Highland Beach Vacation Rentals

Name: A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Address: Rock Hall

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Vacation Rentals in Highland Beach

Caribbean Pool Home <1 mile from Matapeake Beach!

$439

per night

Jun 9 - Jun 10

When you stay at this vacation home in Stevensville, you'll be near the beach and 7 minutes by foot from Matapeake State Park.

Pool

Pet friendly

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

$629

per night

Jun 7 - Jun 8

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 10-minute drive of Sandy Point State Park and Chesapeake Bay Bridge.

Pool

Pet friendly

Historic Annapolis Home!

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay Bridge.

Free WiFi

Outdoor Space

Directly Across from Gate One & Steps from the Waterfront

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 13 minutes from Sandy Point State Park.

Pet friendly

Fireplace

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!

With a stay at this vacation home in Rock Hall, you'll be within a 15-minute walk of Rock Hall Harbor and Waterman’s Museum.

Pet friendly

Free WiFi

Recently Renovated Annapolis Home - Conveniently Located

With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 13 minutes from Sandy Point State Park.

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

With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.

Pet friendly

Free WiFi

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.

Pet friendly

Free WiFi

Pet Friendly - Stone's throw from Annapolis City Dock with private back patio

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 13 minutes from Chesapeake Bay Bridge.

Cozy suite Located in Presidents Hill

$342

per night

Jun 12 - Jun 13

With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

$239

per night

Jun 9 - Jun 10

With a stay at this vacation home, you'll be centrally located in Annapolis, a 3-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

Free WiFi

Air conditioning

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.

Pet friendly

Free WiFi

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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.