What are the top rated Villa Rentals in Chesapeake Bay?

There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Chesapeake Bay: <a href="/property/adorable-cottage-in-the-heart-of-the-old-beach-area-close-to-the-boardwalk/HA-1214247297" class="class="static-page-link"">Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.</a> <a href="/property/annapolis-waterfront-tiny-house-in-garden-setting/HA-3211152603" class="class="static-page-link"">Annapolis waterfront &#34;tiny house&#34; in garden setting</a> <a href="/property/the-yellow-cottage-on-harness-creek/HA-321300511" class="class="static-page-link"">The Yellow Cottage on Harness Creek</a> <a href="/property/waterfront-sunset-nature-reserve-kayak-eagle-osprey-snakehead-butterflies/HA-121207415" class="class="static-page-link"">Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies</a> <a href="/property/private-1300-sq-ft-cottage-in-historic-yorktown-w-trolley-access/HA-3211714751" class="class="static-page-link"">Private 1300 sq ft Cottage in Historic Yorktown-w/trolley access</a> <a href="/property/potomac-river-getaway-at-mckays-beach/HA-3211570197" class="class="static-page-link"">Potomac River Getaway at McKays Beach</a> <a href="/property/st-michael-s-premier-in-town-rental-with-heated-pool-pool-opens-4-3/HA-121287681" class="class="static-page-link"">St. Michael&#39;s Premier In-Town Rental with heated pool. Pool opens 4/3</a> <a href="/property/heart-of-williamsburg-guest-house-3-bedrooms-2-full-baths-sleeps-6/HA-1214271061" class="class="static-page-link"">Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6</a> <a href="/property/bay-side-retreat-hays-beach-step-of-your-porch-into-the-sand-chesapeake-bay/HA-3212007626" class="class="static-page-link"">𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘</a> <a href="/property/charming-cottage-ultimate-relaxation-destination/HA-3212228137" class="class="static-page-link"">Charming Cottage - Ultimate Relaxation Destination</a>

What is the rate per night for renting a villa near Chesapeake Bay?

At Piratecovecottages, the average rental fee for standard villas in Chesapeake Bay is $317 per night. Piratecovecottages has a large database of quality villas near Chesapeake Bay that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.

Are there any rental villas in Chesapeake Bay that are suitable for families?

Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Chesapeake Bay to find what works for you.

Do your rental villas in Chesapeake Bay have indoor swimming pools?

Based on the 2026 data from our Piratecovecottages site, there are more than 720 private swimming pools or villas with indoor pools in or near Chesapeake Bay.

Chesapeake Bay Villa Rentals【 LUXURY 】

Cottage on a Private Island in the York River

From US $213

10.0 (359 Reviews)

Cottage

Cottage on a Private Island in the York River

Air Conditioner
Parking
Pet Friendly

Chesapeake Bay Villa Rentals & Homes

Find villas near Chesapeake Bay - We found 720 exact matches

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