Royal Oak Holiday Rentals

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Holiday Rentals in Royal Oak

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (32)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (211)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (48)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (9)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$840
includes taxes & fees
8 July - 9 July
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$574
includes taxes & fees
6 July - 7 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (132)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (41)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
8.0 out of 10, Very good, (4)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (62)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (39)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is NZ$879
includes taxes & fees
14 July - 15 July
Beautiful Waterfront Retreat in Cambridge!

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (37)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is NZ$733
includes taxes & fees
13 July - 14 July
The Cottage

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (3)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"The location is perfect; we enjoyed evenings sitting by water and relaxing, after a quick few-minute trip to visit St Michael's. The home was perfect for two couples, and can easily support 6 folks.Two bedrooms are masters, and the remaining bedroom is across from the "guest" bathroom. We didn't use cooking utensils, so cannot comment on availability, however, all appliances were modern. We would not hesitate to rent the property again."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Great stay"
The Lazy Crab Beach House - Free beach passes

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (119)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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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Frequently asked questions

Can I find a holiday rental in Royal Oak?

Yes, there are holiday rentals close to the most popular sights in Royal Oak, or you can select a more secluded option if you're looking for a relaxing stay. Royal Oak is known for its waterfront.

What are some of the best holiday rentals that Royal Oak has to offer?

Private Cottage on gated estate: This holiday home rental outside of Royal Oak is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Royal Oak?

Expedia has 10 holiday rentals for your stay in Royal Oak.

What can I see and do in Royal Oak?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Gerry Boyle Park at Great Marsh. In the wider area, you’ll find Oxford Museum and Saint Michaels Village.

What are holiday rentals like in Royal Oak?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Royal Oak. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips or small group gatherings.