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Featured Holiday Homes in Royal Oak

Heated pool, sandy beach, pier, and playground set punch point apart!

Heated pool, sandy beach, pier, and playground set punch point apart!

Sherwood
Located in Sherwood, this vacation home is on the waterfront, a 3-minute drive from Goat Island and 7 minutes from Back Creek Community Park.
Heated pool, sandy beach, pier, and playground set punch point apart!
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels
When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Perry Cabin Park and Saint Michaels Town Hall.
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Rising Sun Bay View Cottage

Rising Sun Bay View Cottage

Chesapeake Beach
Located in Chesapeake Beach, this vacation home is on the waterfront, a 1-minute drive from Bruce Gabrielson's Surf Art Gallery and Museum and 6 minutes from ...
Rising Sun Bay View Cottage
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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
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$511 per night from 27 Aug to 28 Aug
AU$511
27 Aug - 28 Aug
includes taxes & fees
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
Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
With a stay at this vacation home in Shady Side, you'll be within a 5-minute drive of Shadyside Park and Captain Avery Museum.
Bay views with kayaks, bikes, fire pit, crabbing and more
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 12 minutes by car from Spocott Windmill.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
St. Michaels Waterfront Home

St. Michaels Waterfront Home

New comb
Located in Easton, this vacation home is on the waterfront, a 4-minute drive from Saint Michaels Village and 5 minutes from St. Michaels Winery.
St. Michaels Waterfront Home
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville
Located in Stevensville, this vacation home is by the ocean, within a 15-minute drive of Romancoke Wharf County Park and Matapeake State Park.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
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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.

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
367 Holiday Homes
Lowest Price
AU$166
Highest Price
AU$511
Popular accommodation
Heated pool, sandy beach, pier, and playground set punch point apart!, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Rising Sun Bay View Cottage, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Relax on Kent Island in 3 Bedroom Home w/Waterview, Bay views with kayaks, bikes, fire pit, crabbing and more, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, St. Michaels Waterfront Home, Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

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$432 per night from 25 Aug to 26 Aug
AU$432
25 Aug - 26 Aug
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 Meredith House.
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$271 per night from 21 Aug to 22 Aug
AU$271
21 Aug - 22 Aug
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 ...
Hyatt Place Kent Narrows & Marina
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is AU$166 per night from 14 Sept to 15 Sept
AU$166
14 Sept - 15 Sept
includes taxes & fees
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
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Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$242 per night from 3 Sept to 4 Sept
AU$242
3 Sept - 4 Sept
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 3 minutes by foot ...
Rod 'N' Reel Resort
Don't see what you're looking for?
See all available properties in Royal Oak
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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.