Book Holiday Homes in Royal Oak

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Featured Holiday Homes in Royal Oak

Caribbean Pool Home <1 mile from Matapeake Beach!

Caribbean Pool Home <1 mile from Matapeake Beach!

Stevensville
The price is AU$1,489 per night from 24 Jun to 25 Jun
AU$1,489
per night
24 Jun - 25 Jun
When you stay at this vacation home in Stevensville, you'll be near the beach and 7 minutes by foot from Matapeake State Park.
Caribbean Pool Home <1 mile from Matapeake Beach!
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 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

Annapolis
Located in Annapolis, this vacation home is on the waterfront, within a 10-minute drive of Bay Bridge Market Place Shopping Center and Historic Mount Moriah ...
NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
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Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

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 Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

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 ...
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
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
The Normandy Cottage ~ Charming Getaway ~  On The Shores Of The Chesapeake!

The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!

North Beach
Located in North Beach, this vacation home is by the sea, a 3-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake Beach Water ...
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Blocks to the Boardwalk!

Blocks to the Boardwalk!

North Beach
A stay at this vacation home places you in the heart of North Beach, just a 4-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake ...
Blocks to the Boardwalk!
Private Waterview Estate with 4 bedroom Suites & Hot Tub

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side
Located in Churchton, this vacation home is on the waterfront, within a 10-minute drive of Franklin Point State Park and Shadyside Park.
Private Waterview Estate with 4 bedroom Suites & Hot Tub
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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
290 Holiday Homes
Lowest Price
AU$249
Highest Price
AU$1,489
Popular accommodation
Caribbean Pool Home <1 mile from Matapeake Beach!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, NEW, cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard, The Lazy Crab Beach House - Free beach passes , The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake! , Blocks to the Boardwalk!, Private Waterview Estate with 4 bedroom Suites & Hot Tub

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$301 per night from 8 Jul to 9 Jul
AU$301
per night
8 Jul - 9 Jul
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 refundable
The price is AU$288 per night from 17 Jun to 18 Jun
AU$288
per night
17 Jun - 18 Jun
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 refundableReserve now, pay when you stay
The price is AU$249 per night from 7 Jul to 8 Jul
AU$249
per night
7 Jul - 8 Jul
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

3 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$317 per night from 17 Jun to 18 Jun
AU$317
per night
17 Jun - 18 Jun
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.