Book Holiday Homes in Stevensville

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Featured Holiday Homes in Stevensville

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.
Opens in a new windowDirectly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach
Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
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 Chesapeake Bay.
Opens in a new windowTurning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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Historic Row Home 1 Block from Gate 1 at USNA!

Historic Row Home 1 Block from Gate 1 at USNA!

Annapolis
The price is AU$1,153 per night from 20 Nov to 21 Nov
AU$1,153
20 Nov - 21 Nov
includes taxes & fees
Located in Annapolis (Historic District), this vacation home is within a 5-minute walk of U.S. Naval Academy and Annapolis City Dock.
Opens in a new windowHistoric Row Home 1 Block from Gate 1 at USNA!
Charming Historic Annapolis Home With Two Off-street Parking Places!

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis
This vacation home is in the heart of Annapolis, within a 10-minute walk of John Smith House and U.S. Naval Academy.
Opens in a new windowCharming Historic Annapolis Home With Two Off-street Parking Places!
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.
Opens in a new windowSpacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena
Located in Pasadena, this vacation home is on the waterfront, within a 10-minute drive of Fort Smallwood Park and Compass Pointe Golf Courses.
Opens in a new windowFirepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Deale
Located in Deale, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowMillion Dollar View of the Chesapeake Bay
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
The price is AU$475 per night from 20 Nov to 21 Nov
AU$475
20 Nov - 21 Nov
includes taxes & fees
With a stay at this vacation home in Arnold, you'll be within a 15-minute drive of U.S. Naval Academy and Severna Park Golf Center.
Opens in a new windowLarge 2 bedroom house with private parking in a nice neighborhood
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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
748 Holiday Homes
Lowest Price
AU$351
Highest Price
AU$1,153
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Cozy Crab- Your Charming Haven in Lovely North Beach!, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Historic Row Home 1 Block from Gate 1 at USNA!, Charming Historic Annapolis Home With Two Off-street Parking Places!, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !, Million Dollar View of the Chesapeake Bay, Large 2 bedroom house with private parking in a nice neighborhood

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$351 per night from 7 Dec to 8 Dec
AU$351
7 Dec - 8 Dec
includes taxes & fees
With a stay at The Inn at Chesapeake Bay Beach Club in Stevensville, you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowThe Inn at Chesapeake Bay Beach Club
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville
Located in Stevensville, this vacation home is by the sea, within a 10-minute drive of Matapeake State Park and Chesapeake Bay.
Opens in a new windowWoodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
Stevensville
Located in Stevensville, this houseboat is on the beach, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowFloating 2 bed 2 bath condo stunning views of the bay
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Kent Island Resort

Kent Island Resort

3.5 out of 5
500 Kent Manor Dr, Stevensville, MD
Fully refundableReserve now, pay when you stay
The price is AU$361 per night from 1 Dec to 2 Dec
AU$361
1 Dec - 2 Dec
includes taxes & fees
Located in Stevensville, Kent Island Resort is on the waterfront, within a 15-minute drive of Chesapeake Bay Bridge and Queenstown Premium Outlets.
Opens in a new windowKent Island Resort
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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.

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^Subject to availability and chosen travel dates.