Holiday rentals in Overlea

The Fisherman's Lodge at the 1858 Monkton Hotel

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. An electric bike store, tube rental and great cafe are all in the same building.

Hotel perks suite near Baltimore and top hospitals

Whether you're a medical professional, remote worker, or traveler, this private garden-level suite is a blend of hotel perks and home comfort — conveniently near the highway, plazas, a bus stop, and much more. ✔ Work & unwind –sit-stand desk, fast WiFi + smart TV ✔ Fully stocked – Coffee, snacks, fridge & microwave ✔ Comfy rest – Queen bed & blackout curtains ✔ Ample storage – Drawers & walk-in closet ✔ Self-care ready – Fitness gear, robe & beauty products ✔ Private entrance -No shared spaces

Stunning 1BR Apt. in Historic Row Home w/ Parking

Just steps from Baltimore’s Inner Harbor, Fells Point, Little Italy, and John’s Hopkins Hospital, this fully equipped one bedroom apartment has everything you need! This modern and contemporary unit inside one of Baltimore’s historic row homes (built 1850) features tall ceilings and beautiful floor to ceiling windows. Apartment includes a full kitchen, full bathroom, one bedroom with office space, living room with HD TV and sofa bed, and a washer/dryer in unit. A bike is also available for use!

Butchershill- Clean, Fireplace, King Bed, Parking!

My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

Waterfront Romantic Studio

Unwind at our private studio getaway-featuring an updated kitchen & bathroom, and cozy sleeping area. Separate entrance for complete privacy. Step out onto the shared deck and take in stunning water views, perfect for your morning coffee or a relaxing evening drink enjoy the waterfront vibe. Make memories around the fire pit or explore nearby state parks with scenic hiking trails and beaches. Whether you’re here for a show, a convention, or just some sightseeing, only 20 minutes from Baltimore.

RetroLux Guest Suite 20 min to Downtown Baltimore

Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

Basement Guest Suite & Retreat - Waltherson

Enjoy historic Waltherson! A 15-minute drive to downtown Baltimore. Within walking distance of Walther Gardens, the neighborhood nursery, gift shop, and famous snowball stand. Fully furnished basement suite with queen cabinet bed, living room, bathroom, cable TV, Netflix, wifi, basic dishes/utensils, HVAC, and laundry room. The area has a mini fridge, microwave, coffee pot, kuerig, tea kettle, and bottled water. There is no cook top/stove or kitchen sink. Keyless entry. No smoking in unit.

Studio Apartment at historic Walnut Grove

Apartment in the wing of the historic Walnut Grove farmhouse with its own central heating and cooling and spa tub. Our farmette has 10 free range hens outside your window, and pets. Beautiful sunsets, bald eagles, osprey, and water fowl viewed from the dock across the street. Close to Baltimore and 5 miles from 95. Local dining, shopping, parks, and golf course, tennis court at the school. No smoking , vaping or pot allowed inside or outside.

Tree house resort spa with sauna

Escape to a Secluded Sanctuary in the Woods. Located just 6 minutes from Baltimore City, this home is part of a unique collection of 3 villas, each nestled on 3.5 acres of lush, wooded land, complete with private driveways. Relax in your own private guest suite with its own entrance, surrounded by nature’s serenity. This peaceful retreat is designed to make you feel like you’re far away from the everyday, offering the perfect couples’ escape.

Bright and Cozy 2nd floor apt

My place is within walking distance of restaurants and family-friendly activities, within minutes of White Marsh Mall, easy freeway access for going to an Orioles/Ravens game, and the Inner Harbor or just hike a neighborhood trail. You’ll love my place because of Connivence to everything, in a quiet friendly neighborhood and private entrance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Artful Retreat + Your Home Away from Home

Curated 2BR urban retreat in Baltimore’s Hamilton-Lauraville. Artful home features dedicated workspace, furnished backyard with fire pit & private dining space—perfect for remote workers, traveling nurses/professors/military. Eclectic decor, 1930s craftsman charm w/modern amenities. Ideal for extended stays, weekend getaways, or intimate gatherings. Pet-friendly. Free parking. STR-0003281