Entire Home/Apt (a private rental)
Shared Home/Apt (the owner is present)

Maryland Vacation Rentals (14 properties)

View By: List Photos

Need help booking? Call us at (925) 965-2621


Last Minute Booking Rates Discount


Last Minute Booking Rates Discount

I was so lucky to find this place last minute when my previous home cancelled on our group of girls due to 'maintenance issues', and to be honest - this was the much better option! Paula was fantastic to work with, very accommodating. The view can't be beat and the house was roomy enough to host us 8 ladies, plus plenty of dishes, cookware and linens to spare. The girly decorations were perfect for the bride to be who we were celebrating for the trip. Also, great location in terms of getting around Kent Island - a quick drive to the Cascia Winery, Blackwater Distilling, The Jetty (all visited and highly recommended!) and Food Lion for picking up things to cook. Thanks, Paula!
Sasha Kalcheff
This is a great place to relax! Big waterfront yard, dock, feels private. We sunbathed on the deck, jumped off the dock and played volleyball in the yard. The guys had fun fishing. Once we had enough sun and swimming for the day we cooled off in the many comfortable rooms in the house. The lower level is great with Ping-Pong, foosball and big flat screens. The house is at the end of the point, so you can go for a run without traffic and then enjoy the beautiful sunset over the water. A very comfortable vacation spot with everything you could want to get away have fun and relax!
TJ Harvey
per night

Vacation Rentals in Maryland

Maryland’s nickname of “America in miniature” succinctly sums up the small Mid-Atlantic state. Booking a Maryland vacation rental give you access to such diverse cities as metropolitan Baltimore located just north of U.S. capital Washington, D.C. to the sleepy coastal communities around Chesapeake Bay and the Eastern Shore.

The western tip of the state is located within the Appalachian Mountains and has many cabin rentals that are perfect for vacationers looking for a quiet mountain getaway, or wanting to hike the Appalachian Trail. Add your name to the long list of people that have climbed Annapolis Rock, or catch a Baltimore Ravens or Orioles game and cheer on the local professional teams.

Many dishes can be found on local menus that feature local seafood, including raw oysters, steamed mussels and blue crab. A popular dish is a “burger” made of soft shell crab served on a bun with lettuce, mustard and tomato. Crab cakes are also abundantly found in the region, particularly around the lower part of the Maryland coast. The best type is perhaps the jumbo lump crab cakes served at Baltimore’s Lexington Market. Book a vacation home and spend some time exploring this tiny region that has some pretty big flavors.

Book one of the Oakland vacation homes in Maryland Western during October to be a part of Autumn Glory Festival. Ocean City is another happening tourist destination of Maryland with loads of shopping centers, high class hotels, resorts, restaurants, easily accessible from Ocean City condo vacation rentals.

The city of McHenry, located on the northern most shore of Deep Creek Lake, is known for its superb accommodations. Rent one of the cabin rentals in McHenry to access the well-known Wisp Ski Resort and Golf Club, situated right on the outskirts of the city. To experience an exotic beach holiday, reserve any of the oceanfront Maryland vacation rentals.

Sit in the balcony of your Maryland beach house and enjoy a lazy afternoon. From the sleepy fishing villages of St. Michaels and Chrisfield, to the museums in Baltimore, to 'America's sailing capital' - Annapolis, you will find plenty of Maryland condo rentals wherever you go within the most affordable price ranges.

Search for more vacation homes in nearby states:

Virginia Vacation Rentals
District of Columbia Vacation Rentals
Pennsylvania Vacation Rentals
Delaware Vacation Rentals
Read More

Popular Vacation Rentals in Maryland

Properties About Which You Are Inquiring

Contact the Owner
* *
Are these Dates Flexible?YesNo
Adults Children
Please send me the owner's phone number: By Email   By Text

See AlwaysOnVacation Terms of Use for more information.