Room service is nice, but have you ever spent the night in a treehouse? How about on a houseboat? Or a caboose?
This region is full of surprising places to sleep, from round houses with true 360-degree views to floating houseboats to, yes, sleeping in a caboose.
We gathered up some of the most eclectic accommodations within a four-hour drive of Baltimore’s Inner Harbor.
Pack your beach towel, your sunscreen, your bug spray, and your sense of adventure; and don’t forget to reserve way in advance. Turns out, the more outlandish the sleeping arrangements, the more popular they are.
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Round House, Greenbackville, Virginia
Starts at $255 per night

When one of my oldest friends asked me if I wanted to work remotely for a few days at a place on the water, I was game. When she forwarded me photos of the Round House of Greenbackville, I couldn’t wait. It did not disappoint.
I arrived and parked in front of a spherical home, feeling like a reporter for Architectural Digest. After ascending the serpentine outdoor staircase, then the indoor spiral one, I arrived at the house’s biggest selling point – a living room that could double as an observation deck. In front of us was a cove, beautifully landscaped, and a deck that circled the house. All of the furniture was round. We settled in, worked productively during the day, and spent our evenings at Chincoteague’s wildlife refuge among the horses and the waves. The Captain’s Cove development comes with access to golf, a pool and pickleball, but we were there to work.
There are challenges to staying in a sphere — the paucity of outlets comes to mind — but they are more than made up for with the 360-degree views. We’re already planning another “vacation-from-work” work trip next year.
Tree house village, Bittinger, Maryland
Starts at $325 per night
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Luxury treehouse may sound like an oxymoron, but these accommodations level up in more ways than one. Ella’s Enchanted treehouses hug the Savage River State Forest, providing both endless hiking opportunities and a climate about 10 degrees cooler than Baltimore’s.
Kids love treehouses, but Ella’s is just as much fun without them. Deep Creek Lake and Wisp Ski Resort are nearby, as well as several farm-to-table restaurants and cheese shops. You’re not far from Green Ridge State Forest, the largest contiguous block of public forest in the state, and definitely one of the prettiest. What Western Maryland lacks in beaches, it makes up for with all of this shade. Bonus (or maybe not): If you plan ahead you can book enough treehouses for your own large family gathering.
Yacht home, numerous locations, Maryland
Starts at $607 per night, various prices, two-night minimum
A year ago, married Banner reporters Tim Prudente and Christina Tkacik spent a couple of nights in FLOHOM, a yacht hotel on Baltimore’s Inner Harbor. They enjoyed the view from the 53-foot houseboat, as well as the thoughtful touches, like fancy soaps and fluffy robes. Tim did note that, at times, the air was pungent. Now, FLOHOM has expanded to some less pungent locations.
The company offers the houseboat experience at several other locations around Baltimore, including Canton, as well as a berth on the Magothy River in Pasadena and one in Annapolis. Attending a convention at National Harbor? Forgo the conference hotel and book a couple of nights on a floating houseboat. All the other attendees will wish they had the same bright idea. FLOHOM does require a two-night minimum, which will give you a chance to figure out if yacht life is for you.
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Lighthouse, Cove Point, Maryland
Starting at $5,592 for seven nights

If someone close to you is a lighthouse aficionado, this is the place to take them. The property sleeps eight people and includes a 40-foot-high brick light tower as well as a private beach. The lighthouse was established in 1828, making it the fifth-oldest on the Chesapeake Bay. The Calvert Marine Museum owns this one, and the funds for rentals go to maintain the property and run programs. Also included on the site are the century-old fog bell building and the Coast Guard radio transmitter, according to the property listing.
Other lighthouse bed-and-breakfasts have closed because of the difficulty in getting guests out into the middle of a waterway. At Cove Point, though, you’re on the mainland, so you can order a pizza from Lusby and have it delivered. There’s something to be said for modern conveniences while enjoying a view of the Chesapeake that looks much like it did two hundred years ago.
Caboose car, Ronks, Pennsylvania
Starting at $179
Many a train enthusiast has delighted at a night in one of the cars at the Red Caboose Motel in the heart of Amish Country in Lancaster County. The property, now called Paradise Station, offers 38 cabooses, but also a baggage car, mail car, farmhouse and a conductor’s quarters. To continue the theme, visit the Strasburg Railroad for historic steam train rides with different themes for adults and children.(Whiskey on the Rails, anyone? Or a Wine and Cheese Train Ride?)
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Lancaster County was a favorite destination when my kids were younger, but I’d go back today without them to enjoy more adult pursuits. Lancaster Central Market has terrific selections of fresh meat, cheese, and produce. The city has a growing brewing industry, with more than a dozen local spots to try some new beers.
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