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Top Holiday Rentals in Royal Oak

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, (45)
"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

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (61)
"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

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

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (182)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (31)
"Great location, close to the beach and restaurant. Cozy and comfortable, with a beautiful view of sunset. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels

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

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

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 £239
includes taxes & fees
26 Jun - 27 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (53)
"Great and comfortable stay! Beautiful historic house and property Owners were so friendly and helpful"
Circa 1700 Chesapeake Colonial home on the National Register.

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 £373
includes taxes & fees
26 Jun - 27 Jun
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
The price is £230
includes taxes & fees
8 Jul - 9 Jul
Cass-N-Reel Luxury Houseboat

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is £336
includes taxes & fees
7 Jul - 8 Jul
The Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (6)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

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

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (33)
"Great stay"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

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

10.0 out of 10, Exceptional, (131)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (96)
"This is a great getaway place!! Very nice on the water. Lots to do in the area! Tiki Bars restaurants must stop while traveling or vacationing!"
Cass-Away Luxury Houseboat
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.