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Vacation rentals in Chesapeake Bay

Vacation 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.

  • Romantic/Modern Chesapeake Waterfront Suite
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    Romantic/Modern Chesapeake Waterfront Suite

    Gift yourself this private, secluded 2nd floor flat--the best hideaway to rest, bond, restore, create, or work. Deep discounts for longer stays; time & sanitizing between. Breezy, country-like setting provides space to escape city hustle. Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax & recharge with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers or cozy up with books/movies & luxuriate in deep soaking tub or European shower.

    What guests are saying:

    “Shawn's Flat is a wonderful getaway for diving into creative projects while being surrounded by the beauty of Nature. Wake to the view of lovely sunrise and relax on the outdoor swing to listen to birds as the sun sets. The Flat is full of inspiring books and positive messaging to keep creative juices flowing. The tub is a wonderful source of relaxation as well! Even though there is not a full kitchen, there are enough kitchen amenities to keep yourself well fed. Shawn was available for support when needed and otherwise, the Flat felt nice and private.”

  • Chester Riverfront At Kent Narrows
    SUPERHOSTEntire flat · 4 guests · 3 beds · 1 bathroom
    Chester Riverfront At Kent Narrows

    My place is spacious, has great water views and is close to restaurants and dining. You’ll love it because of the bay, hot tub, pool, and outdoors space. My place is good for couples, friends, solo adventurers, and families (with kids).

    What guests are saying:

    “Wow!!! This place is amazing - from the outstanding communication, amenities, and location, this home is a the perfect getaway for a family vacation. Also, the bottle of wine was a wonderful touch. Photos and description are accurate. There are messages/notes on all appliances and tools that were extremely helpful. Property - right on the water with a dock. Great for kids to jump off of and launch the paddle board and kayaks. Sandy area to play and relax. Dock has a picnic table to enjoy a meal on the water. Pool and hot tub overlook the water. Tons of space to run around - bring your vball, badminton, or soccer ball for the kids. Also a fire pit for s’mores! Kitchen- tons of dishes, pans, bakeware, silverware, utensils, cup, blender, crockpot, toaster oven coffee pot and keurig, kettle...everything you need to make a meal for the family. Safeway is an 8 min drive. Royal farms is a 10 min walk or extremely quick bike ride to pick up some groceries. There’s basic slices of salt, pepper, herb seasoning, etc. Bedrooms - extremely clean and beds and bedding were so comfortable. 2nd bedroom has washer and dryer. Lots of storage space for clothing. Living room/dining - tons of seating and very large and comfortable. Extras - corn hole set, 3 adult bicycles (trail is around the corner), kayaks and paddle board, floats for the pool, board games, lounge chairs and hammock, Bluetooth speaker to bring outdoors, collapsible chairs for the fire pit, shampoo conditioner combo and body wash in the bathroom. Everyone you need For a relaxing family vacation is in this home.”

  • Chesapeake Bay Cottage
    SUPERHOSTEntire cottage · 4 guests · 2 beds · 1 bathroom
    Chesapeake Bay Cottage

    Cottage by the Bay. Escape the hustle & bustle for a nature reprieve. Sip wine on the porch, bird-watching sunroom, & roast marsh mellows. Dog friendly! Walk, fish, & kayak the beach! Hike the parks! Hunt for fossils & sharks teeth! Visit Solomon's Island!

    What guests are saying:

    “Hannah is seriously the best host. This is the second year dealing with Hannah while staying in the area for work. And I will continue to do so! Even planning on a trip outside of work to stay in area and Intend on booking with Hannah! The cottage is cute and quaint. Simply perfect for my month stay! It has everything needed for short and long term stays minus the food (of course!) The beach is just down the hill and the views are priceless! There are extra games and books for downtime (if you have any!) Word of note there is no TV, but this place isn’t meant for staying in and binge watching tv! The sunroom is perfect for morning! Great to sit and relax and sip on coffee! And there’s a fire ring outback! Perfect for nice evenings! Hannah is great on checking in and she will make sure everything is right on the drop of a dime! The cottage was clean and so refreshing! Look forward to staying again!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
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  • 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

The Laughing King Retreat Honeymoon Island Cottage
SUPERHOSTTiny house
The Laughing King Retreat Honeymoon Island Cottage
Price:€132 / night
Ocean Park Cottage - Garden by Bay
SUPERHOSTEntire cottage
Ocean Park Cottage - Garden by Bay
Price:€60 / night
Beach Cottage Sand Suite
Entire flat
Beach Cottage Sand Suite
Price:€66 / night
The Studio at Holly Cove-Waterfront
SUPERHOSTEntire guest house
The Studio at Holly Cove-Waterfront
Price:€84 / night
Franktown Artist Cottage
SUPERHOSTEntire guest house
Franktown Artist Cottage
Price:€70 / night
Dolphin Run - 2 Blocks From Beach - Spacious Home
SUPERHOSTEntire house
Dolphin Run - 2 Blocks From Beach - Spacious Home
Price:€70 / night
Wiseacre MidCentury Lake Estate: Near Beach & Bay
SUPERHOSTPrivate room
Wiseacre MidCentury Lake Estate: Near Beach & Bay
Price:€181 / night
Perfect St. Michaels Getaway
SUPERHOSTEntire cottage
Perfect St. Michaels Getaway
Price:€156 / night
Beach Front Property (steps from the sand)
SUPERHOSTEntire flat
Beach Front Property (steps from the sand)
Price:€88 / night
Guest House! 4 Minute Walk To Willoughby Beach!
SUPERHOSTEntire guest house
Guest House! 4 Minute Walk To Willoughby Beach!
Price:€76 / night
Cottage at Calvert Cliffs, near water & Solomon’s.
SUPERHOSTEntire house
Cottage at Calvert Cliffs, near water & Solomon’s.
Price:€133 / night
Virginia Beach 2 King BR apt 100 feet from beach
SUPERHOSTEntire guest suite
Virginia Beach 2 King BR apt 100 feet from beach
Price:€115 / night
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