Beach house holiday rentals in Chesapeake Beach

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Top-rated beach house rentals in Chesapeake Beach

Guests agree: these beach houses are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Pasadena

5 out of 5 average rating, 28 reviews

Kayak Cove

Visiting the Kayak Cove is all you could want for a relaxing stay. Our cottage is located on a peaceful cove where you can sit back and enjoy the water view, majestic trees and wildlife from your choice of a comfy Adirondack chair around the fire pit on the beautiful paver patio, the hammocks or the brand new dock--bring your fishing rods! And don't forget those kayaks! The cottage itself has been 100% renovated with all new everything. So convenient to anything you need-20 min to BWI airport

Guest favourite

Home in Reedville

4.93 out of 5 average rating, 42 reviews

Summer Breeze waterfront new home-Private Beach

ALMOST FULLY BOOKED FOR SUMMER - RENT NOW! ! Summer Breeze, located on the Chesapeake Bay in the fishing village of Reedville, is our new 3 Bedroom, 2 Bath home with waterfront shoreline and beach on a peaceful cove. The neighborhood beach, which is for residents and guests renting, fronts directly on the Chesapeake Bay and is just a few lots, and a short walk away. The gentle Bay beach with soft sand, gentle waves, and gently sloping bottom are perfect for fun and play for the whole family!

Guest favourite

Home in Annapolis

4.97 out of 5 average rating, 35 reviews

Cheerful Cottage Home in Beach Community

Stay in a historic Bay Ridge cottage home, steps from beaches and a high bluff overlooking the Chesapeake Bay. Enjoy a cozy wood fire, the private back garden with tranquil fish ponds and a sunny deck for dining or lounging. This is our family home, filled with antique and vintage furnishings and original art and craft. We welcome you to grab a book, take a walk in the woods, or picnic on your choice of quiet beach.

Superhost

Home in Reedville

4.87 out of 5 average rating, 153 reviews

Gorgeous Views! 150 ft private beach/Dock/Hot Tub

Come enjoy the breathtaking views and over 3300 square feet of beautifully renovated indoor living space. 800sf Master suite with HUGE water views. Large living/dining area makes this a very comfortable space for 10+ guests. Incredible outdoor space: patio, deck, HUGE screened porch, dock, 150 ft of private beach, boat dock, and hot tub! This place has it all!