Book Holiday Homes in Royal Oak

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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
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
The price is AU$577 per night from 31 Oct to 1 Nov
AU$577
31 Oct - 1 Nov
includes taxes & fees
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
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.
Opens in a new windowSpacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Deale
Located in Deale, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowMillion Dollar View of the Chesapeake Bay
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Opens in a new windowWalk to Everything House
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$452 per night from 16 Nov to 17 Nov
AU$452
16 Nov - 17 Nov
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be a 2-minute walk from Chesapeake Bay and within a 5-minute drive of Romancoke Wharf County Park.
Opens in a new windowRelax on Kent Island in 3 Bedroom Home w/Waterview
Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

Annapolis
With a stay at this vacation home in Annapolis, you'll be on the beach, within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.
Opens in a new windowPrivate Waterfront Woods | Dock, Kayaks, Views
Waterfront- 5-bedroom house with dock in charming North Beach

Waterfront- 5-bedroom house with dock in charming North Beach

2 out of 5
North Beach
When you a stay at this vacation home in North Beach, you'll be on the waterfront, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront- 5-bedroom house with dock in charming North Beach
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 10-minute walk of Bayside History Museum and Chesapeake Bay.
Opens in a new windowSweet Bamboo Beach Cottage
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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
345 Holiday Homes
Lowest Price
AU$168
Highest Price
AU$577
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Million Dollar View of the Chesapeake Bay, Walk to Everything House, Relax on Kent Island in 3 Bedroom Home w/Waterview, Private Waterfront Woods | Dock, Kayaks, Views, Waterfront- 5-bedroom house with dock in charming North Beach, Sweet Bamboo Beach Cottage

Top trending hotels in Royal Oak

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 5.6 mi (9 km) from Oxford Museum and 7.8 mi (12.6 km) from Saint Michaels ...
Opens in a new windowLuxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
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$228 per night from 6 Nov to 7 Nov
AU$228
6 Nov - 7 Nov
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
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is AU$168 per night from 6 Nov to 7 Nov
AU$168
6 Nov - 7 Nov
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 ...
Opens in a new windowSt Michaels Inn
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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$305 per night from 3 Nov to 4 Nov
AU$305
3 Nov - 4 Nov
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.
Opens in a new windowHyatt Regency Chesapeake Bay
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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.