Chesapeake Bay vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Chesapeake Bay
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Home in Gloucester Courthouse
"Bee-Z Haven" Waterfront Cottage on the Ware River
Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.
$180 per night
SUPERHOST
Cottage in White Stone
Modern Island Cottage
Tucked away on Fleets Island, this modern cottage offers the privacy of over 7 wooded acres on Little Oyster Creek with kayaks you can use to easily access the River and Bay. The main house is newly-built with great light, ping-pong, two bedrooms with Queen beds, two baths, cozy loft with TV, gas fireplace, stylish kitchen, and a sprawling deck for relaxing among the trees. Through the woods you'll find the secluded Treehouse and Dock for planning and launching your kayak adventures.
$245 per night
SUPERHOST
Cottage in Onancock
Waterfront Boutique Cottage getaway Eastern Shore
A perfect little waterfront getaway at the newly renovated Westview Cottage on Onancock Creek. Wake up to a beautiful water views through floor to ceiling glass doors. Your own private, peaceful escape in the country conveniently located approx 10 minutes from downtown historic Onancock. This upscale cottage is surrounded by fields and water and has a deck on the back and an indoor and outdoor shower. Surround yourself in the peaceful luxury of our beautiful Eastern Shore
$165 per night
Vacation rentals for every style
Get the amount of space that is right for you
