start a vacation rental business

If you happen to live in Maryland, you know how beautiful it can be in the summer. The long coastline and the picturesque small towns make it a perfect summer gateway for anyone looking for peace. If you want to spend your summers on the Atlantic Ocean, get to know Maryland’s coolest towns to buy a vacation home. Once you settle in one of these towns, you will be able to enjoy and discover either the seaside or the countryside of the Old Line State. Packed with a rich history, all of these places have much to offer to their residents and visitors alike. Let us review some of the most prominent small towns in Maryland and help you decide on your vacation investment.

Berlin was once voted America’s Coolest Small Town

Berlin is one of Maryland’s most picturesque towns, located in Worcester County. Even though it shares the name with Germany’s capital, residents say its origin is quite different. There was once an old tavern called Burleigh Inn, and the whole town got called Berlin as a variation to the old tavern’s name.

This little town is famous for being featured in the movie “Runaway Bride” starring Julia Roberts. The town center is renowned for traditional Victorian houses and is very popular among visitors and vacationers. Also, it is a popular destination for anyone who enjoys fishing and hunting. There are many places available for rent, so buying a vacation home in this town could potentially be an opportunity to start a vacation rental business. Visit Berlin and let its characteristic and charming historic downtown speak for itself. 

Chesapeake City is a town filled with history

If you are looking to find Maryland’s coolest towns to buy a vacation home, Chesapeake City should be high on your list. This town is rich in history and 19th-century architecture, making it very attractive to tourists and visitors. Most old buildings are now restaurants, small hotels, and inns and represent excellent investment opportunities in a vacation rental. If you choose Chesapeake City as your permanent summer address, you will be able to enjoy the Chesapeake & Delaware Canal and discover the wonders of the countryside.

Also, you can visit the Canal Museum, learn about the canal’s rich history, and even see a replica of the famous lighthouse. Enjoy the Bay in all its splendor, try a great variety of fresh seafood and make your summers in Maryland memorable.

Frederick represents a perfect mix of historic and modern

If you live in Baltimore or Washington DC, you should consider Frederick an ideal town to buy a vacation home. Or even a permanent new residence. As summer approaches, relocating to Frederick seems like a great idea. It is a perfect summer vacation gateway, with town streets full of shops, restaurants, galleries, and rich history all around. The nature is breathtaking as the town sits near the mountains but also close to the sea. Even though the city is famous for its historical flare, you can enjoy the modern life aspects of it.

So, if you are relocating some of your furniture and belongings to your newly purchased vacation house, or you have realized you have to remodel a bit, this town has got you covered. If you need a storage unit to place your items until the house is ready, you can use the Frederick-based facilities. One of the best perks of this town is that you will be able to commute to major cities in the area but have everything you need within walking distance when in town.

Annapolis was once the nation’s capital and today a lively tourist destination

If you want to enjoy warm temperatures throughout spring and summer, Annapolis can give you that experience. Vacationing here will provide you with a chance to immerse yourself in American history but also enjoy the outdoors as much as you can. You can take hikes, enjoy some delicious seafood and take in all the wonders of 17th century downtown.

The town is well known for its military college and attracts top military students to Maryland. It is also home to some of the best museums in the state, a vibrant art community, and many summer festivals and events. If you have considered ever seeking work in the tourism industry, choosing to purchase a vacation home in a tourist destination such as Annapolis can be an excellent decision for your future.

Ocean City might be the beach town of your dreams

Ocean City might be an ideal place for anyone looking to spend their summer near the ocean, on sandy beaches but not far from home. It is one of Maryland’s coolest towns to buy a vacation home, especially if you are in the market for a more luxury option. According to moving specialists from Zippy Shell DMV, who service both Maryland and Virginia areas, more and more couples and families come to Ocean City to soak up the sun and the breathtaking scenery.

Here you can expect an eclectic season full of fun and activities. Off-season, there is less hustle, and you can enjoy the views on the Atlantic Ocean in peace and quiet. When in town, don’t miss heading to the waterpark or having a nice seafood dinner in one of many restaurants. 

Experience small-town Maryland while settling here for the summer

Besides all the Maryland’s coolest towns to buy a vacation home we have mentioned, there are still some great places to consider. The state is famous for its small towns along the coastline. People from all over, including Virginia and DC, are opting to settle here, at least for the summer. Good food, green outdoors, the ocean, and rich history come as solid contenders for the best summer experience.

Towns like Thurmont in Frederick County or Crisfield in Somerset could be your next summer gateway full of wonders to explore. Whatever Maryland destination you choose for escaping the busy life in a large city, you will find something for yourself and your family. Although tourist destinations, most of the towns offer affordable living, and there are still possibilities to find work.   

By Anurag Rathod

Anurag Rathod is an Editor of, who is passionate for app-based startup solutions and on-demand business ideas. He believes in spreading tech trends. He is an avid reader and loves thinking out of the box to promote new technologies.