Book Holiday Homes in Royal Oak

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 Royal Oak

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
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Stevensville
The price is AU$440 per night from 7 Apr to 8 Apr
AU$440
includes taxes & fees
7 Apr - 8 Apr
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Located in North Beach, this vacation home is on the waterfront, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
Modern Waterfront House with Amazing views!
Save an average of 15% on thousands of hotels when you're signed in
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
When you stay at this vacation home in North Beach, you'll be on the beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water ...
Sweet Bamboo Beach Cottage
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
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2 out of 5
Annapolis
With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Grasonville
When you stay at this vacation home in Grasonville, you'll be within a 10-minute drive of Chesapeake Exploration Center and Queenstown Premium Outlets.
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
The Lazy Crab Beach House - Free beach passes

The Lazy Crab Beach House - Free beach passes

North Beach
A stay at this vacation home places you in the heart of North Beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Lazy Crab Beach House - Free beach passes
Don't see what you're looking for?
See all available properties in Royal Oak
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.

Royal Oak 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 Royal Oak vacation homes are the perfect way for you to wing it.

Holiday houses in Royal Oak 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 Royal Oak 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 Royal Oak adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Royal Oak 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 Royal Oak 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.

Royal Oak Holiday Homes essential information

Accommodation
361 Holiday Homes
Lowest Price
AU$159
Highest Price
AU$933
Popular accommodation
The Blue Crab Beach House - Free beach passes , ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Modern Waterfront House with Amazing views!, Sweet Bamboo Beach Cottage, Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Bay Breeze - Charming 3BR Waterfront Home on the Chester River, The Lazy Crab Beach House - Free beach passes

Top trending hotels in Royal Oak

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$450 per night from 21 Apr to 22 Apr
AU$450
includes taxes & fees
21 Apr - 22 Apr
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 27 Apr to 28 Apr
AU$226
includes taxes & fees
27 Apr - 28 Apr
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hyatt Place Kent Narrows & Marina
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$933 per night from 7 Apr to 8 Apr
AU$933
includes taxes & fees
7 Apr - 8 Apr
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Inn at Perry Cabin
Save an average of 15% on thousands of hotels when you're signed in
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 out of 5
3101 Main Street, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 9 Apr to 10 Apr
AU$159
includes taxes & fees
9 Apr - 10 Apr
A stay at Best Western Kent Narrows Inn places you in the heart of Grasonville, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island ...
Best Western Kent Narrows Inn
Don't see what you're looking for?
See all available properties in Royal Oak
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.