Royal Oak Holiday Rentals

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Holiday Rentals in Royal Oak

Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
10.0 out of 10, Exceptional, 3 reviews
"All day views. Sunrises and sunsets. Quiet and easy to get to. Beautiful property and the house is perfect for a small group. Dock is great for crabbing and fishing. Will be back for sure!"
Minutes from Downtown Easton and St. Michaels | Charming | 4000 ft of Shoreline
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 187 reviews
"Several family members and I went on a fishing trip out of Edgewater. We stayed in this wonderful cottage on the water. The house was immaculate and everything we needed aside from food was provided. The check in and check out were very simple and the host gave us contact information in case we needed anything. The location and overall property could not have been any better. We would definitely stay here again."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 7 reviews
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, 3 reviews
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is AU$1,721
per night
17 June - 18 June
Waterfront Cottage on the Eastern Shore
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, 19 reviews
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is AU$390
per night
17 June - 18 June
Relax on Kent Island in 3 Bedroom Home w/Waterview
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, 43 reviews
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is AU$1,262
per night
11 July - 12 July
Charming Annapolis WaterVIEW Home
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 106 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, 9 reviews
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 18 reviews
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is AU$767
per night
16 June - 17 June
Beautiful Waterfront Retreat in Cambridge!
Walk to Everything House
10.0 out of 10, Exceptional, 64 reviews
"The house was perfectly located in town in St. Michael’s with off street parking as a bonus. Despite the weather being cold and rainy, we had a lovely time in charming St. Michaels. It was a delightful spot for our annual girls weekend."
Walk to Everything House
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, 81 reviews
"We had a bit of trouble figuring out the TV, and Kirby was most helpful and responsive, even at 8:30pm! The proximity of several walkable seafood restaurants was handy, and tasteful. The traffic on both road and water was actually entertaining, to the point of getting unduly mesmerized by the drawbridge routine. For a nice touch, a great blue heron flew right under our kitchen window."
Cass-Away Luxury Houseboat
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 39 reviews
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 109 reviews
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
9.6 out of 10, Exceptional, 12 reviews
"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 198 reviews
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, 155 reviews
"Cute, quaint, conveniently located home. Lovely stay!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, 74 reviews
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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See all available properties in Royal Oak
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 Home Travel Info

Other types of properties in Royal Oak you may be interested in

Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, 1,001 reviews
"I loved the sunset, the cleaner, the clean smoke and marihuana free air and the food options. I loved everything about this place. It is a perfect place for a retirement. "
The price is AU$300
per night
8 July - 9 July
Hyatt Regency Chesapeake Bay
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, 322 reviews
"Excellent venue"
The price is AU$287
per night
17 June - 18 June
Hyatt Place Kent Narrows & Marina
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, 1,000 reviews
"The check-in was fine. The gentleman was very friendly at the desk. The room was average. It appeared clean initially, but the shower did not drain And it smelled when you took a shower because the drain was backing up. Also, there was no stopper in the sink and there was a smell coming from the drain. When I turned down the bed at night, there was a blood stain on the sheets, which was really unappealing to see the least. They didn’t not have a phone in the room to contact the front desk. I had...
The price is AU$248
per night
14 July - 15 July
St Michaels Inn
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.

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$390 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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This holiday home rental outside of Royal Oak offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. 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 8 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 Long Wharf Park. In the wider area, you’ll find St. Michaels Winery and Avalon Theatre.

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.

Recent reviews of Royal Oak properties
Expedia verified reviews