Book Holiday Homes in Royal Oak

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Featured Holiday Homes in Royal Oak

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.
Opens in a new windowPrivate 2 Acre Waterfront Family Retreat with Pool & Pier
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton MD
When you stay at this vacation home in Easton, you'll be on the waterfront and 14 minutes by car from Hog Neck Golf Course.
Opens in a new windowBeautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach MD
When you stay at this vacation home in North Beach, you'll be on the beach, within a 10-minute walk of Bayside History Museum and Chesapeake Bay.
Opens in a new windowSweet Bamboo Beach Cottage
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Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home

Annapolis MD
With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowCharming Annapolis WaterVIEW Home
Charming Coastal/Country Home w/3 Acres & Sauna!

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

Stevensville MD
The price is AU$548 per night from 4 May to 5 May
AU$548
4 May - 5 May
includes taxes & fees
Located in Stevensville, this vacation home is within a 5-minute drive of Matapeake State Park and Chesapeake Bay.
Opens in a new windowCharming Coastal/Country Home w/3 Acres & Sauna!
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowBayfront Retreat Near St. Michaels | Private Dock • Sunset Views
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison MD
Located in Madison, this vacation home is on the waterfront, within a 15-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad ...
Opens in a new windowAmazing views waterfront 3-bedroom home in Madison with a 190 foot pier!
Historic Waterfront Estate with Pool & Pet-Friendly  – Perfect for Fall Getaways

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

Oxford MD
Located in Oxford, this vacation home is on the waterfront, within a 10-minute drive of Play Ball Dog Park and Oxford Museum.
Opens in a new windowHistoric Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
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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
335 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$548
Popular accommodation
Private 2 Acre Waterfront Family Retreat with Pool & Pier, Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, Sweet Bamboo Beach Cottage, Charming Annapolis WaterVIEW Home, Charming Coastal/Country Home w/3 Acres & Sauna!, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views, Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!, Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

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$430 per night from 16 Apr to 17 Apr
AU$430
16 Apr - 17 Apr
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
Fully refundableReserve now, pay when you stay
The price is AU$261 per night from 12 Apr to 13 Apr
AU$261
12 Apr - 13 Apr
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
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$160 per night from 12 Apr to 13 Apr
AU$160
12 Apr - 13 Apr
includes taxes & fees
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 ...
Opens in a new windowBest Western Kent Narrows Inn
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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$239 per night from 5 Apr to 6 Apr
AU$239
5 Apr - 6 Apr
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
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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.

Top Picks

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^Subject to availability and chosen travel dates.