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
Stay at this vacation home in Chestertown. Enjoy private pools, a garden, and patios.
Pet-Friendly Home on Chester River w/ Dock!
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
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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
Stay at this vacation home in Anne Arundel County. Enjoy free WiFi, private pools, and a sauna. Popular attractions Upper Yough River and 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
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
Stay at this vacation home in Shady Side. Enjoy a water park, patios, and cable/satellite TV service. Popular attractions Franklin Point State Park and Shadyside ...
Calloway Drive Retreat | House in Shady Side
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
Stay at this vacation home in St. Michaels. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions St. Michaels Museum and ...
Dollhouse in Central Historic St Michaels
Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

Annapolis
Book a stay at this beach vacation home in Annapolis. Enjoy a beach locale, a garden, and patios. Popular attractions Annapolis Golf Club and Bay Ridge Beach ...
Private Waterfront Woods | Dock, Kayaks, Views
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
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Chase Lloyd House and Hammond-Harwood ...
Charming garden row home, easy 4 block walk to the heart of Annapolis.
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
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions Navy-Marine Corps Memorial Stadium ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and bar

Centreville
Book a stay at this beach vacation home in Centreville. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Earle Landing and Hazel Miner Monument ...
Waterfront family resort Lodge with private pier, game room and bar
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
NZ$394
Highest Price
NZ$507
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Calloway Drive Retreat | House in Shady Side, Dollhouse in Central Historic St Michaels, Private Waterfront Woods | Dock, Kayaks, Views, Charming garden row home, easy 4 block walk to the heart of Annapolis., Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Waterfront family resort Lodge with private pier, game room and bar

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 NZ$507 per night from 5 Jan to 6 Jan
NZ$507
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 4-star spa hotel in Stevensville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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 NZ$394 per night from 24 Dec to 25 Dec
NZ$394
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this golf hotel in Stevensville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
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
Stay at this vacation home in Stevensville. Enjoy free WiFi, private pools, and a garden. Popular attractions Matapeake State Park and Bay Ridge Beach are located ...
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 NZ$453 per night from 7 Jan to 8 Jan
NZ$453
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this vacation home in Stevensville. Enjoy free WiFi, a garden, and patios. Popular attraction Matapeake State Park is located nearby.
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.