Royal Oak Vacations from $374

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Your Royal Oak Vacation

Reserve a Royal Oak vacation package that has everything you need and no unnecessary extras. Good for bars and pubs, culture and cafes, think about basing yourself in the neighborhood of Downtown Cambridge. You'll want to take in the sights during your trip to Royal Oak. Make time for famous attractions like St. Michaels Winery, Chesapeake Bay Maritime Museum and Oxford Museum. A couple of quick clicks is all it takes to create your ideal Royal Oak vacation on Expedia.

The Latest Royal Oak vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
Price was $452, price is now $374 per person
$374
per person
Nov 15 - Nov 18
found 14 hours ago
Roundtrip flight included
Rochester (ROC) to Salisbury (SBY)
8.8/10 Excellent! (1,001 reviews)
Staff is a 10! Room was quite comfortable and clean.

Reviewed on Sep 24, 2025

Americana Princess Suites and Condos

Americana Princess Suites and Condos

2.5 out of 5
Downtown Ocean City
Price was $1,586, price is now $1,206 per person
$1,206
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.2/10 Good! (15 reviews)
This is a decent place to stay. Very walkable. Condo is a nice size! Plenty of room for 2 families of 3. Had a plumbing issue and the staff addressed it very quickly! Would stay here again.

Reviewed on Jun 8, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,425, price is now $1,952 per person
$1,952
per person
Dec 15 - Dec 18
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7.6/10 Good! (87 reviews)
There was a funny smell in the hallway many times throughout the days. Bed was not in good shape

Reviewed on Aug 25, 2025

Atlantic Oceanside Dewey

Atlantic Oceanside Dewey

2.5 out of 5
Price was $806, price is now $672 per person
$672
per person
Nov 15 - Nov 18
found 14 hours ago
Roundtrip flight included
Rochester (ROC) to Salisbury (SBY)
8/10 Very Good! (949 reviews)
Coffee mill atmosphere was nice, very pet friendly, could use work around the edges (rust in the stairwell, outdated and crusty bathtub, stains on the ceiling— things were clean but not nice looking if that makes sense), staff was AMAZING and so helpful. Got into our room early, helped with my service dog not being a pet, got us a parking pass to go to the beach while our room wasn’t ready yet.

Reviewed on Sep 21, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,175, price is now $990 per person
$990
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.2/10 Very Good! (38 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

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Royal Oak Hotel Deals

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak
10/10 Exceptional! (68 reviews)
"This is a beautiful property with great amenities. A very comfortable, spacious house with nice views of the water. The house was clean and ready for us upon arrival. Communication with the host for Q&A was excellent. He responded quickly to our questions. We hope to come back again."

Reviewed on Sep 24, 2025

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Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$92 nightly
The price is $102 total per night from Oct 19 to Oct 20
$102 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"Our room was clean but dated. The water had a bad smell to it."

Reviewed on Sep 30, 2025

St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $265 total per night from Oct 5 to Oct 6
$265 total
Oct 5 - Oct 6
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
"Indoor and outdoor pools were very clean and nice"

Reviewed on Sep 28, 2025

Hyatt Regency Chesapeake Bay
See all 643 properties in Royal Oak
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 Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
St. Michaels Winery, Avalon Theatre and Bill Burton Fishing Pier State Park

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Frequently asked questions

How much does a Royal Oak vacation package cost?
You can pick up a vacation package to this destination from $374 on Expedia. But how much your vacation to Royal Oak costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Royal Oak?
November, December and January are the best times to look for cheap Royal Oak vacation packages. Traveling in less busy periods means you can generally find lower prices on flights and hotels.
How many days is enough for Royal Oak?
Usually, a handful of days is enough to see the major sights during your Royal Oak vacation. However, if you prefer to have some time to unwind or take day trips, think about extending your trip.
How to find the best Royal Oak package deals?
Use Expedia's filter tool to help you find some fabulous Royal Oak package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Royal Oak package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Royal Oak vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights separately. Better still, you can personalize your Royal Oak trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Royal Oak?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Royal Oak escape.
Does Expedia offer Book Now, Pay Later Royal Oak vacation packages?
Jet off on your dream escape to Royal Oak with our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stick to your budget and snap up bargains while they last.

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Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.