Royal Oak Vacation Rentals

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Our top choices for Royal Oak vacation 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 great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is CA $131
CA $389 total
includes taxes & fees
Feb 17 - Feb 18
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 CA $203
CA $492 total
includes taxes & fees
Feb 11 - Feb 12
Station House East: Upscale Loft in the Historic District Cambridge, MD

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 CA $146
CA $406 total
includes taxes & fees
Feb 22 - Feb 23
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)
"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 CA $191
CA $478 total
includes taxes & fees
Feb 9 - Feb 10
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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 CA $198
CA $487 total
includes taxes & fees
Feb 16 - Feb 17
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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 CA $136
CA $562 total
includes taxes & fees
Feb 11 - Feb 12
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

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 CA $205
CA $494 total
includes taxes & fees
Feb 9 - Feb 10
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

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 CA $112
CA $448 total
includes taxes & fees
Feb 16 - Feb 17
Walk to Beach! King Bed & Free Beach Passes

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 CA $171
CA $413 total
includes taxes & fees
Feb 10 - Feb 11
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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 CA $215
CA $610 total
includes taxes & fees
Feb 9 - Feb 10
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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 CA $274
CA $536 total
includes taxes & fees
Feb 9 - Feb 10
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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 CA $302
CA $705 total
includes taxes & fees
Feb 9 - Feb 10
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 CA $212
CA $346 total
includes taxes & fees
Feb 9 - Feb 10
Sailwinds Loft at Cambridge Creek

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 CA $315
CA $380 total
includes taxes & fees
Feb 9 - Feb 10
Waterfront Getaway with Dock

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 CA $342
CA $577 total
includes taxes & fees
Feb 9 - Feb 10
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
Deale
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful property! Water on two sides, lots of outdoor space , we had 11 people from 2-92 years staying for almost a week and had a great time. Wonderful sitting areas and screened porch. We crabbed, kayaked, had a campfire grilled. Relaxing getaway"
United States
Jody P.
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

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 CA $425
CA $845 total
includes taxes & fees
Feb 9 - Feb 10
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is CA $219
CA $557 total
includes taxes & fees
Feb 16 - Feb 17
Sunset Cottage - West River Access and Views!

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is CA $410
CA $594 total
includes taxes & fees
Feb 28 - Mar 1
40' Bristol sailboat with spectacular views

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 CA $338
CA $656 total
includes taxes & fees
Feb 10 - Feb 11
Beautiful Waterfront Retreat in Cambridge!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Royal Oak. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

The Blue Crab Beach House - Free beach passes : Visitors like this Royal Oak vacation home rental. It is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a private yard and a selection of games.

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.