Royal Oak Vacation Rentals

  • 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

Our top choices for Royal Oak vacation rentals

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 ¥39,933
¥67,218 total
includes taxes & fees
Mar 17 - Mar 18
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is ¥25,014
¥71,126 total
includes taxes & fees
Mar 17 - Mar 18
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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 ¥26,355
¥58,074 total
includes taxes & fees
Mar 17 - Mar 18
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is ¥27,953
¥62,308 total
includes taxes & fees
Mar 17 - Mar 18
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

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 ¥24,758
¥39,281 total
includes taxes & fees
Mar 17 - Mar 18
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 ¥41,905
¥84,547 total
includes taxes & fees
Mar 17 - Mar 18
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 ¥26,355
¥60,614 total
includes taxes & fees
Mar 18 - Mar 19
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (53 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ¥36,738
¥43,006 total
includes taxes & fees
Mar 17 - Mar 18
Waterfront Getaway with Dock

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 ¥49,654
¥98,686 total
includes taxes & fees
Mar 17 - Mar 18
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!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is ¥39,613
¥71,281 total
includes taxes & fees
Mar 17 - Mar 18
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, accurate to the listing and to prior feedback from other visitors. We loved the area; very quaint and cute. We enjoyed our stay and would recommend it to anyone looking for a cozy place to stay. "
United States
Amanda S.
The price is ¥23,720
¥57,144 total
includes taxes & fees
Mar 19 - Mar 20
Station House East: Upscale Loft in the Historic District Cambridge, MD

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
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ¥38,096
¥86,039 total
includes taxes & fees
Mar 17 - Mar 18
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 ¥15,844
¥65,122 total
includes taxes & fees
Mar 17 - Mar 18
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 ¥18,281
¥58,116 total
includes taxes & fees
Mar 18 - Mar 19
Walk to Beach! King Bed & Free Beach Passes

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is ¥47,919
¥69,249 total
includes taxes & fees
Mar 17 - Mar 18
40' Bristol sailboat with spectacular views

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
9.6 out of 10, Exceptional, (5 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is ¥33,863
¥64,339 total
includes taxes & fees
Mar 30 - Mar 31
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 ¥27,154
¥70,045 total
includes taxes & fees
Mar 23 - Mar 24
Family Beach House: Spacious Deck, Grill & Views

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is ¥31,946
¥72,492 total
includes taxes & fees
Mar 19 - Mar 20
Sunset Cottage - West River Access and Views!

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 ¥10,969
¥39,733 total
includes taxes & fees
Mar 17 - Mar 18
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
The price is ¥40,891
¥51,315 total
includes taxes & fees
Apr 12 - Apr 13
Sunset Breezes - quiet waterfront retreat
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

Search for holiday rentals in Royal Oak on Expedia! You can easily find your home rentals, villas, holiday apartments in Royal Oak using one of the methods below:

  • View our selection of featured holiday rentals in Royal Oak
  • Use the map to find apartments and other holiday homes in the Royal Oak neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Royal Oak while they last

Look no further and take a look at our great range of rental properties in Royal Oak!

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Royal Oak?

Yes, you can find vacation rentals near popular attractions in Royal Oak, or you can select a more remote option if you're looking for a relaxing stay. Royal Oak is known for its waterfront.

What's the top vacation rental in Royal Oak?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: You might want to consider this vacation home rental near Royal Oak, which is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in Royal Oak?

Expedia has 10 vacation 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 larger area, you’ll find Oxford Museum and Saint Michaels Village.

What are vacation rentals like in Royal Oak?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Royal Oak. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.