Royal Oak Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Royal Oak

Station House East: Upscale Loft in the Historic District Cambridge, MD

Downtown Cambridge
10.0 out of 10, Exceptional, (6)
The price is AU$394
includes taxes & fees
12 Dec - 13 Dec
Station House East: Upscale Loft in the Historic District Cambridge, MD

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property
North Beach
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is AU$422
includes taxes & fees
10 Dec - 11 Dec
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

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

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AU$378
includes taxes & fees
8 Dec - 9 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!

Walk to Beach! King Bed & Free Beach Passes

North Beach
10.0 out of 10, Exceptional, (16)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$500
includes taxes & fees
10 Dec - 11 Dec
Walk to Beach! King Bed & Free Beach Passes

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is AU$1,348
includes taxes & fees
9 Dec - 10 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is AU$528
includes taxes & fees
7 Dec - 8 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$619
includes taxes & fees
7 Dec - 8 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$388
includes taxes & fees
11 Dec - 12 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
The price is AU$649
includes taxes & fees
15 Dec - 16 Dec
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is AU$540
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Just what we were looking for. Appreciated the little touches such as already baited crab traps and the complimentary smores kit. "
United States
Dan K.
The price is AU$577
includes taxes & fees
9 Dec - 10 Dec
Beautiful Waterfront Retreat in Cambridge!

Sailwinds Loft at Cambridge Creek

Cambridge
10.0 out of 10, Exceptional, (23)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is AU$388
includes taxes & fees
12 Dec - 13 Dec
Sailwinds Loft at Cambridge Creek

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Downtown Cambridge
8.8 out of 10, Excellent, (5)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is AU$452
includes taxes & fees
17 Dec - 18 Dec
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$637
includes taxes & fees
16 Dec - 17 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Waterfront Getaway with Dock

Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is AU$425
includes taxes & fees
10 Dec - 11 Dec
Waterfront Getaway with Dock

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is AU$547
includes taxes & fees
7 Dec - 8 Dec
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$701
includes taxes & fees
7 Dec - 8 Dec
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick
9.6 out of 10, Exceptional, (5)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AU$558
includes taxes & fees
17 Dec - 18 Dec
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is AU$1,006
includes taxes & fees
15 Dec - 16 Dec
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is AU$600
includes taxes & fees
7 Dec - 8 Dec
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Royal Oak Hotel Reviews

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$577 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?

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS): This highly rated holiday home rental in 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 6 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 private garden and a selection of games 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 Saint Michaels Village and St. Michaels Winery.

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.