Save $97Preferred hostEntire home in Queenstown, MDDec 16 - 19$339/nightNew Star Icon 98a39ebb2ba8cfaab53eed08da342ae75.014 bedrooms8 guests$1,211$1,114total
Save $433Preferred hostEntire home in Queenstown, MDNov 16 - 19$1,514/nightNew Star Icon d94e8b281c539f1807fc811f6f06ed535.035 bedrooms10 guests$5,411$4,978total
Save $165Preferred hostEntire home in Grasonville, MDApr 29 - May 2$575/nightNew Star Icon 5f93d66be1f42af526581bc4ffb2c4bf5.053 bedrooms8 guestsPay only $219 today$2,056$1,892total
Save $138House in Grasonville, MDNov 29 - Dec 2$484/nightNew Star Icon a4f2ee0dc559a5c88ff0de9b866ba900New4 bedrooms8 guests$1,729$1,591total
Save $172House in Chester, MDNov 16 - 19$330/nightNew Star Icon 90ecca0db88f140c9a183babd40ca03bNew4 bedrooms10 guests$1,262$1,089total
Save $324Preferred hostEntire home in Stevensville, MDNov 16 - 19$970/nightNew Star Icon 6147fc16227f232c4ac42e43683271144.973 bedrooms11 guests$3,515$3,191total
Save $78Preferred hostEntire home in Rock Hall, MDNov 16 - 19$274/nightNew Star Icon 9506f070f9011ecd0f37c5dfed46adad5.023 bedrooms6 guests$979$900total
Save $205Preferred hostHouse in Stevensville, MDNov 16 - 19$467/nightNew Star Icon 84ff27b744a49b01b2724a07da72e7694.9123 bedrooms6 guests$1,681$1,476total
Save $71Preferred hostEntire home in Chestertown, MDNov 16 - 19$211/nightNew Star Icon efe5478aeab10160cf121cabbbdc26cb4.333 bedrooms6 guests$765$693total
Save $84Preferred hostEntire cottage in Annapolis, MDNov 16 - 19$287/nightNew Star Icon 6c4cab84092bdaab78b4545804d92ea64.043 bedrooms5 guests$1,051$967total
Save $151House in St. Michaels, MDNov 16 - 19$394/nightNew Star Icon 4ea4bbae0aa68494ace3f873391426985.011 bedroom4 guests$1,440$1,288total
Save $135House in Annapolis, MDDec 20 - 23$458/nightNew Star Icon 205b57216ee06517c3d22d9bc096da165.0103 bedrooms8 guests$1,686$1,551total
Save $130Preferred hostEntire home in Annapolis, MDNov 16 - 19$443/nightNew Star Icon 9ba9d2669211929554a0096db12c13d65.014 bedrooms8 guests$1,622$1,492total
Save $305Preferred hostEntire home in Bozman, MDNov 16 - 19$526/nightNew Star Icon 9b8ce1377931c63b2fdb83ced97e74fa5.014 bedrooms8 guests$2,019$1,715total
Save $128Preferred hostEntire home in Chestertown, MDNov 16 - 19$222/nightNew Star Icon bb0fa09d6d2d8906c089ea456ade20225.0172 bedrooms6 guests$859$731total
Save $220Preferred hostEntire home in Chestertown, MDNov 16 - 19$770/nightNew Star Icon c5972cfc3528585335f0cf9a81652e735.034 bedrooms14 guests$2,752$2,532total
Save $281Whimstay gemHouse in Chestertown, MDNov 16 - 19$375/nightNew Star Icon 75fafd8a97f8dff71e40dfb3a39c18fe5.01073 bedrooms10 guests$1,519$1,238total
Save $182Preferred hostHouse in Annapolis, MDDec 8 - 11$619/nightNew Star Icon 5a5f664d63429fd61616f7492c5bc5db5.0193 bedrooms8 guests$2,278$2,096total
Save $261Preferred hostCottage in Annapolis, MDNov 16 - 19$511/nightNew Star Icon 6de746f50914c2f9eff699f09612cd9f4.8183 bedrooms8 guests$1,991$1,730total
Save $228Whimstay gemHouse in Annapolis, MDNov 16 - 19$276/nightNew Star Icon f6dc88a351ef8cd986bbfc0a4271ede94.9272 bedrooms4 guests$1,162$934total
Save $426Preferred hostHouse in Annapolis, MDDec 31 - Jan 3$726/nightNew Star Icon 30612b42a68fbd0d21617f930d1551fb4.6192 bedrooms7 guests$2,882$2,456total