Beachfront vacation rentals in Chesapeake Bay
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Chesapeake Bay
Guests agree: these beachfront homes 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 beachfront rentals
Pet-friendly beachfront home rentals
Cottage in Westover
4.92 out of 5 average rating, 144 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Cottage in Reedville
4.9 out of 5 average rating, 164 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Guest suite in Stevensville
4.97 out of 5 average rating, 145 reviewsKent Island Haven - A Waterfront Getaway
Cabin in Chestertown
4.98 out of 5 average rating, 215 reviewsRivershore Retreat
Cottage in Berlin
4.99 out of 5 average rating, 121 reviewsBayfront Cottage w/ Amazing Views
Cottage in Lower Township
5.0 out of 5 average rating, 150 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 266 reviewsThe Crab House - a Private, Waterfront Guest House
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Beachfront home rentals with a pool
Condo in Ocean City
4.94 out of 5 average rating, 171 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Home in Cobbs Creek
4.9 out of 5 average rating, 119 reviewsMillionaire $ Views No Xtra Charge! Hot Tub! POOL!
Condo in Ocean City
4.96 out of 5 average rating, 101 reviewsOceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Apartment in Virginia Beach
4.91 out of 5 average rating, 233 reviewsVB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Place to stay in Dennis
4.97 out of 5 average rating, 155 reviewsBoutique Suite, at the Palace in the Woods
Home in Kent Narrows
5.0 out of 5 average rating, 280 reviewsChester Riverfront At Kent Narrows
Home in Montross
5.0 out of 5 average rating, 123 reviewsBeach Please! River cottage w/private beach & dock
Condo in Ocean City
4.99 out of 5 average rating, 182 reviewsCozy oceanfront condo with stunning ocean views
Private beachfront home rentals
Home in Heathsville
4.94 out of 5 average rating, 124 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Apartment in Pasadena
4.99 out of 5 average rating, 554 reviewsSea Dreamer aka Phenomenal Hospitality
Apartment in North Beach
4.96 out of 5 average rating, 105 reviewsBayside Oasis of Southern Maryland
Apartment in White Stone
4.91 out of 5 average rating, 100 reviewsThe Fish House
Cottage in Colonial Beach
4.93 out of 5 average rating, 193 reviewsCozy cottage 3 blocks from beach
Home in Virginia Beach
4.9 out of 5 average rating, 211 reviewsQuilted Quarters by the Bay with Private Entrance
Home in Gloucester Courthouse
4.97 out of 5 average rating, 286 reviews"Bee-Z Haven" Waterfront Cottage on the Ware River
Condo in Ocean City
4.99 out of 5 average rating, 103 reviewsBeautiful Renovated Ocean Front Condo 1b/1.5ba
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