Royal Oak Holiday Rentals

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Our top choices for Royal Oak holiday rentals

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is NZ$450
includes taxes & fees
12 Apr - 13 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is NZ$445
includes taxes & fees
7 Apr - 8 Apr
Sailwinds Loft at Cambridge Creek

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is NZ$1,081
includes taxes & fees
21 Apr - 22 Apr
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (10 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is NZ$1,065
includes taxes & fees
7 Apr - 8 Apr
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"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 NZ$726
includes taxes & fees
7 Apr - 8 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is NZ$1,160
includes taxes & fees
14 Apr - 15 Apr
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (11 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is NZ$740
includes taxes & fees
14 Apr - 15 Apr
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is NZ$719
includes taxes & fees
14 Apr - 15 Apr
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is NZ$433
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
The price is NZ$708
includes taxes & fees
14 Apr - 15 Apr
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$769
includes taxes & fees
7 Apr - 8 Apr
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is NZ$753
includes taxes & fees
7 Apr - 8 Apr
40' Bristol sailboat with spectacular views

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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$839
includes taxes & fees
20 Apr - 21 Apr
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is NZ$743
includes taxes & fees
14 Apr - 15 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is NZ$862
includes taxes & fees
7 Apr - 8 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is NZ$642
includes taxes & fees
12 Apr - 13 Apr
Walk to Beach! King Bed & Free Beach Passes

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (1 review)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is NZ$817
includes taxes & fees
14 Apr - 15 Apr
Sunset Cottage - West River Access and Views!

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (54 reviews)
"Great place, will stay again"
United States
Matt S.
The price is NZ$482
includes taxes & fees
29 Apr - 30 Apr
Waterfront Getaway with Dock

Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach
Stevensville
8.0 out of 10, Very good, (3 reviews)
"Great location! Clean! Parking was very easy!"
United States
Susan P.
The price is NZ$2,032
includes taxes & fees
13 Apr - 14 Apr
Kent Island Luxary Home W/ Pool and walking distance from the beach

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is NZ$587
includes taxes & fees
7 Apr - 8 Apr
Waterfront Unit | Dock, Kayaks & SUPs Included
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

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 favorite 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 depends 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 NZ$433 per night. Entering your travel dates in the search wizard you might find 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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This holiday home rental outside of Royal Oak is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

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.