Title: St. Michaels Vacation Home Rentals from CA $345: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in St. Michaels](https://expedia.ca/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)[Vacation Rentals in St. Michaels](https://expedia.ca/St-Michaels-Vacation-Rentals.d5940.Travel-Guide-VacationRentals)[Flights to St. Michaels](https://expedia.ca/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)[St. Michaels Car Rentals](https://expedia.ca/Car-Rentals-In-St-Michaels.d5940.Car-Rental-Guide)[St. Michaels Vacation Packages](https://expedia.ca/St-Michaels.d5940.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/e708a2ddef7b36b18845a12b959447e3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # St. Michaels Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select St. Michaels Vacation Homes ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/c77382da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/80cf0fdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/b482bb5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063700/84063656/12356e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax on Kent Island in 3 Bedroom Home w/Waterview Stevensville 9.8/10 Exceptional (40) "We had a great stay! The property has everything we needed and host was easy to communicate with " CA $95 CA $346 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Stevensville-Hotels-Relax-On-Kent-Island-In-3-Bedroom-Home-WWaterview.h84063656.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/51cd6ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/b3c1fc85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/9ab957a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/1792ceb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina Cambridge 9.6/10 Exceptional (15) "Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. " CA $244 CA $543 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/3c8498e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/259066d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/9eb7ac3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HGTV quality, private guest suite, country getaway with hot tub & fire pit Centreville 10/10 Exceptional (6) "This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! " CA $275 CA $611 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/c53ddff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/da0262a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/4ee38359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/85000000/84070000/84063900/84063895/89a58d5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️ Stevensville 9.6/10 Exceptional (30) "Nice and peaceful stay for a quick local getaway. " CA $95 CA $345 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Stevensville-Hotels-Charming-CoastalCountry-Home-W3-Acres-Sauna.h84063895.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/de679fa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/efcaae35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/b08b990c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/88000000/87800000/87799500/87799498/6e19a811.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable two-bedroom retreat close to Easton, Denton, Centreville Queen Anne 10/10 Exceptional (26) "Quiet, quaint....perfect" CA $243 CA $475 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Adorable-Two-Bedroom-Retreat-Close-To-Easton.h87799498.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/44a64359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. Grasonville 9.6/10 Exceptional (12) "Nice stay, would book again. Needs new king mattress, more mirrors in the home and a water filter. Very relaxing clean, makess you want to stay in and gamg out. Close to everything cool." CA $349 CA $584 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/8ae0a25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/166bb313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/a2c7c68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83930000/83922000/83921931/882747f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Cottage steps from Rock Hall Harbor Rock Hall 10/10 Exceptional (2) "Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!" CA $244 CA $498 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Rock-Hall-Hotels-Bayside-Cottage-Steps-From-Rock-Hall-Harbor.h83921931.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/e7ff4058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/c3524691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/5ae97cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/4d65add6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Waterfront Retreat in Cambridge! Cambridge 10/10 Exceptional (47) "Property was as listed. We enjoyed are stay." CA $314 CA $624 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Cambridge-Hotels-Beautiful-Waterfront-Retreat-In-Cambridge.h96117871.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w507h683x258y0-d94bdb39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w508h683x258y0-88a539de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w507h683x259y0-684aae50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w506h683x259y0-568e095d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Getaway with Dock Woolford 10/10 Exceptional (51) "Great location with everything you may need. It is close to restaurants and Emily’s produce.2nd time staying and will be back again. " CA $321 CA $376 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Woolford-Hotels-Waterfront-Getaway-With-Dock.h80024112.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/aaa820d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/67700a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d4e67bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants North Beach 10/10 Exceptional (30) "Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. " CA $212 CA $650 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/a01170f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/f1bbce3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/62242b9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103760000/103759100/103759056/e90ef5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE Cambridge 8.8/10 Excellent (9) "This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay." CA $482 CA $887 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Cambridge-Hotels-WATERFRONT-HOT-TUB-4-BED4-BATH-CHARMING-HOME-IN-THE-HEART-OF-CAMBRIDGE.h103759056.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/7fd63e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/2b76d904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/053c923e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/64000000/63650000/63641700/63641659/bb60f922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Breezes - quiet waterfront retreat Dorchester County 10/10 Exceptional (40) "Good time with my friends " [](https://www.expedia.ca/Cambridge-Hotels-Sunset-Breezes-Quiet-Waterfront-Retreat.h63641659.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/3f3bd4d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/9130ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/0e96ebfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69550000/69541400/69541327/bf60932b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Beach! King Bed & Free Beach Passes North Beach 10/10 Exceptional (16) "We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!" CA $137 CA $483 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/North-Beach-Hotels-Plant-Filled-Oasis-Near-Beach-Town-With-Passes-Tips.h69541327.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/w952h953x0y0-b52c439e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/aab800be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/ae401628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96350000/96341600/96341595/c5240202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Beach House: Spacious Deck, Grill & Views Chesapeake Beach 9.0/10 Wonderful (6) "Everything was great. The owner was extremely helpful. Couldn't ask for anything better." CA $205 CA $573 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Beach-Front-Chesapeake-Views-Family-Getaway.h96341595.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/5eca3b46_edited_e784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/10e31f36_edited_f301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/8aaef683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side Shady Side 10/10 Exceptional (2) "The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side." CA $201 CA $589 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/cc3df3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/733d81ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/f9a89b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113280000/113272300/113272210/85376bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Pet-Friendly Stay - Near Bay & Beaches. Annapolis 10/10 Exceptional (3) "Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!" CA $326 CA $788 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-Retreat-Near-The-Bay.h113272210.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b24c0f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/f3fa7d0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/756b8e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/cb12abf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wright's Cottage- Pet's Welcome & EV Charging Annapolis 9.0/10 Wonderful (14) "The property was well cleaned and communication with owner was excellent. Would stay again" CA $287 CA $574 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Annapolis-Hotels-Wrights-Cottage-Pets-Welcome-EV-Charging.h105549011.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/3f6b4c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/d811e5a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/fcc4baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83070000/83066200/83066154/0b964f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WATERFRONT!! \*\*HOT TUB\*\* 3 bedroom Oasis on 2+ acres - Sleeps 8 Cambridge 10/10 Exceptional (13) "very serene, peaceful home on the bay! Amazing getaway! " CA $414 CA $781 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Cambridge-Hotels-WATERFRONT-3-Bed-Oasis-On-2-Acres-Sleeps-8.h83066154.Hotel-Information) ![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/5550ff75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/6067372d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/444cf8e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/106000000/105400000/105392900/105392845/1e7a25cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holly Hill Haven - Sleeps 10 Edgewater 10/10 Exceptional (3) "House was clean and comfortable. Great layout. " CA $207 CA $686 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Edgewater-Hotels-Escape-To-Our-Beautifully-Renovated-Home-In-The-Heart-Of-The-Scenic-Mayo-Peninsula.h105392845.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/60e252be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/7e1ea789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/a4a9eedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96310000/96305200/96305189/d7bd9b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Getaway, Dock Your Boat & Play! Edgewater 10/10 Exceptional (2) "Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. " CA $163 CA $456 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Edgewater-Hotels-Waterfront-Getaway.h96305189.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19®ionId=5940&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSt-Michaels-Private-Vacation-Homes.d5940-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSt-Michaels-Private-Vacation-Homes.d5940-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top St. Michaels Hotel Reviews ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "The hotel was nice. The first room I got was still a mess because housekeeping didn’t clean that room. So I was given another room, which was clean as a whistle. Very good stay. I would definitely go back. Service was top tier." [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Yes" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hyatt Regency Chesapeake Bay](//images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg) ### Hyatt Regency Chesapeake Bay 10/10 Excellent "Indoor and outdoor pools were very clean and nice " [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Great place." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Clean room. Professional staff" [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](//images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Great staff, very helpful and welcoming!! Also location is great and very walkable to downtown area" [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![The Wildset](//images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg) ### The Wildset 10/10 Excellent "Absolutely perfect in all regards. A property to visit again and again!" [](https://expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ![Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch](//images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/954f8aa1_y.jpg) ### Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch 10/10 Excellent "The house is a charming historic home in the perfect location. The house was clean and well-appointed. Thomas replied promptly to our questions and was very accommodating. We would come back. " [](https://expedia.ca/St-Michaels-Hotels-Carpenter-St-Cottage-In-The-Heart-Of-St-Michaels-Village-Large-Screened-Porch.h34582947.Hotel-Information) ## Find out more about St. Michaels ## St. Michaels Vacation Homes information | Number of reviews | 355 | | --- | --- | | Accommodation | 716 Vacation Homes | | Lowest Price | CA $345 | | Highest Price | CA $887 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Eastern Shore](https://www.expedia.ca/4Star-Eastern-Shore-Hotels.s40-0-d6025644.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Eastern Shore](https://www.expedia.ca/5Star-Eastern-Shore-Hotels.s50-0-d6025644.Travel-Guide-Filter-Hotels) - [Hotels near Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) - [Apartments in Bellevue](https://www.expedia.ca/Bellevue-Apartments.d553248635975867527-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Bellevue](https://www.expedia.ca/Bellevue-Condos.d553248635975867527-aaCondos.Travel-Guide-Accommodation) - 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