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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Royal Oak vacation rentals

Exterior

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 great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is ￥10,750
￥37,692 total
includes taxes & fees
Feb 1 - Feb 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is ￥14,058
￥42,660 total
includes taxes & fees
Feb 8 - Feb 9
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior detail

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

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
North Beach
9.6 out of 10, Exceptional, (4 reviews)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
The price is ￥22,052
￥45,127 total
includes taxes & fees
Jan 30 - Jan 31
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (18 reviews)
"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 ￥12,417
￥49,257 total
includes taxes & fees
Feb 5 - Feb 6
Walk to Beach! King Bed & Free Beach Passes
Outdoor dining

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, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is ￥16,677
￥64,248 total
includes taxes & fees
Jan 30 - Jan 31
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Marina

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)
"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 ￥20,593
￥52,065 total
includes taxes & fees
Feb 2 - Feb 3
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

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 clean, and very comfortable beds."
United States
Edward R.
The price is ￥21,356
￥52,874 total
includes taxes & fees
Feb 2 - Feb 3
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

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 apartment was exceptionally clean and comfortable."
United States
Beth T.
The price is ￥22,652
￥54,409 total
includes taxes & fees
Jan 31 - Feb 1
Station House East: Upscale Loft in the Historic District Cambridge, MD
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is ￥27,565
￥61,198 total
includes taxes & fees
Jan 31 - Feb 1
Beautiful Waterfront Retreat in Cambridge!
Marina

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 ￥22,118
￥53,843 total
includes taxes & fees
Feb 2 - Feb 3
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is ￥23,737
￥38,959 total
includes taxes & fees
Jan 31 - Feb 1
Sailwinds Loft at Cambridge Creek
Marina

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

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very Good, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is ￥18,305
￥45,274 total
includes taxes & fees
Feb 1 - Feb 2
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Smart TV

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 ￥23,293
￥67,232 total
includes taxes & fees
Feb 1 - Feb 2
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (52 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ￥35,222
￥42,692 total
includes taxes & fees
Feb 1 - Feb 2
Waterfront Getaway with Dock
Beach

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 ￥30,628
￥59,575 total
includes taxes & fees
Feb 2 - Feb 3
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Beach nearby, sun loungers, beach towels

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 ￥31,700
￥76,291 total
includes taxes & fees
Feb 3 - Feb 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Dining

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 ￥38,285
￥64,444 total
includes taxes & fees
Jan 30 - Jan 31
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is ￥22,358
￥58,263 total
includes taxes & fees
Feb 8 - Feb 9
Sunset Cottage - West River Access and Views!
Smart TV

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 ￥47,419
￥94,244 total
includes taxes & fees
Feb 9 - Feb 10
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Smart TV

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)
"Amazing news out of the back.Great for kayaking.We brought our own kayaksAnd also use yoursThere were four of usWe also took a nice trip over to Saint Michael’s"
United States
Sandy S.
The price is ￥40,019
￥80,579 total
includes taxes & fees
Feb 4 - Feb 5
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Royal Oak Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"They were very accommodating when we needed to extend our stay because of a blizzard and gave us cupcakes."
Ross 2-night trip
Posted 3 days ago
Rod 'N' Reel Resort

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?

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS): Visitors give good reviews to this Royal Oak vacation home rental, which is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a private yard, and a selection of games so you can immerse yourself in your vacation.

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 Saint Michaels Village and St. Michaels Winery.

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.