Beachfront vacation rentals in Chesapeake Beach
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Top-rated beachfront rentals in Chesapeake Beach
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 Beach beachfront rentals
Pet-friendly beachfront home rentals
Guest suite in Dunnsville
5.0 out of 5 average rating, 239 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Oct. 24 – 31
Home in Grasonville
4.94 out of 5 average rating, 226 reviewsRiver Front, Private Single Family Home
Nov. 17 – 24
Home in Cambridge
4.9 out of 5 average rating, 146 reviewsJewell on the Chesapeake
Jul. 28 – Aug. 4
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 264 reviewsThe Crab House - a Private, Waterfront Guest House
Oct. 16 – 23
Apartment in Cambridge
4.92 out of 5 average rating, 101 reviewsLittle Slice of Cambridge. Newly listed, 2 bedroom
Aug. 8 – 15
Guest suite in Piney Point
4.94 out of 5 average rating, 225 reviewsSpectacular beachfront walk-out in Piney Point MD
Mar. 27 – Apr. 3
Cottage in Westover
4.99 out of 5 average rating, 182 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Feb. 24 – Mar. 3
Home in Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
Apr. 22 – 29
Beachfront home rentals with a pool
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
Nov. 2 – 9
Home in Montross
5.0 out of 5 average rating, 121 reviewsBeach Please! River cottage w/private beach & dock
Dec. 4 – 11
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov. 20 – 27
Guesthouse in Queenstown
4.9 out of 5 average rating, 21 reviewsWaterfront Getaway
Nov. 9 – 16
Cottage in Neavitt
4.69 out of 5 average rating, 16 reviewsGrandview - Cottage 1A, King Bed, Pool, Bay, WIFI
Jan. 14 – 21
Home in Montross
5.0 out of 5 average rating, 48 reviewsWaterfront+Kayaks+Gameroom+Pool+Firepit+EV/Dog OK
Sep. 23 – 30
Home in Edgewater
4.97 out of 5 average rating, 31 reviewsWaterfront | Pool | Hot tub | Beach Access
May 27 – Jun. 3
Villa in Hague
4.96 out of 5 average rating, 27 reviewsSea Glass Paradise
Apr. 6 – 13
Private beachfront home rentals
Apartment in Pasadena
4.99 out of 5 average rating, 550 reviewsSea Dreamer aka Phenomenal Hospitality
Feb. 23 – Mar. 2
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
Dec. 10 – 17
Cottage in North Beach
4.86 out of 5 average rating, 171 reviewsFull house rental in Twin Beach. 1 bk from the Bay
Feb. 7 – 14
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 Annapolis
4.99 out of 5 average rating, 199 reviewsCape St Claire waterfront getaway
Aug. 1 – 8
Cabin in Reedville
4.97 out of 5 average rating, 190 reviewsDinna Fash-3 BR Waterfront Log Cabin
Feb. 21 – 28
Home in St. Leonard
4.91 out of 5 average rating, 162 reviewsCozy Cottage on the Chesapeake Bay
Oct. 21 – 28
Home in Colonial Beach
4.84 out of 5 average rating, 128 reviews*WATERFRONT BEACH HOUSE PARADISE*
Aug. 16 – 23
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