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
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Popular amenities for Chesapeake Bay beachfront rentals
Pet-friendly beachfront home rentals
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Oct 20 – 27
Cabin in Chestertown
4.98 out of 5 average rating, 215 reviewsRivershore Retreat
Oct 16 – 23
Cottage in Norfolk
4.99 out of 5 average rating, 268 reviewsLovely Ocean View Cottage
Nov 21 – 28
Guest suite in Stevensville
4.97 out of 5 average rating, 145 reviewsKent Island Haven - A Waterfront Getaway
Dec 19 – 26
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Nov 11 – 18
Cottage in Lower Township
5.0 out of 5 average rating, 146 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Mar 26 – Apr 2
Home in Milton
4.99 out of 5 average rating, 190 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Mar 7 – 14
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
May 30 – Jun 6
Beachfront home rentals with a pool
Home in Cobbs Creek
4.9 out of 5 average rating, 118 reviewsMillionaire $ Views No Xtra Charge! Hot Tub! POOL!
Feb 12 – 19
Condo in Ocean City
4.94 out of 5 average rating, 169 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Dec 16 – 23
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Apartment in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
Aug 20 – 27
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Mar 30 – Apr 6
Apartment in Virginia Beach
4.91 out of 5 average rating, 232 reviewsVB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Feb 12 – 19
Home in Montross
5.0 out of 5 average rating, 122 reviewsBeach Please! River cottage w/private beach & dock
Nov 7 – 14
Place to stay in Dennis
4.97 out of 5 average rating, 153 reviewsBoutique Suite, at the Palace in the Woods
Mar 22 – 29
Private beachfront home rentals
Guest suite in Tilghman Island
4.96 out of 5 average rating, 114 reviewsBlack Walnut Cove Retreat, Tilghman Island
Jul 29 – Aug 5
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
Jan 11 – 18
Apartment in Pasadena
4.99 out of 5 average rating, 550 reviewsSea Dreamer aka Phenomenal Hospitality
Nov 7 – 14
Condo in Ocean City
4.99 out of 5 average rating, 101 reviewsBeautiful Renovated Ocean Front Condo 1b/1.5ba
Mar 5 – 12
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Nov 11 – 18
Home in Virginia Beach
4.9 out of 5 average rating, 209 reviewsQuilted Quarters by the Bay with Private Entrance
Dec 4 – 11
Apartment in North Beach
4.96 out of 5 average rating, 104 reviewsBayside Oasis of Southern Maryland
Dec 7 – 14
Cottage in Urbanna
4.99 out of 5 average rating, 134 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Oct 25 – Nov 1
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