Royal Oak holiday rentals

We found 136 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Royal Oak that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you need and want for your stay, including Wi-Fi and parking. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Royal Oak

Showing deals for:13 Nov - 20 Nov

Dining table- seats 10!
Pool
View from Pier back to house!
View from Foyer into Great Room
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,138
for 7 nights, 1 home
AU$1,591 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
View of St Michaels Harbor from french doors in Living Room, and from Side Patio
View of Side of Harrison House and St. Michaels Harbor from Locust Street
Rear Porch for relaxing or for barbecues!
View of St. Michaels Harbor from Town Park in front of Thomas Harrison House
Exceptional
(142 reviews)

Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!

St. Michaels

8% off
AU$7,506
for 7 nights, 1 home
AU$1,072 per night
includes taxes & fees
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
Sit and stay a while!
View down the lane
Custom kitchen
Dining Room - Seats 6
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,853
for 7 nights, 1 cottage
AU$408 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Interior
Dining
Living area
Private kitchen
Exceptional
(10 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,104
for 7 nights, 1 cottage
AU$586 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Interior
Be ready to float! Bring your own inner tubes and tennis shoes!
Exterior detail
Living area
Exceptional
(143 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,923
for 7 nights, 1 cottage
AU$418 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Interior
Living area
Property grounds
Exterior
Exceptional
(406 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,936
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Terrace/patio
Living area
Interior
Living area
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels

17% off
AU$3,276
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
St. Michaels Harbor from Park down street
Park half block from house
Front and side view of Blades House from Locust St.
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
AU$4,097
for 7 nights, 1 cottage
AU$585 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The waterfront setting of Royal Oak is ready to explore

Learn about the unique charm of Royal Oak with a stay in a holiday home rental. One of the city's many top draws is its boating. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Royal Oak

Do you want to find things to do while you're in the area? Venture out of your holiday home and check out everything that makes Royal Oak a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (4.9 mi / 7.8 km)
  • Talbot Massage (8.9 mi / 14.4 km)
  • Easton Cycle and Sport (9 mi / 14.5 km)
  • Hog Neck Golf Course (11.2 mi / 18.1 km)
  • Phillips Wharf Environmental Center (6.7 mi / 10.8 km)
  • Bay Country Shop (13.3 mi / 21.5 km)

Exploring the natural features in Royal Oak

Whether you're an outdoor enthusiast or just want to take in the scenery, Royal Oak is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Gerry Boyle Park at Great Marsh (11.2 mi / 18 km)
  • Long Wharf Park (11.8 mi / 18.9 km)
  • Chesapeake Bay Environmental Center (16.4 mi / 26.3 km)
  • Northern Chesapeake Bay (19 mi / 30.6 km)
  • Blackwater National Wildlife Refuge (20.6 mi / 33.1 km)
  • Romancoke Wharf County Park (13.6 mi / 21.8 km)

Transport options to and around Royal Oak

The nearest airport is in Easton, MD (ESN-Easton - Newnam), located 10.3 mi (16.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 45.1 mi (72.6 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Royal Oak?
According to our data, houses are the most sought-after type of property in Royal Oak. But that goes without saying, everyone's idea of the perfect stay is bound to be different. Stayz has holiday homes in a variety of sizes and shapes, and we'll help you find the perfect fit.
How much does it cost to rent a holiday home in Royal Oak?
The average price for a holiday home in Royal Oak is based on a number of factors, including season, length of stay and property type. Whether you're dreaming about a sprawling villa with lots of space or a quaint cottage just for the two of you, just add your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Royal Oak?
The average price for a holiday home by the beach in Royal Oak will depend on when you'll be there and the size and style of property you're searching for. You can find prices easily and quickly on Stayz by entering your travel dates. Then use our filter tool to select the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Royal Oak?
Pack a suitcase and a bone for your canine companion because Royal Oak has 11 holiday homes that throw out the welcome mat to pets. Let your furriest pal have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Royal Oak?
Add a whole other level of fun to your adventure by booking one of the seven houses with a private pool in Royal Oak. Use our search filter to find properties with pools on Stayz, then spend your days splashing around in a swimming pool that's only for you.
What are popular home amenities in Royal Oak?
The most popular home amenities people look for in Royal Oak are a fireplace, a barbecue grill and a chef. Whether you're hitting the road with your besties, family or even pets, Stayz holiday homes have the best amenities for hanging out with the people who matter most.
Are there large group holiday homes in Royal Oak?
Choose from five holiday homes in Royal Oak that can host a group of 10 or more guests. Whether you're organising time away with extended family or a celebration like an anniversary, there's plenty of space to get your loved ones together under the same roof.
Are there holiday homes in Royal Oak that welcome kids?
Bring the whole group together for an epic adventure in Royal Oak at one of our 11 family-friendly properties. A lot of these stays provide amenities that are great for getaways with youngsters, including kitchens, bunk beds and outdoor spaces. Simply check the "Properties good for families" filter and decide on your favourite.
What are the top attractions for families in Royal Oak?
Keeping the kids occupied during your Royal Oak holiday is easy with these cool family-friendly attractions:
  • Chesapeake Bay Maritime Museum
  • Oxford Museum
  • St. Michaels Museum
Are there holiday homes with WiFi in Royal Oak?
Pick from nine holiday homes with WiFi in Royal Oak. If you want to disconnect from the world on your escape, but still want to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Royal Oak?
Select your travel dates and then use the filter tool to see holiday homes with ac in Royal Oak on Stayz. With 11 air-conditioned properties to choose from here, you can enjoy a cool and comfortable break.
How old do you have to be to rent a holiday home in Royal Oak?
The minimum age is typically 16, 18 or 21. It can vary across properties on Stayz, so look at the rules of your chosen Royal Oak stay before booking your stay.
How long can I rent a holiday home in Royal Oak for?
How long you can rent a holiday home in Royal Oak is up to the property. Simply enter your selected dates to view a list of options offering extended stays. With many creature comforts like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover the perfect place to call your home away from home in Royal Oak.

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