Book Holiday Homes in Royal Oak

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Featured Holiday Homes in Royal Oak

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
Stay at this vacation home in Anne Arundel County. Enjoy free WiFi, private pools, and a sauna. Popular attractions Upper Yough River and Bayside History Museum ...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
Stay at this vacation home in Shady Side. Enjoy a water park, patios, and cable/satellite TV service. Popular attractions Franklin Point State Park and Shadyside ...
Calloway Drive Retreat | House in Shady Side
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
Stay at this vacation home in St. Michaels. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions St. Michaels Museum and ...
Dollhouse in Central Historic St Michaels
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Private Waterfront Woods | Dock, Kayaks, Views

Private Waterfront Woods | Dock, Kayaks, Views

Annapolis
Book a stay at this beach vacation home in Annapolis. Enjoy a beach locale, a garden, and patios. Popular attractions Annapolis Golf Club and Bay Ridge Beach ...
Private Waterfront Woods | Dock, Kayaks, Views
Relax on Kent Island in 3 Bedroom Home w/Waterview

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
The price is NZ$461 per night from 5 Jan to 6 Jan
NZ$461
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Stevensville. Enjoy free WiFi, a garden, and patios. Popular attraction Matapeake State Park is located nearby.
Relax on Kent Island in 3 Bedroom Home w/Waterview
Walk to Everything House

Walk to Everything House

Saint Michaels
Stay at this vacation home in St. Michaels. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions St. Michaels Museum and ...
Walk to Everything House
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
Book a stay at this family-friendly vacation home in Royal Oak. Enjoy free WiFi, private pools, and a garden. Popular attractions Oxford Museum and St. Michaels ...
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Private Waterfront Retreat with Pool, Hot Tub and Game Room

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing
Book a stay at this beach vacation home in Tracys Landing. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Upper Yough River and Bayside History ...
Private Waterfront Retreat with Pool, Hot Tub and Game Room
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

North Beach
Stay at this vacation home in North Beach. Enjoy air conditioning. Popular attractions Bayside History Museum and Chesapeake Beach Water Park are located ...
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
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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.

Royal Oak Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Royal Oak vacation homes are the perfect way for you to wing it.

Holiday houses in Royal Oak let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Royal Oak in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Royal Oak adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Royal Oak with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Royal Oak vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Royal Oak Holiday Homes essential information

Accommodation
286 Holiday Homes
Lowest Price
NZ$220
Highest Price
NZ$781
Popular accommodation
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Calloway Drive Retreat | House in Shady Side, Dollhouse in Central Historic St Michaels, Private Waterfront Woods | Dock, Kayaks, Views, Relax on Kent Island in 3 Bedroom Home w/Waterview, Walk to Everything House, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Private Waterfront Retreat with Pool, Hot Tub and Game Room, Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Top trending hotels in Royal Oak

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is NZ$404 per night from 13 Jan to 14 Jan
NZ$404
includes taxes & fees
13 Jan - 14 Jan 2025
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Hyatt Regency Chesapeake Bay
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is NZ$232 per night from 25 Dec to 26 Dec
NZ$232
includes taxes & fees
25 Dec - 26 Dec
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Hyatt Place Kent Narrows & Marina
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is NZ$781 per night from 9 Jan to 10 Jan
NZ$781
includes taxes & fees
9 Jan - 10 Jan 2025
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Inn at Perry Cabin
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Rod 'N' Reel Resort

Rod 'N' Reel Resort

3 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is NZ$220 per night from 6 Jan to 7 Jan
NZ$220
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this 3-star business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
Rod 'N' Reel Resort
Don't see what you're looking for?
See all available properties in Royal Oak
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.