Royal Oak Holiday Rentals

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Our top choices for Royal Oak holiday rentals

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$993
includes taxes & fees
20 Feb - 21 Feb
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$683
includes taxes & fees
20 Feb - 21 Feb
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is NZ$629
includes taxes & fees
23 Feb - 24 Feb
Sunset Cottage - West River Access and 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)
"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 NZ$641
includes taxes & fees
16 Mar - 17 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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 NZ$709
includes taxes & fees
22 Feb - 23 Feb
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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

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 NZ$598
includes taxes & fees
3 Mar - 4 Mar
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$592
includes taxes & fees
2 Mar - 3 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City 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)
"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$578
includes taxes & fees
3 Mar - 4 Mar
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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.
Beautiful Waterfront Retreat in Cambridge!

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)
"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 NZ$526
includes taxes & fees
22 Feb - 23 Feb
Walk to Beach! King Bed & Free Beach Passes

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 NZ$676
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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$864
includes taxes & fees
21 Feb - 22 Feb
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 NZ$454
includes taxes & fees
22 Feb - 23 Feb
Waterfront Getaway with Dock

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 NZ$401
includes taxes & fees
22 Feb - 23 Feb
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 NZ$848
includes taxes & fees
2 Mar - 3 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (33 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is NZ$423
includes taxes & fees
22 Feb - 23 Feb
Charming Coastal/Country Home w/3 Acres & Sauna!

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 NZ$414
includes taxes & fees
20 Feb - 21 Feb
Sailwinds Loft at Cambridge Creek

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 NZ$584
includes taxes & fees
21 Feb - 22 Feb
Station House East: Upscale Loft in the Historic District Cambridge, MD

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is NZ$710
includes taxes & fees
28 Feb - 1 Mar
40' Bristol sailboat with spectacular views
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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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$423 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?

The Blue Crab Beach House - Free beach passes : This holiday home rental outside of Royal Oak is located near the beach, and has a fireplace, a patio and a BBQ 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 garden and a selection of games.

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 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.