What are the top rated Cottage 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 Cottage 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/relax-refresh-renew-waterfront-cottage-near-williamsburg/HA-321334520" class="class="static-page-link"">Relax, Refresh, Renew.Waterfront Cottage.Near Williamsburg</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/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/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/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/HA-121287681" class="class="static-page-link"">St. Michael&#39;s Premier In-Town Rental with heated pool.</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>

How much does it cost to rent a cottage in Chesapeake Bay?

The average cost for a cottage rental in Chesapeake Bay is $315 per night. Inclusiveholidays has a wide list of great cottages near Chesapeake Bay that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Chesapeake Bay that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chesapeake Bay to find one that works for you.

Are there quality cottages in Chesapeake Bay that have indoor swimming pools?

As of 2025, the data from Inclusiveholidays shows that there are Over 714 private swimming pools or cottages with indoor pools in the Chesapeake Bay area along with other great amenities.

Chesapeake Bay Cottage Rentals By Owner

Cottage on a Private Island in the York River

From US $215

10.0 (359 Reviews)

Cottage

Cottage on a Private Island in the York River

Air Conditioner
Parking
Pet Friendly

Chesapeake Bay Cottage Rentals & Holiday Homes

Find the best cottages in Chesapeake Bay - We found 714 exact matches

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