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

Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
With a stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Kings Town Park and Historical Society of Kent County Maryland.
Pet-Friendly Home on Chester River w/ Dock!
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis
With a stay at this vacation home in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Save an average of 15% on thousands of hotels when you're signed in
Brand New Spacious Luxury Home

Brand New Spacious Luxury Home

Annapolis
With a stay at this vacation home in Annapolis, you'll be within a 5-minute drive of U.S. Naval Academy and Spa Creek.
Brand New Spacious Luxury Home
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!
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 15-minute walk of Waterman’s Museum and Rock Hall Harbor.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Freshly renovated 3-story home 1 block from USNA!

Freshly renovated 3-story home 1 block from USNA!

Annapolis
The price is AU$1,041 per night from 12 Jan to 13 Jan
AU$1,041
includes taxes & fees
12 Jan - 13 Jan
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and John Smith House.
Freshly renovated 3-story home 1 block from USNA!
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
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
628 Holiday Homes
Lowest Price
AU$359
Highest Price
AU$1,041
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Brand New Spacious Luxury Home, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Waterfront w/private pier, pool, Hot Tub, kayaks and in town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Freshly renovated 3-story home 1 block from USNA!, Dollhouse in Central Historic St Michaels

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$398 per night from 12 Jan to 13 Jan
AU$398
includes taxes & fees
12 Jan - 13 Jan
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$359 per night from 12 Jan to 13 Jan
AU$359
includes taxes & fees
12 Jan - 13 Jan
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
When you stay at this vacation home in Stevensville, you'll be within a 10-minute drive of Matapeake State Park and Romancoke Wharf County Park.
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$360 per night from 12 Jan to 13 Jan
AU$360
includes taxes & fees
12 Jan - 13 Jan
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.