Book Holiday Homes in Stevensville

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Stevensville

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Dollhouse in Central Historic St Michaels
Save an average of 15% on thousands of hotels when you're signed in
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of Annapolis City Dock and U.S. Naval Academy.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Annapolis
With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Annapolis City Dock.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of Annapolis City Dock and U.S. Naval Academy.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis City Dock.
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute walk of Annapolis City Dock and U.S. Naval Academy.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Adorable waterside cottage with pool Beach community

Adorable waterside cottage with pool Beach community

Edgewater
Located in Edgewater, this vacation home is on the waterfront, a 3-minute drive from Sand Point Marsh and 9 minutes from Triton Beach.
Adorable waterside cottage with pool Beach community
Don't see what you're looking for?
See all available properties in Stevensville
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stevensville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Stevensville vacation homes are the perfect way for you to wing it.

Holiday houses in Stevensville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Stevensville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Stevensville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Stevensville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Stevensville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Stevensville Holiday Homes essential information

Accommodation
793 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Blue Crab Beach House - Free beach passes , Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Dollhouse in Central Historic St Michaels, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium, Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, Adorable waterside cottage with pool Beach community

Top trending hotels in Stevensville

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road, Stevensville, MD
With a stay at The Inn at Chesapeake Bay Beach Club in Stevensville, you'll be within a 5-minute drive of Paul Reed Smith Guitars and Matapeake State Park.
The Inn at Chesapeake Bay Beach Club
Island Life!  Kent Island Waterfront with Pool-Bring your boat!

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville
Located in Stevensville, this guesthouse is on the waterfront, within a 10-minute drive of Paul Reed Smith Guitars and Island Dog Park.
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Matapeake State Park and 6 minutes from Paul Reed Smith Guitars.
Circa 1700 Chesapeake Colonial home on the National Register.
Save an average of 15% on thousands of hotels when you're signed in
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
Located in Stevensville, this vacation home is within a 15-minute drive of Romancoke Wharf County Park and Matapeake State Park.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Don't see what you're looking for?
See all available properties in Stevensville
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.