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. $181 to $671/night

    Delightful Pet Friendly Family Home In Great Location

    4 BedroomsBathroomsSleeps 9
    1 night minstay
    Pets OK
    FREE CANCELLATION
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  3. $191 to $282/night

    The Lodge at Wisp-One-BDRM Apartment Sleeps 6

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
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  5. $118 to $558/night

    Bay Princess 211

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
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  7. $163 to $554/night

    Ocean Hideaway 202

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  9. $194 to $383/night

    Ocean Pines-Moonraker Road 54

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pets OK
    FREE CANCELLATION
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  11. $184 to $377/night

    Thunder Island 147D

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  13. $204 to $661/night

    Avalon 507

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
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  15. $155 to $615/night

    Dune Mist III 1S

    3 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pets OK
    FREE CANCELLATION
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  17. $109 to $554/night

    Eagle Bay 204

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  19. $175 to $434/night

    Alameda 6- Ocean City, MD

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $175 to $388/night

    Baltimore's Best Home Away From Home

    2 BedroomsBathroomsSleeps 4
    1 night minstay
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $129 to $320/night

    Inner Harbor's Best Furnished Luxury Apartments

    1 Bedroom BathroomSleeps 2
    1 night minstay
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $128 to $301/night

    Fountainhead 209

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  27. $90 to $267/night

    103 79th Street

    3 BedroomsBathroomsSleeps 9
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $405 to $788/night

    Harbour Island 403M

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  31. $173 to $434/night

    Barefoot Country 508

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  33. $155 to $288/night

    Jada 4H- Ocean City, MD

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  35. $136 to $336/night

    Seascape-Heron Harbour 204-4

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  37. $133 to $408/night

    Sea Watch 1319

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
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  39. $146 to $314/night

    Seascape Heron Harbour

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  41. $99 to $247/night

    Breakaway East 109

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  43. $140 to $746/night

    Harbour Island 302L

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  45. $99 to $297/night

    Wight Bay 460

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  47. $182 to $723/night

    Harbour Island 102M

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $470 to $1,004/night

    Bel Mare 100

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    FREE CANCELLATION
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  51. $346 to $1,340/night

    Harbour Island 79J

    3 BedroomsBathroomsSleeps 12
    3 nights minstay
    FREE CANCELLATION
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  53. $169 to $639/night

    Crab Harbour 4

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
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  55. $224 to $833/night

    Harbour Island 303L

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  57. $109 to $265/night

    Our Place At The Beach 105E

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  59. $130 to $304/night

    Thunder Island 80B

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $140 to $354/night

    Thunder Island 132C

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  63. $127 to $343/night

    Surf Crest 103

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  65. $374 to $851/night

    Harbour Island 106L

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $161 to $401/night

    Thunder Island 109C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  69. $99 to $279/night

    Barefoot Country 304

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  71. $329 to $987/night

    Bahia Vista I 508

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $291 to $1,025/night

    Sunset Island- Beach Side Drive 24

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool
    FREE CANCELLATION
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  75. $388 to $661/night

    Sungate 401

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $170 to $382/night

    Thunder Island 16A

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $127 to $274/night

    Raffles 206

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  81. $184 to $524/night

    Marigot Beach 705

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $175 to $434/night

    Gullway Townhouse 2823

    3 Bedrooms BathroomSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  85. $115 to $308/night

    Seascape-Heron Harbour 202-3

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $232 to $1,102/night

    Harbour Island 401M

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $127 to $308/night

    Beachaven 305

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $78 to $239/night

    Marshall Inn 314

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $78 to $239/night

    Marshall Inn 303

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $184 to $780/night

    Montego Bay-106 Sea Lane

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $348 to $917/night

    Bella Mar C

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $176 to $316/night

    Beachmark 3D

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  101. $243 to $444/night

    Surfwood 203

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  103. $368 to $838/night

    Mariner's Watch 404

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    FREE CANCELLATION
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  105. $130 to $304/night

    Worcester House 503

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  107. $109 to $340/night

    Sunrise Sea 308

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $146 to $365/night

    Marigot Beach 407

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $109 to $434/night

    Century I 702

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $268 to $838/night

    Ocean Hideaway 111

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $230 to $434/night

    Bonaire 404

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $170 to $624/night

    High Point South 1C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $204 to $570/night

    Irene 506- Ocean City, MD

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $146 to $400/night

    Thunder Island 157D

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $115 to $271/night

    Bay Vista 102

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $194 to $478/night

    Atlantis 909

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $164 to $320/night

    Baywatch III 302A

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $72 to $179/night

    Westward Ho 203

    Studio BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $150 to $290/night

    Club Ocean Villas II 19

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $115 to $340/night

    Thunder Island 75B

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $159 to $434/night

    Thunder Island 7A

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $152 to $524/night

    Bimini 105

    2 BedroomsBathroomsSleeps 8
    4 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $213 to $400/night

    Thunder Island 114C

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $165 to $581/night

    Downtown 2BR Apartment near Convention Center

    2 BedroomsBathroomsSleeps 5
    1 night minstay
    Pets OK
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $291 to $797/night

    Beachwalk II 12

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $140 to $340/night

    Thunder Island 67B

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $211 to $332/night

    The Lodge at Wisp-1 BDRM Luxury Apartment Sleeps 4

    Multiple Units Available
    1 night minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $170 to $401/night

    Barge Road 136O9

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $136 to $343/night

    Salty Sands I 402

    1 Bedroom BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $155 to $638/night

    Crab Cove On The Bay 407

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $175 to $462/night

    Thunder Island 10A

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $363 to $1,502/night

    The Charleston 201

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $183 to $383/night

    High Point South 3E

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $139 to $402/night

    Baltimore's Best Home Away From Home

    2 BedroomsBathroomsSleeps 4
    1 night minstay
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $152 to $454/night

    Sandpiper Dunes 605

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $155 to $286/night

    Harbour Bay 19

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $164 to $478/night

    Crab Cove On The Bay 406

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $104 to $351/night

    Ocean Trail 102

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $204 to $467/night

    Sungate 402

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $115 to $240/night

    Fountainhead 702

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $155 to $391/night

    Sea Jay Townhouse 616C

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $184 to $1,179/night

    Harbour Island 46G

    2 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $194 to $411/night

    Thunder Island 43B

    2 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $104 to $304/night

    Worcester House 302

    1 Bedroom BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $87 to $240/night

    Mirabella 1D

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $170 to $944/night

    Harbour Island 306L

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $175 to $578/night

    Ocean Hideaway 508

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $115 to $421/night

    Thunder Island 141D

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $155 to $400/night

    Thunder Island 61B

    2 BedroomsBathroomsSleeps 9
    3 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $115 to $266/night

    Montego Bay-Peachtree Road 122

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $146 to $411/night

    Fountain Road Home

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $130 to $329/night

    Braemar 503N

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $130 to $279/night

    Blaire Isle 101N

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations