maryland’s Southern Charm
For a relaxed holiday full of scenic beauty and local experiences, Leonardtown in Southern Maryland offers a charming small-town atmosphere that is ideal for active travelers seeking a mix of leisure and adventure. The town’s welcoming community and picturesque streets make it an inviting place to stay in vacation rentals that boast a cozy, small-town vibe.
Active visitors can enjoy exploring the nearby St. Mary’s River on paddleboards or kayaks, exploring the birder-friendly Patuxent River State Park, or taking part in fun fishing activities. For a more laid-back experience, stroll through the historic district, visiting boutique shops and art galleries, before indulging in local cuisine at farm-to-table restaurants.
History buffs can explore the historic St. Mary’s City, which offers engaging exhibits on Maryland’s colonial past, perfect for a few educational hours amid active sightseeing. Additionally, Leonardtown hosts several annual events and festivals celebrating local culture, music, and art—activities that enhance your holiday experience.
Find local accommodation options via Search and Stay and plan your active holiday with insight into the best places to stay in Leonardtown.
4. Oxford: A Charming Water-Oriented Town with Unique Things to Do
Oxford is a serene small town offering the perfect setting for a fun and flirty holiday with friends. Known for its historic waterfront houses, sailing culture, and friendly community, Oxford provides a relaxing yet active environment ideal for outdoor adventures and local experiences.
Enjoy renting a vacation home with stunning water views to enhance your stay in this peaceful town. During your visit, indulge in activities like sailing lessons, windsurfing, or paddleboarding across the Chesapeake Bay. For those interested in exploring local history, tours of the centuries-old Oxford Museum will immerse you in the area’s past.
Make sure to visit the local farm markets and enjoy fresh seafood along the waterfront. If you’re up for a bit of exploring, consider taking a boat trip to nearby islands, or hire a guide to discover hidden coves and beaches. For a scenic day out, the nearby Tred Avon River provides perfect spots for relaxation and active water activities.
To find the best accommodation in Oxford for your active holiday, visit Search and Stay.
5. Chestertown: A Historic Town with a Vibrant Local Scene
The historic Chestertown combines colonial architecture, a lively arts scene, and outdoor pursuits that make it a prime destination for holiday rentals and active exploration. This friendly town offers an array of things to do, from exploring historic sites to engaging in outdoor activities along the Chester River.
You can rent a cozy cottage or a spacious home, providing the perfect base for your adventures. Active travelers will enjoy kayaking and paddleboarding on the river, cycling along scenic routes, or participating in local festivals such as the Chestertown Tea Party. If you love history, take guided tours of historic homes and museums that showcase Maryland’s colonial past.
For a dash of local flavor, visit the Chestertown Farmers’ Market or enjoy live music at community events. Whether you’re booking a holiday rental or a short-term stay, the town’s welcoming ambience makes it easy to unwind and embrace the local character.
Secure your ideal place to stay in Chestertown through Search and Stay and prepare for a holiday filled with active pursuits and enriching local experiences.
Whether it’s exploring historic streets, engaging in active water sports, or sampling local flavors, Maryland’s small towns offer an ideal mix of character and fun for the adventurous, active holidaymaker. Use this guide to choose where to stay, find your perfect vacation rental, and plan your trip around the many things to do. Remember, the best holiday accommodations in Maryland can be found easily through Search and Stay, making your planning seamless and enjoyable.