Beachfront vacation rentals in Chesapeake Bay
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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 Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Jan. 23 – 30
Cottage in Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Feb. 23 – Mar. 2
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
Mar. 24 – 31
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Feb. 3 – 10
Guest suite in Stevensville
4.97 out of 5 average rating, 145 reviewsKent Island Haven - A Waterfront Getaway
Jan. 1 – 8
Cottage in Lower Township
5.0 out of 5 average rating, 146 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Oct. 4 – 11
Home in Tracys Landing
4.99 out of 5 average rating, 166 reviewsThe Little Gypsy BoHome
Dec. 16 – 23
Beachfront home rentals with a pool
Condo in Ocean City
4.94 out of 5 average rating, 169 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Feb. 1 – 8
Home in Ocean City
4.94 out of 5 average rating, 221 reviewsMad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Jan. 22 – 29
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
Nov. 2 – 9
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Mar. 15 – 22
Apartment in Virginia Beach
4.91 out of 5 average rating, 232 reviewsVB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Feb. 4 – 11
Apartment in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
Jan. 18 – 25
Home in Montross
5.0 out of 5 average rating, 122 reviewsBeach Please! River cottage w/private beach & dock
Dec. 19 – 26
Home in Cobbs Creek
4.9 out of 5 average rating, 118 reviewsMillionaire $ Views No Xtra Charge! Hot Tub! POOL!
Dec. 15 – 22
Private beachfront home rentals
Apartment in Pasadena
4.99 out of 5 average rating, 550 reviewsSea Dreamer aka Phenomenal Hospitality
Apr. 9 – 16
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
Mar. 21 – 28
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Mar. 28 – Apr. 4
Apartment in North Beach
4.96 out of 5 average rating, 104 reviewsBayside Oasis of Southern Maryland
Nov. 26 – Dec. 3
Home in Gloucester Courthouse
4.97 out of 5 average rating, 284 reviews"Bee-Z Haven" Waterfront Cottage on the Ware River
Apr. 1 – 8
Barn in Selbyville
5.0 out of 5 average rating, 149 reviewsRanch Stay- Farm Animals, Jacuzzi, Arcade, Beaches
Nov. 6 – 13
Cottage in Urbanna
4.99 out of 5 average rating, 134 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Oct. 18 – 25
Home in Virginia Beach
4.9 out of 5 average rating, 209 reviewsQuilted Quarters by the Bay with Private Entrance
Dec. 1 – 8
Destinations to explore
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