Book Holiday Homes in Royal Oak

Start date: Check-in selected.
To Date
End date: Check-out

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 Cozy Crab- Your Charming Haven in Lovely North Beach!

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

North Beach MD
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!
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Opens in a new windowCozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Opens in a new windowNEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Save an average of 15% on thousands of hotels when you're signed in
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels MD
With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and Muskrat Park.
Opens in a new windowDowntown St. Michaels | Walk to Shops, Restaurants and Nightlife
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick MD
With a stay at this vacation home in Prince Frederick, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new window2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick MD
Located in Prince Frederick, this vacation home is near the beach, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowKick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Beautiful 2-bedroom water view house in Annapolis

Beautiful 2-bedroom water view house in Annapolis

Annapolis MD
With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowBeautiful 2-bedroom water view house in Annapolis
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Easton MD
With a stay at this vacation home in Easton, you'll be on the beach, and 6.6 mi (10.7 km) from Saint Michaels Village and 7.3 mi (11.7 km) from St. Michaels ...
Opens in a new windowWoodwind Manor on the Tred Avon minutes to St Michaels and Easton.
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
335 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$343
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space., Beautiful 2-bedroom water view house in Annapolis, Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Top trending hotels in Royal Oak

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak MD
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 7.8 mi (12.6 km) from Saint Michaels Village and 8.3 mi (13.3 km) from St. Michaels ...
Opens in a new windowRANCH AT ROYAL OAK- Exclusive waterfront pool pier
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$343 per night from 9 Mar to 10 Mar
AU$343
9 Mar - 10 Mar
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital ...
Opens in a new windowHyatt Regency Chesapeake Bay
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
The price is AU$190 per night from 17 Feb to 18 Feb
AU$190
17 Feb - 18 Feb
includes taxes & fees
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and Rod n Reel Charter ...
Opens in a new windowRod 'N' Reel Resort
Save an average of 15% on thousands of hotels when you're signed in
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$214 per night from 12 Feb to 13 Feb
AU$214
12 Feb - 13 Feb
includes taxes & fees
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 ...
Opens in a new windowHyatt Place Kent Narrows & Marina
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.