Royal Oak Holiday Rentals

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Check prices for these dates

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Holiday Rentals in Royal Oak

Dining
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
10.0 out of 10, Exceptional, (27)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
Kate F.
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Fridge, microwave, oven, stovetop
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
10.0 out of 10, Exceptional, (90)
"This property is even prettier in person!! We have a huge extended family and there was plenty of space for everyone. The host and property manager both made themselves available to answer any questions and responded very quickly. Excellent trip - we would love to stay again in the future!"
Christine P.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Outdoor dining
The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (11)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (14)
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place! "
Michael T.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Marina
Floating 2 bed 2 bath condo stunning views of the bay
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
Aaron D.
The price is AU$472
includes taxes & fees
27 Oct - 28 Oct
Waterfront Getaway, Dock Your Boat & Play!
Marina
Cass-N-Reel Luxury Houseboat
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (42)
"Great location - very convenient to 50 and restaurants - very clean - greatly appreciated the water and potato chips"
dewey b.
Cass-N-Reel Luxury Houseboat
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is AU$445
includes taxes & fees
27 Oct - 28 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
Dining
Million Dollar View of the Chesapeake Bay
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
Melissa G.
Million Dollar View of the Chesapeake Bay
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Fridge, microwave, oven, stovetop
Walk to Everything House
Walk to Everything House
10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Terry K.
Walk to Everything House
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (219)
"Very nice place, we will be visiting again!"
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (259)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Catherine W.
Family and Pet-Friendly, Waterfront with Pier
Outdoor dining
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (191)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Joan A.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Ronald S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Interior
Private Waterfront Woods | Dock, Kayaks, Views
Private Waterfront Woods | Dock, Kayaks, Views
9.2 out of 10, Wonderful, (29)
"This place was great for 10 us (5 adults and 5 kids). Plenty of fun activities for the kids, and it was clean and comfortable for the adults. Check-in and communication was easy. No complaints. Thank you for sharing your wonderful property!"
Roman R.
Private Waterfront Woods | Dock, Kayaks, Views
Fridge, microwave, oven, stovetop
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
10.0 out of 10, Exceptional, (41)
"House was beautiful! Right on the bay and easily accommodated our group. "
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
Angie R.
The price is AU$455
includes taxes & fees
19 Oct - 20 Oct
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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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Top Royal Oak Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Very professionally cleaned. Safe."
Willie Frank 2-night trip
Posted 2 days ago
Hyatt Regency Chesapeake Bay

Find out more about Royal Oak

Everything you need to know about Royal Oak holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Royal Oak holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Royal Oak holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Royal Oak holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Royal Oak. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Royal Oak holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Royal Oak holiday rentals we have selected for you start as low as AU$445 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Royal Oak rentals

At Expedia, we put the best Royal Oak holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Royal Oak rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Royal Oak holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Royal Oak. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub: This holiday home rental outside of Royal Oak is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Royal Oak?

Expedia has 11 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.