Book Holiday Homes in Royal Oak

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Featured Holiday Homes in Royal Oak

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
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.3 mi (10.2 km) from Ragged Island and 7.7 mi (12.4 km) from Spocott ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
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.
Walk to Everything House
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Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Matapeake State Park and 6 minutes from Paul Reed Smith Guitars.
Circa 1700 Chesapeake Colonial home on the National Register.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
The price is AU$474 per night from 6 Mar to 7 Mar
AU$474
includes taxes & fees
6 Mar - 7 Mar
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2 out of 5
Cambridge
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Preston
Located in Preston, this vacation home is by the sea, within a 15-minute drive of Gilpin's Point Landing and Williston Lake.
Stylish Home on the Choptank River (with Tidal Beach)
Pet-Friendly Annapolis Home: Walk to Beach!

Pet-Friendly Annapolis Home: Walk to Beach!

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 ...
Pet-Friendly Annapolis Home: Walk to Beach!
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

North Beach
Located in North Beach, this vacation home is within a 10-minute drive of Bayside History Museum and Upper Yough River.
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
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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
279 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$634
Popular accommodation
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Walk to Everything House, Circa 1700 Chesapeake Colonial home on the National Register., ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Stylish Home on the Choptank River (with Tidal Beach), Pet-Friendly Annapolis Home: Walk to Beach!, Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

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$398 per night from 15 Mar to 16 Mar
AU$398
includes taxes & fees
15 Mar - 16 Mar
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
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$634 per night from 23 Feb to 24 Feb
AU$634
includes taxes & fees
23 Feb - 24 Feb
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Inn at Perry Cabin
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$220 per night from 3 Mar to 4 Mar
AU$220
includes taxes & fees
3 Mar - 4 Mar
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
Save an average of 15% on thousands of hotels when you're signed in
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$226 per night from 14 Mar to 15 Mar
AU$226
includes taxes & fees
14 Mar - 15 Mar
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.