Skip to content

Holiday rentals in Chesapeake Bay

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesapeake Bay

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

"Bee-Z Haven" Waterfront Cottage on the Ware River
SUPERHOST
Entire residential home · 4 guests · 2 beds · 2 bathrooms
"Bee-Z Haven" Waterfront Cottage on the Ware RiverCurious 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.
Adorable Waterfront Apartment Weekend Getaway
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Adorable Waterfront Apartment Weekend GetawayBright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!
The Moore Cottage
SUPERHOST
Entire cottage · 2 guests · 1 bed · 1 bathroom
The Moore CottageThe Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chesapeake Bay holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chesapeake Bay

SUPERHOST
  1. Entire guest house
  2. Lusby
Cozy Lakeside Studio Retreat.
₹6,907 per night
SUPERHOST
  1. Entire cottage
  2. Reedville
Private point on the Bay🌤hammock, hot tub, kayaks❤️
₹15,863 per night
SUPERHOST
  1. Entire cottage
  2. Onancock
Waterfront Boutique Cottage getaway Eastern Shore
₹11,261 per night
  1. Entire cabin
  2. Lusby
2-bedroom lake-house with a magnificent view
₹17,396 per night
SUPERHOST
  1. Entire guest house
  2. Onancock
Private romantic waterfront cottage
₹12,462 per night
SUPERHOST
  1. Entire residential home
  2. White Stone
The Guest House across from Little Bay
₹12,065 per night
SUPERHOST
  1. Entire guest house
  2. Onancock
NEWLY Renovated -- Waterfront Getaway
₹6,982 per night
SUPERHOST
  1. Entire cottage
  2. Westover
Rumbley Cottage on the Tangier Sound
₹19,444 per night
SUPERHOST
  1. Entire residential home
  2. Irvington
Unique+ WFH Ofc+ Print+Hot Tub+ King + 3 levels
₹22,523 per night
SUPERHOST
  1. Entire residential home
  2. Grimstead
Gwynns Island Waterfront Getaway
₹8,612 per night
  1. Entire cottage
  2. Lusby
Chesapeake Bay Cottage
₹12,377 per night
SUPERHOST
  1. Entire cottage
  2. Gwynn
Island Get-A-Way on the Chesapeake Bay with Beach
₹12,012 per night