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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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake Bay vacation rentals
Chesapeake Bay waterfront vacation rentals
![](https://a0.muscache.com/im/pictures/f86aaabb-d8b4-474c-8089-2cd6b5609b6b.jpg?im_w=720)
Guesthouse in White Stone
5 out of 5 average rating, 201 reviewsWaterfront Guesthouse II on the Rappahannock
![](https://a0.muscache.com/im/pictures/miso/Hosting-53447772/original/f58ad369-40df-4a76-be4c-56219bea7ed0.jpeg?im_w=720)
Cottage in Leonardtown
4.96 out of 5 average rating, 144 reviewsBeach Front and 'Perfectly Placed'
![](https://a0.muscache.com/im/pictures/91bb0d73-415d-44f0-bca6-443b10e551b0.jpg?im_w=720)
Cottage in Smith Island
4.97 out of 5 average rating, 202 reviewsLevering Creek Cottage with Private Docking
![](https://a0.muscache.com/im/pictures/381d0c12-87f3-4cc4-8d95-15b638126b38.jpg?im_w=720)
Rental unit in North
4.98 out of 5 average rating, 205 reviewsLittle Cove Cottage, Couples Retreat/Mathews
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Cottage in Urbanna
4.99 out of 5 average rating, 146 reviewsLittle Dipper -private beach,Kayaks & paddleboards
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Guest suite in Colonial Beach
4.97 out of 5 average rating, 286 reviewsBayview Bungalow
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Home in Tracys Landing
4.99 out of 5 average rating, 181 reviewsThe Little Gypsy BoHome
![](https://a0.muscache.com/im/pictures/miso/Hosting-27052675/original/eee7f044-e6eb-42e7-a582-984f71e23add.jpeg?im_w=720)
Guest suite in Piney Point
4.94 out of 5 average rating, 238 reviewsSpectacular beachfront walk-out in Piney Point MD
Chesapeake Bay fishing vacation rentals
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Rental unit in Stevensville
4.98 out of 5 average rating, 256 reviewsBoutique by the Bay
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Tiny home in Cape Charles
4.98 out of 5 average rating, 285 reviewsThe Laughing King Retreat Honeymoon Island Cottage
![](https://a0.muscache.com/im/pictures/miso/Hosting-624477963128435482/original/63f86d4c-d57e-4f80-9139-6601be848c9c.jpeg?im_w=720)
Guesthouse in Church Road
5 out of 5 average rating, 156 reviewsHeron Rock: Lakefront Cottage on Lake Chesdin
![](https://a0.muscache.com/im/pictures/miso/Hosting-25191088/original/b767057d-78f4-41f4-8c18-7f47d88afafa.jpeg?im_w=720)
Cabin in Lusby
4.92 out of 5 average rating, 224 reviewsPeaceful Waterfront Retreat on The Bay
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Rental unit in Frederica
4.96 out of 5 average rating, 270 reviewsSmokefree Lakeside Relaxation
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Cottage in Gloucester Courthouse
4.98 out of 5 average rating, 202 reviewsHistoric Ware River Cottage at Glebefield
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Guest suite in Arnold
4.96 out of 5 average rating, 589 reviewsOld Bay Bungalow
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6Mzg1ODEw/original/2e614deb-5053-43e6-ab48-d7e430975d27.jpeg?im_w=720)
Loft in Cape May Court House
4.97 out of 5 average rating, 598 reviewsQuiet Lakefront Studio - Close to the Beach
Chesapeake Bay house rentals
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Home in North Beach
5 out of 5 average rating, 105 reviewsWaterfront, Dog-friendly, Hot Tub, Peleton, Bikes
![](https://a0.muscache.com/im/pictures/miso/Hosting-34271923/original/9313ad4a-25ea-4bff-9300-8c2352067f00.jpeg?im_w=720)
Home in Annapolis
5 out of 5 average rating, 111 reviewsLuxury Waterfront Annapolis/ Private Beach & Dock
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Home in Lexington Park
4.95 out of 5 average rating, 149 reviewsPrivate beach retreat in historic St. Mary's City
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Home in Annapolis
4.95 out of 5 average rating, 125 reviewsHistoric Downtown in-law suite
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Home in Ocean View
4.91 out of 5 average rating, 547 reviewsTiny House at Good Earth, near Bethany Beach
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Home in Cobbs Creek
4.9 out of 5 average rating, 123 reviewsMillionaire $ Views No Xtra Charge! Hot Tub! POOL!
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Home in Scotland
4.92 out of 5 average rating, 114 reviewsSpacious Gorgeous Waterfront Home with Sunset View
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Home in Lusby
4.99 out of 5 average rating, 271 reviewsCove Point Beach Cabin
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