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Royal Oak Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Royal Oak holiday 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, (48 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$762
HK$2,267 total
includes taxes & fees
26 Jul - 27 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (37 reviews)
"Can’t wait to come back!"
United States
Tiffany K.
The price is HK$1,215
HK$1,995 total
includes taxes & fees
27 Jul - 28 Jul
Sailwinds Loft at Cambridge Creek
1 bedroom, iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is HK$1,121
HK$2,070 total
includes taxes & fees
29 Jul - 30 Jul
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
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, (9 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$1,647
HK$3,183 total
includes taxes & fees
27 Jul - 28 Jul
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (24 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is HK$2,078
HK$3,940 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is HK$995
HK$2,538 total
includes taxes & fees
26 Jul - 27 Jul
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
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, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$2,039
HK$3,898 total
includes taxes & fees
28 Jul - 29 Jul
The Drinking Gourd: Stunning Penthouse in Historic Downtown 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, (12 reviews)
"Great space. Great location for exploring Cambridge on foot. Check-in easy. Everything clean. Everything works."
United States
Peter G.
The price is HK$2,156
HK$3,915 total
includes taxes & fees
28 Jul - 29 Jul
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Beach nearby

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is HK$1,838
HK$4,055 total
includes taxes & fees
13 Aug - 14 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (41 reviews)
"Lovely, spacious home in a quiet setting. Ken Island is a beautiful, relaxing spot. Adam was so accommodating and easy to communicate with. The house is well stocked, clean, and comfortable. You’ll enjoy your stay there!"
United States
Susan
The price is HK$1,068
HK$2,649 total
includes taxes & fees
4 Aug - 5 Aug
Charming Coastal/Country Home w/3 Acres & Sauna!
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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is HK$3,447
HK$5,823 total
includes taxes & fees
26 Jul - 27 Jul
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Terrace/patio

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
The price is HK$1,299
HK$2,830 total
includes taxes & fees
28 Jul - 29 Jul
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Coffee/tea maker, fridge, microwave, oven

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (62 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is HK$1,803
HK$2,178 total
includes taxes & fees
17 Aug - 18 Aug
Waterfront Getaway with Dock
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is HK$3,442
HK$4,328 total
includes taxes & fees
29 Jul - 30 Jul
Sunset Breezes - quiet waterfront retreat
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
9.0 out of 10, Wonderful, (13 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 HK$2,849
HK$5,339 total
includes taxes & fees
29 Jul - 30 Jul
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Marina

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is HK$2,548
HK$5,193 total
includes taxes & fees
27 Jul - 28 Jul
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,137
HK$3,589 total
includes taxes & fees
24 Jul - 25 Jul
Plum Point Cottage #17
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$2,282
HK$5,022 total
includes taxes & fees
12 Aug - 13 Aug
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is HK$2,564
HK$4,716 total
includes taxes & fees
28 Jul - 29 Jul
Sunset Cottage - West River Access and Views!
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
9.6 out of 10, Exceptional, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,858
HK$5,511 total
includes taxes & fees
4 Aug - 5 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great value. Clean. Comfortable bed. Very nice staff. Nice swimming pool"
Cathy L 2-night trip
Posted 7 hours ago
St Michaels Inn

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!

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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Royal Oak is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Royal Oak?

Expedia has 12 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.