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
Dec 20 – 27
Cottage in Reedville
4.9 out of 5 average rating, 162 reviewsPrivate point on the Bay🌤hammock, hot tub, kayaks❤️
Apr 10 – 17
Cabin in Chestertown
4.98 out of 5 average rating, 215 reviewsRivershore Retreat
Sep 28 – Oct 5
Cottage in Norfolk
4.99 out of 5 average rating, 268 reviewsLovely Ocean View Cottage
Apr 11 – 18
Cottage in Lower Township
5.0 out of 5 average rating, 146 reviewsOctopus Cottage: Hot Tub | Kayaks | Fire Pit
Mar 4 – 11
Home in Shady Side
5.0 out of 5 average rating, 118 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Jan 18 – 25
Guest suite in Stevensville
4.97 out of 5 average rating, 145 reviewsKent Island Haven - A Waterfront Getaway
Nov 12 – 19
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 263 reviewsThe Crab House - a Private, Waterfront Guest House
Oct 16 – 23
Beachfront home rentals with a pool
Home in Cobbs Creek
4.9 out of 5 average rating, 117 reviewsMillionaire $ Views No Xtra Charge! Hot Tub! POOL!
Apr 2 – 9
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Condo in Ocean City
4.94 out of 5 average rating, 169 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Nov 30 – Dec 7
Cottage in Norfolk
4.97 out of 5 average rating, 202 reviewsPositano Villa
Mar 27 – Apr 3
Apartment in Cape Charles
4.98 out of 5 average rating, 183 reviewsCape Charles Plantation Home “Nevill’s Nook Suite”
Dec 9 – 16
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
Dec 4 – 11
Place to stay in Dennis
4.97 out of 5 average rating, 153 reviewsBoutique Suite, at the Palace in the Woods
Apr 1 – 8
Condo in Ocean City
4.91 out of 5 average rating, 257 reviewsOcean Front 802 Midtown Oasis Pool & Parking
Jan 12 – 19
Private beachfront home rentals
Apartment in Pasadena
4.99 out of 5 average rating, 550 reviewsSea Dreamer aka Phenomenal Hospitality
Feb 23 – Mar 2
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Sep 22 – 29
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
Jan 4 – 11
Apartment in North Beach
4.96 out of 5 average rating, 103 reviewsBayside Oasis of Southern Maryland
Oct 21 – 28
Tiny home in Selbyville
4.98 out of 5 average rating, 213 reviewsDestination Location! Farm Animals, Tours, Beaches
Nov 8 – 15
Home in Virginia Beach
4.9 out of 5 average rating, 207 reviewsQuilted Quarters by the Bay with Private Entrance
Nov 30 – Dec 7
Home in Lexington Park
4.96 out of 5 average rating, 140 reviewsPrivate beach retreat in historic St. Mary's City
Mar 23 – 30
Home in Gloucester Courthouse
4.97 out of 5 average rating, 284 reviews"Bee-Z Haven" Waterfront Cottage on the Ware River
Apr 28 – May 5
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