Good morning Baltimore! Home of the Baltimore Ravens and the Chesapeake Bay, Maryland is an absolutely gorgeous place to vacation no matter what time of year. Visit some of the most beautiful beaches and breathtaking mountains in the country, or enjoy some live theatre and some o' Maryland's famous blue crabs. Whatever tickles your fancy, RedAwning has the vacation rental for you. Browse your favorite Baltimore region using the blue location links below, or filter your preferences using the panel on the side. With our simplified booking process you'll have the most important part of your trip buttoned in no time.

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  1. $158 to $689/night

    Beachwalk II 12

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
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  3. $327 to $437/night

    Antigua 403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
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  5. $382 to $741/night

    Harbour Island 403M

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
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  7. $192 to $689/night

    Ocean Hideaway 111

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  9. $171 to $445/night

    Barefoot Country 508

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  11. $180 to $274/night

    Jada 4H

    1 Bedroom BathroomSleeps 4
    3 nights minstay
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  13. $158 to $379/night

    Thunder Island 7A

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
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  15. $259 to $471/night

    Gullway Townhouse 2833

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
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  17. $142 to $306/night

    Seascape-Heron Harbour 204-4

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  19. $124 to $324/night

    Beachmark 4K

    1 Bedroom BathroomSleeps 5
    3 nights minstay
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  21. $146 to $518/night

    Sea Watch 1319

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
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  23. $129 to $438/night

    Bimini 107

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
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  25. $191 to $360/night

    Sunstar 3

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
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  27. $113 to $495/night

    Eagle Bay 204

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
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  29. $518 to $1,107/night

    Bel Mare 100

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
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  31. $125 to $296/night

    Barracuda 4

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pets OK
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  33. $126 to $340/night

    Sea Watch 205

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
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  35. $131 to $358/night

    Sea Watch 1417

    2 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
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  37. $144 to $430/night

    Sandy Pause III 802A

    3 BedroomsBathroomsSleeps 10
    7 nights minstay
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  39. $179 to $305/night

    402 Playa Flamingo

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
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  41. $430 to $673/night

    12th Street House up

    5 BedroomsBathroomsSleeps 14
    7 nights minstay
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  43. $113 to $286/night

    Sunset Bay II 512

    2 BedroomsBathroomsSleeps 8
    7 nights minstay
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  45. $126 to $232/night

    Bahama Princess C

    2 BedroomsBathroomsSleeps 7
    7 nights minstay
    Pool
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  47. $282 to $584/night

    Bel Mare 103

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
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  49. $251 to $610/night

    Boards Edge 103

    4 BedroomsBathroomsSleeps 11
    7 nights minstay
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  51. $153 to $377/night

    Runaway Bay II 525

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
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  53. $162 to $422/night

    Atlantis 1810

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
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  55. $556 to $717/night

    Pilot House 3- Incredible Views from this Direct Ocean-F...

    4 BedroomsBathroomsSleeps 12
    7 nights minstay
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  57. $117 to $286/night

    Golden Sands 504

    2 Bedrooms BathroomSleeps 4
    7 nights minstay
    Pool
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  59. $126 to $286/night

    Bimini 305

    2 BedroomsBathroomsSleeps 8
    7 nights minstay
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  61. $108 to $404/night

    Sand Trap 101

    2 BedroomsBathroomsSleeps 8
    7 nights minstay
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  63. $90 to $136/night

    Ocean Waye 216

    Studio BathroomSleeps 4
    7 nights minstay
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  65. $113 to $171/night

    Sea Robin 112

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
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  67. $103 to $199/night

    Skyhaven 303

    1 Bedroom BathroomSleeps 4
    3 nights minstay
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  69. $246 to $268/night

    Constellation House 505

    1 Bedroom BathroomSleeps 4
    3 nights minstay
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  71. $375 to $565/night

    Bella Vista 601- total luxury, 3 bedroom condo, indoor/o...

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
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  73. $214 to $415/night

    Wright View 3

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
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  75. $167 to $251/night

    Sandy Lane Estates B103

    2 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
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  77. $405 to $872/night

    Mariner's Watch 404

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
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  79. $136 to $286/night

    El Marlyn 3

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
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  81. $179 to $382/night

    Thunder Island 64B

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  83. $139 to $269/night

    Fountainhead Towers 909

    2 Bedrooms BathroomSleeps 5
    7 nights minstay
    Pool
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  85. $112 to $224/night

    Assateague Pointe-Windlass Way 12401-56

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
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  87. $248 to $456/night

    New Listing! Seaside Village Gem w/ Balcony & Pool

    3 Bedrooms3.5 BathroomsSleeps 9
    3 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $110 to $316/night

    New Listing! Tasteful Condo: 2 Blocks to Boardwalk

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  91. $356 to $442/night

    New Listing! Upscale Condo w/ Pool, Near Beach

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
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  93. $134 to $398/night

    Tranquil Canal-Front Getaway- 3 Blocks to Beach

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
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  95. $125 to $400/night

    New Listing! Stylish Retreat w/ Pool- Near Beach

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  97. $139 to $422/night

    Sandy Pause Station- brand new for 2020- just steps to t...

    3 BedroomsBathroomsSleeps 10
    7 nights minstay
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  99. $269 to $719/night

    New Listing! Canalfront All-Suite: Steps to Beach

    5 Bedrooms5.5 BathroomsSleeps 12
    3 nights minstay
    FREE CANCELLATION
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  101. $141 to $270/night

    46th St Windjammer 207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pets OK
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $75 to $470/night

    New Listing! Chic Condo w/ Pool & Walkable Locale

    2 Bedrooms BathroomSleeps 5
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  105. $114 to $309/night

    New Listing! Choice Getaway- 5 Pools & Beach Club

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $99 to $188/night

    Assateague Pointe 428

    2 Bedrooms BathroomSleeps 6
    7 nights minstay
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  109. $135 to $319/night

    Worcester House 503

    1 Bedroom BathroomSleeps 6
    2 nights minstay
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  111. $99 to $207/night

    Bayshore Estates 205

    2 Bedrooms BathroomSleeps 6
    7 nights minstay
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  113. $544 to $960/night

    Beautiful Private Summerfield Estate awaits your stay!

    5 Bedrooms3.5 BathroomsSleeps 12
    1 night minstay
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $243 to $809/night

    Laguna Vista 109

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
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  117. $125 to $296/night

    Barracuda 3

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pets OK
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $146 to $358/night

    Thunder Island 67B

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  121. $103 to $266/night

    Frogs F1

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pets OK
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $113 to $323/night

    Jamaican Sun 104

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  125. $182 to $399/night

    Gullway Townhouse 2834

    3 Bedrooms BathroomSleeps 8
    3 nights minstay
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  127. $426 to $501/night

    Breakaway East 310

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $158 to $331/night

    Fantasea 3W

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
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  131. $158 to $266/night

    Sea Point 3

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pets OK
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $112 to $399/night

    English Towers 506

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  135. $142 to $319/night

    Seascape-Heron Harbour 206-10

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $583 to $1,436/night

    Harbour Island 68J

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
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  139. $113 to $423/night

    Century I 702

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
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  141. $174 to $510/night

    Diamond Beach 403

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
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  143. $156 to $396/night

    Thunder Island 157D

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
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  145. $208 to $306/night

    Surf Crest 101

    1 Bedroom BathroomSleeps 6
    3 nights minstay
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $147 to $583/night

    Crab Harbour 4

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $158 to $264/night

    Jockey Beach 342

    1 Bedroom BathroomSleeps 6
    2 nights minstay
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  151. $158 to $370/night

    Thunder Island 159D

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $113 to $278/night

    Our Place At The Beach 105E

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
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  155. $527 to $1,212/night

    Harbour Island 207K

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $135 to $318/night

    Thunder Island 80B

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $162 to $467/night

    102 10th Street A- just gorgeous! Downtown OC townhouse,...

    3 BedroomsBathroomsSleeps 8
    7 nights minstay
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $158 to $332/night

    Bay Cove 3

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $171 to $583/night

    Ocean Hideaway 202

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $348 to $1,347/night

    Harbour Island 79J

    3 BedroomsBathroomsSleeps 12
    3 nights minstay
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $147 to $344/night

    Thunder Island 132C

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $103 to $266/night

    Wight Bay 460

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $125 to $440/night

    New Listing! Whispering Sands Gem w/ Pool & Beach

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $148 to $305/night

    Breakaway East 212

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $225 to $758/night

    Belmont Towers TH 9 (Side)

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $225 to $758/night

    Belmont Towers TH 7 (Side)

    3 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $113 to $278/night

    103 79th Street

    3 BedroomsBathroomsSleeps 9
    3 nights minstay
    Pets OK
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $158 to $502/night

    Silver Moon 403

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $113 to $358/night

    Sunrise Sea 308

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $138 to $347/night

    Marigot Beach 407

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $203 to $411/night

    Our Place At The Beach 103B

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $279 to $493/night

    PYRAMID 19-J

    1 Bedroom1.5  BathroomSleeps 6
    2 nights minstay
    Pool
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $182 to $713/night

    Ocean Palms 103

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $122 to $284/night

    BRADLEY ON THE BAY 132-G

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $135 to $398/night

    Marigot Beach 605

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $199 to $636/night

    SUNSET ISLAND 3-A

    Multiple Units Available
    2 nights minstay
    Pool
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $199 to $598/night

    SEA WATCH 614

    Multiple Units Available
    2 nights minstay
    Pool
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations