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 Westover
4.92 out of 5 average rating, 142 reviewsHeaven on the Bay - A Peaceful Waterfront Retreat
Apr 27 – May 4
Guest suite in Stevensville
4.97 out of 5 average rating, 145 reviewsKent Island Haven - A Waterfront Getaway
Dec 9 – 16
Cabin in Chestertown
4.98 out of 5 average rating, 215 reviewsRivershore Retreat
Oct 16 – 23
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Dec 28 – Jan 4
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 264 reviewsThe Crab House - a Private, Waterfront Guest House
Apr 7 – 14
Cottage in Norfolk
4.98 out of 5 average rating, 269 reviewsLovely Ocean View Cottage
Apr 14 – 21
Home in Shady Side
5.0 out of 5 average rating, 119 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Apr 28 – May 5
Home in Milton
4.99 out of 5 average rating, 191 reviewsON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Feb 6 – 13
Beachfront home rentals with a pool
Condo in Ocean City
4.97 out of 5 average rating, 227 reviewsDirect Oceanfront with a View and Amenities Galore
Nov 8 – 15
Home in Cobbs Creek
4.9 out of 5 average rating, 118 reviewsMillionaire $ Views No Xtra Charge! Hot Tub! POOL!
Jan 14 – 21
Home in Kent Narrows
5.0 out of 5 average rating, 280 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Cottage in Berlin
4.99 out of 5 average rating, 121 reviewsBayfront Cottage w/ Amazing Views
Mar 25 – Apr 1
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Feb 6 – 13
Apartment in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
Dec 22 – 29
Home in Montross
5.0 out of 5 average rating, 122 reviewsBeach Please! River cottage w/private beach & dock
Nov 7 – 14
Apartment in Virginia Beach
4.91 out of 5 average rating, 232 reviewsVB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Jan 7 – 14
Private beachfront home rentals
Apartment in Pasadena
4.99 out of 5 average rating, 550 reviewsSea Dreamer aka Phenomenal Hospitality
Oct 30 – Nov 6
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
Dec 7 – 14
Tiny home in Selbyville
4.98 out of 5 average rating, 214 reviewsDestination Location! Farm Animals, Tours, Beaches
Oct 25 – Nov 1
Apartment in North Beach
4.96 out of 5 average rating, 104 reviewsBayside Oasis of Southern Maryland
Apr 22 – 29
Home in Virginia Beach
4.9 out of 5 average rating, 209 reviewsQuilted Quarters by the Bay with Private Entrance
Jan 23 – 30
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Jul 21 – 28
Cottage in Urbanna
4.99 out of 5 average rating, 135 reviewsLittle Dipper -private beach,Kayaks & paddleboards
Oct 23 – 30
Home in Gloucester Courthouse
4.97 out of 5 average rating, 285 reviews"Bee-Z Haven" Waterfront Cottage on the Ware River
Dec 15 – 22
Destinations to explore
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