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

Directly Across from Gate One & Steps from the Waterfront

Directly Across from Gate One & Steps from the Waterfront

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 Gate One & Steps from the Waterfront
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
With a stay at this vacation home, you'll be centrally located in Deale, within a 10-minute drive of Upper Yough River and Franklin Point State Park.
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton
A stay at this vacation home places you in the heart of Crofton, a 1-minute drive from Walden Golf Club and 6 minutes from Bell Branch Big Dog Park.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Save an average of 15% on thousands of hotels when you're signed in
Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
With a stay at this vacation home in Shady Side, you'll be within a 5-minute drive of Shadyside Park and Captain Avery Museum.
Bay views with kayaks, bikes, fire pit, crabbing and more
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 U.S. Naval Academy and Sandy Point State Park.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Recently Renovated Annapolis Home - Conveniently Located

Recently Renovated Annapolis Home - Conveniently Located

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 People's Brewer Hill ...
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!

3 Story Stunner in Murray Hill <1 mile from USNA!

Annapolis
The price is AU$1,393 per night from 3 Dec to 4 Dec
AU$1,393
includes taxes & fees
3 Dec - 4 Dec
With a stay at this vacation home in Annapolis (Murray Hill), you'll be within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!

Your Annapolis Adventure Starts Here!!

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 10-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis
With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Chase Lloyd House.
Charming garden row home, easy 4 block walk to the heart of Annapolis.
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
630 Holiday Homes
Lowest Price
AU$342
Highest Price
AU$1,393
Popular accommodation
Directly Across from Gate One & Steps from the Waterfront , Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Bay views with kayaks, bikes, fire pit, crabbing and more, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Recently Renovated Annapolis Home - Conveniently Located, 3 Story Stunner in Murray Hill <1 mile from USNA!, Your Annapolis Adventure Starts Here!! , Charming garden row home, easy 4 block walk to the heart of Annapolis.

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
Fully refundableReserve now, pay when you stay
The price is AU$395 per night from 1 Dec to 2 Dec
AU$395
includes taxes & fees
1 Dec - 2 Dec
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
Kent Island Resort

Kent Island Resort

3.5 out of 5
500 Kent Manor Dr, Stevensville, MD
Fully refundable
The price is AU$342 per night from 1 Dec to 2 Dec
AU$342
includes taxes & fees
1 Dec - 2 Dec
Located in Stevensville, Kent Island Resort is on the waterfront, within a 15-minute drive of Chesapeake Bay Bridge and Queenstown Premium Outlets.
Kent Island Resort
Pool and Bay Views on wrap around deck in Kent Island

Pool and Bay Views on wrap around deck in Kent Island

Stevensville
With a stay at this vacation home in Stevensville, you'll be within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.
Pool and Bay Views on wrap around deck in Kent Island
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
The price is AU$391 per night from 25 Nov to 26 Nov
AU$391
includes taxes & fees
25 Nov - 26 Nov
Located in Stevensville, this vacation home is within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.
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.