Beach house vacation rentals in Chesapeake Beach
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Top-rated beach house rentals in Chesapeake Beach
Guests agree: these beach houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chesapeake Beach beach house rentals
Beachfront house rentals
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 Lusby
4.94 out of 5 average rating, 157 reviewsWaterfront Home on the Chesapeake Bay-Pvt Beach
Apr. 22 – 29
Home in Heathsville
4.93 out of 5 average rating, 122 reviewsWater ft Chesapeake Bay DREaM Vacation Dock Kayaks
Feb. 16 – 23
Home in Cambridge
4.95 out of 5 average rating, 101 reviewsPeaceful Historic House Near Water, with Hot Tub!
Jan. 16 – 23
Home in Colonial Beach
4.93 out of 5 average rating, 115 reviews‘Pipe Dream’ - 3BD/2.5BTH - Awesome water view!
Oct. 8 – 15
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov. 20 – 27
Home in Newburg
4.92 out of 5 average rating, 104 reviewsThe River House, a Wicomico Beach Retreat
Feb. 8 – 15
Beach house rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Dec. 25 – Jan. 1
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec. 4 – 11
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Sep. 16 – 23
Home in Edgewater
4.97 out of 5 average rating, 30 reviewsEntire Beach House with Pool and Hot Tub
Oct. 31 – Nov. 7
Home in Bozman
5.0 out of 5 average rating, 7 reviewsGrace Creek Cottage
Jan. 16 – 23
Home in Sherwood
5.0 out of 5 average rating, 51 reviewsChesapeake Mansion-heated pool 30acre waterfront
Jan. 15 – 22
Home in Annapolis
4.95 out of 5 average rating, 41 reviewsNaptown Suite
Jun. 30 – Jul. 7
Home in Cambridge
4.96 out of 5 average rating, 98 reviewsWaterfront, Fabulous Home for Families with Pool!
Jan. 16 – 23
Private beach house rentals
Home in North Beach
4.91 out of 5 average rating, 23 reviewsLarge Bungalow 2 Blocks to Beach
Aug. 31 – Sep. 7
Home in North Beach
5.0 out of 5 average rating, 95 reviewsWaterfront, Dog-friendly, Hot Tub, Peleton, Bikes
Dec. 31 – Jan. 7
Home in North Beach
4.98 out of 5 average rating, 52 reviewsThe North Beach Retreat House
Oct. 21 – 28
Home in North Beach
4.88 out of 5 average rating, 8 reviewsCute home 3 beds 2 baths!
Jan. 24 – 31
Home in Shady Side
4.97 out of 5 average rating, 66 reviewsCanary Pointe-A popular getaway for 2!
Apr. 16 – 23
Home in North Beach
5.0 out of 5 average rating, 8 reviewsOsprey's Perch
Nov. 16 – 23
Home in North Beach
4.95 out of 5 average rating, 41 reviewsChesapeake Bay, Maryland, Beach Front Paradise
Apr. 16 – 23
Home in North Beach
5.0 out of 5 average rating, 16 reviewsSweet Bamboo
Nov. 12 – 19
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