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$1,166 per night from 28 May to 29 May
AU$1,166
per night
28 May - 29 May
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!
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!
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
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The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
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$438 per night from 28 May to 29 May
AU$438
per night
28 May - 29 May
Located in Stevensville, this vacation home is within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.
Relax on Kent Island in 3 Bedroom Home w/Waterview
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
Charming Cottage with Hot Tub 1 Block from the Bay

Charming Cottage with Hot Tub 1 Block from the Bay

Annapolis
The price is AU$950 per night from 27 May to 28 May
AU$950
per night
27 May - 28 May
With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 10-minute drive of Bay Bridge Market Place Shopping Center and Historic ...
Charming Cottage with Hot Tub 1 Block from the Bay
Newly Remodeled Home, 10 Minute Walk to Downtown

Newly Remodeled Home, 10 Minute Walk to Downtown

Cambridge
With a stay at this vacation home in Cambridge, you'll be within a 15-minute walk of Brannock Maritime Museum and Great Marsh Park.
Newly Remodeled Home, 10 Minute Walk to Downtown
Peaceful Queenstown Home w/ Deck & Grill!

Peaceful Queenstown Home w/ Deck & Grill!

Queenstown
With a stay at this vacation home in Queenstown, you'll be within a 10-minute drive of Queenstown Premium Outlets and Queenstown Harbor Golf Links.
Peaceful Queenstown Home w/ Deck & Grill!
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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
239 Holiday Homes
Lowest Price
AU$186
Highest Price
AU$1,166
Popular accommodation
Caribbean Pool Home <1 mile from Matapeake Beach!, The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake! , Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, The Blue Crab Beach House - Free beach passes , Relax on Kent Island in 3 Bedroom Home w/Waterview, The Lazy Crab Beach House - Free beach passes , Charming Cottage with Hot Tub 1 Block from the Bay, Newly Remodeled Home, 10 Minute Walk to Downtown, Peaceful Queenstown Home w/ Deck & Grill!

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$307 per night from 27 May to 28 May
AU$307
per night
27 May - 28 May
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
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$186 per night from 2 Jun to 3 Jun
AU$186
per night
2 Jun - 3 Jun
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
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$314 per night from 3 Jun to 4 Jun
AU$314
per night
3 Jun - 4 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
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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$215 per night from 28 May to 29 May
AU$215
per night
28 May - 29 May
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.