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Search results; Over 1,000 places in Chesapeake Beach

Guest favorite
Apartment in North Beach
Bayside Oasis of Southern Maryland
1 king bed
Mar 20 – 25
$126 per night
4.97 out of 5 average rating, 100 reviews
Superhost
Apartment in North Beach
Cheery 1st Level of Beach House -Walk Everywhere!!
5 beds
Mar 19 – 24
$156 per night
4.73 out of 5 average rating, 60 reviews
Guest favorite
Apartment in Port Republic
Serenity Suite on Chesapeake Bay
2 beds
Apr 7 – 12
$110 per night
4.96 out of 5 average rating, 169 reviews
Guest favorite
Apartment in Lexington Park
Adorable Waterfront Apartment Weekend Getaway
1 queen bed
Sep 23 – 28
$90 per night
5.0 out of 5 average rating, 306 reviews
Guest favorite
Apartment in Leonardtown
Stunning Sunsets on Breton Bay, Seaside apartment
1 king bed
Mar 19 – 24
$125 per night
4.98 out of 5 average rating, 118 reviews
Guest favorite
Apartment in Lusby
Courtyard Studio at Bancroft Manor. Cozy Retreat!
1 double bed
Mar 19 – 24
$94 per night
4.98 out of 5 average rating, 97 reviews
Guest favorite
Apartment in Upper Marlboro
Stylish Fun! Game & Theater Room, Gym, Pool
5 beds
Apr 5 – 10
$172 per night
4.98 out of 5 average rating, 55 reviews
Guest favorite
Apartment in Deale
Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
2 beds
Apr 15 – 20
$179 per night
4.91 out of 5 average rating, 614 reviews
Guest favorite
Apartment in Stevensville
Boutique by the Bay
1 queen bed
Mar 19 – 24
$175 per night
4.97 out of 5 average rating, 239 reviews
Apartment in Deale
Chesapeake Bayside Bungalow
4 beds
Mar 19 – 24
$146 per night
4.52 out of 5 average rating, 54 reviews
Guest favorite
Apartment in Church Creek
Church Creek Natures' Rest
1 queen bed
Mar 21 – 26
$115 per night
4.97 out of 5 average rating, 368 reviews
Apartment in Stevensville
Heron Roost
2 beds
May 5 – 10
$195 per night
Guest favorite
Apartment in Solomons
Island Breeze Solomons
1 queen bed
Apr 14 – 19
$135 per night
4.99 out of 5 average rating, 222 reviews
Guest favorite
Apartment in Saint Michaels
Blue Crab Lodge
3 beds
Mar 24 – 29
$239 per night, originally $310
4.95 out of 5 average rating, 21 reviews
Guest favorite
Apartment in Lexington Park
Historic St. Mary's City, MD
2 beds
Apr 1 – 6
$170 per night
4.97 out of 5 average rating, 501 reviews
Superhost
Apartment in Grasonville
Halcyon house. Lovely views on MD eastern shore.
1 king bed
Apr 1 – 6
$180 per night
4.89 out of 5 average rating, 173 reviews
Guest favorite
Apartment in Washington
Luxury escape in DC now with a private Deck!
1 queen bed
Apr 28 – May 3
$249 per night
5.0 out of 5 average rating, 192 reviews
Apartment in Saint Michaels
Unmatched Luxury Living
2 beds
Mar 20 – 25
$305 per night
4.88 out of 5 average rating, 34 reviews