Royal Oak Vacation Rentals

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Vacation Rentals in Royal Oak

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach MD

Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.

Kitchen

Air conditioning

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD

$324 nightly

$343 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.

Kitchen

Washer

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD

Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.

Pool

Kitchen

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD

Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park.

Kitchen

Washer

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and 3 minutes by foot from Muskrat Park.

Kitchen

Washer

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick MD

$345 nightly

$366 total

Dec 17 - Dec 18

Total with taxes and fees

With a stay at this vacation home in Prince Frederick, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick MD

$339 nightly

$359 total

Dec 17 - Dec 18

Total with taxes and fees

Located in Prince Frederick, this vacation home is near the beach, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

Tilghman Island MD

With a stay at this vacation home in Tilghman, you'll be within a 5-minute walk of Talbot County Library Tilghman Branch and Tilghman Watermen’s Museum.

Kitchen

Washer

Beautiful 2-bedroom water view house in Annapolis

Annapolis MD

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Washer

Dryer

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Easton MD

With a stay at this vacation home in Easton, you'll be on the beach, and 6.6 mi (10.7 km) from Saint Michaels Village and 7.3 mi (11.7 km) from St. Michaels Winery.

Pool

Hot Tub

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

Tracys Landing MD

This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.

Pool

Hot Tub

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Woolford MD

A stay at this vacation home places you in the heart of Woolford, and within a 15-minute drive of Blackwater National Wildlife Refuge.

Pool

Hot Tub

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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.