Title: Caroline County Vacation Home Rentals from CA $535: Search Top Private Vacation Homes for Rent | Expedia.ca [Caroline County Hotels](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Hotel-Destinations)[Vacation Rentals in Caroline County](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Vacation-Rental-Destinations)[Caroline County Car Rentals](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Car-Rental-Destinations)[Caroline County Vacations](https://expedia.ca/Caroline-County.d553248635976434148.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/49aeb39d1297aa325883028ae03bfba2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Caroline County Vacation Rentals ## Compare and save ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Caroline County ![](https://mediaim.expedia.com/destination/2/7d84acc9eed28536680439b6391ae18c.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Denton [](https://expedia.ca/Denton-Private-Vacation-Homes.d6048051-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/347de59302f62ebaca58aa45d4fe173d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ridgely [](https://expedia.ca/Ridgely-Private-Vacation-Homes.d151310-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/1/e656c6eefce865189ec0da2e321c8605.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Preston [](https://expedia.ca/Preston-Private-Vacation-Homes.d3000440824-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Featured Vacation Homes in Caroline County ![Interior](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/35cc2c57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/94be7c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/d3ec6332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119430000/119421100/119421004/3d6049ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom Ranch in delightful Dover with AC Dover [](https://www.expedia.ca/Dover-Hotels-Charming-3-Bedroom-Ranch-In-Delightful-Dover-With-AC.h119421004.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) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/9ab957a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/100000000/99690000/99684200/99684191/c7785aa6.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) ### Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina Cambridge 9.6/10 Exceptional (19) "Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron N. CA $238 CA $535 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/df5a2ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/795447d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/569495f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559917/79f373ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cottage on the Miller farm. Milford 10/10 Exceptional (235) "We’ve stayed here several timesWe always feel welcome and the cottage is perfect!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron F. [](https://www.expedia.ca/Milford-Hotels-Cozy-Cottage-On-The-Miller-Farm.h23559917.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/ac0c320c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/9b1c6ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/611460b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/69201425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Quarters Frederica 9.8/10 Exceptional (101) "This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Criselle A. [](https://www.expedia.ca/Dover-Hotels-Captains-Quarters.h67325935.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/47c309cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/c472e480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/4d3b692f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/86338eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Everything House Saint Michaels 10/10 Exceptional (83) "Great location to all shopping and restaurants! Walk to Blue Crab coffee behind back yard! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim D. [](https://www.expedia.ca/St-Michaels-Hotels-Walk-To-Everything-House.h57931801.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/45401e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/e5657076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/53927f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88320000/88312200/88312172/924ba8ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Estate w Private Pier, Game Room & Bar Centreville 9.8/10 Exceptional (32) "Great place! Lots of room to spread our multigenerational family out and get together. Beautiful view of the Corsica River!! Close to everything but extremely private. And everyone enjoyed the game room. Definitely would stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon R. [](https://www.expedia.ca/Centreville-Hotels-Waterfront-Estate-W-Private-Pier.h88312172.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/5058fafc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/43e873ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/1666ec61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/2f4a6949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf Frederica 9.4/10 Exceptional (3) "Adorable cottage. Excellent location. We will definitely rent again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ed M. [](https://www.expedia.ca/Frederica-Hotels-Charming-Bungalow-Water-Views-In-Bowers-Beach-AC-WiFi-Dover-Downs-AFB-DE-Turf.h111870337.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/97000000/96020000/96019000/96018976/aa91462e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96020000/96019000/96018976/e75b5c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96020000/96019000/96018976/be5ae28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/97000000/96020000/96019000/96018976/fdfaf31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf! Frederica 10/10 Exceptional (27) "Loved the house and location. We loved being close to a quiet beach area. The local restaurant was the best food we had on the trip. The host was easy to work with and great at communication. We would stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janova L. [](https://www.expedia.ca/Frederica-Hotels-NEW-Bowers-Retreat-Sleeps-10-Steps-To-Beach-10-Minutes-To-DE-Turf.h96018976.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102860000/102851200/102851162/55a5a1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102860000/102851200/102851162/09cfc25a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/103000000/102860000/102851200/102851162/07f345e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102860000/102851200/102851162/cc7c4167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heated pool, sandy beach, pier, and playground set punch point apart! Sherwood 10/10 Exceptional (11) "Wonderful property with everything you would need to have a great family vacation. Marissa was a great hostess! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. [](https://www.expedia.ca/Sherwood-Hotels-Heated-Pool.h102851162.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100710000/100700400/100700371/w1799h1199x1y1-8b5ca72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100710000/100700400/100700371/w1799h1199x1y1-796b2234.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100710000/100700400/100700371/w1800h1199x0y1-0897c858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/101000000/100710000/100700400/100700371/w1799h1199x1y1-f1d09820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning Tilghman 10/10 Exceptional (10) "We were looking for a relaxing vacation spot for the week and this place exceeded our expectations! The property itself is beautiful and spacious. We loved being in the pool and watching the boats go by. The property manager also had attentive communication with us. Overall, it was a great stay and we would certainly recommend the place to anyone, and hopefully stay again for ourselves. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly R. [](https://www.expedia.ca/Tilghman-Hotels-NEW-LISTING-Waterfront-Bliss-Ultimate-Tilghman-Retreat.h100700371.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102360000/102352700/102352631/79c04d7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102360000/102352700/102352631/7d3b117c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/103000000/102360000/102352700/102352631/c8bcab90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102360000/102352700/102352631/7702ddc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Waterfront Stay close to St. Michaels Easton 9.8/10 Exceptional (14) "Great girls weekend getaway. Wonderful location and spacious accommodations. Enjoyed a relaxing stay and beautiful setting." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Y. [](https://www.expedia.ca/Easton-Hotels-Serene-Waterfront-Minutes-From-St-Michaels.h102352631.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103600000/103597800/103597722/0afbb62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103600000/103597800/103597722/e1fc1eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103600000/103597800/103597722/f17baa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103600000/103597800/103597722/c7e4fd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape with family or friends to this peaceful, 4-bedroom retreat on the water Cambridge 10/10 Exceptional (8) "My family and I stayed here for 5 nights and we couldn’t say enough great things about the property! It was peaceful, clean, and had beautiful views of the lake. My kids enjoyed fishing off the dock. The host was amazing as well. Another plus were the super comfortable beds. Would highly recommend this property if staying in this area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christy M. [](https://www.expedia.ca/Cambridge-Hotels-Escape-With-Family-Or-Friends-To-This-Peaceful.h103597722.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/e6a8684a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/3c396535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/b1332ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/8a9eaa37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! Chestertown 10/10 Exceptional (83) "One of our favorite spots! Never disappoints." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) victoria g. [](https://www.expedia.ca/Chestertown-Hotels-Private-Waterfront-Paradise-W-Pier-Kayak-To-Historic-Chestertown.h64993941.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/3322589a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/849df086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/1ded8f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/101000000/100800000/100794400/100794304/w902h683x61y0-ef852e57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodwind Manor on the Tred Avon minutes to St Michaels and Easton. Easton 10/10 Exceptional (11) "I can't believe we found this gem for our family vacation! The house is gorgeous and full of charm. It was well stocked and impeccably kept. A great week spent fishing, crabbing, kayaking, exploring and swimming. Looking forward to future visits!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pam B. [](https://www.expedia.ca/Easton-Hotels-Woodwind-Manor-On-The-Tred-Avon-Minutes-To-St-Michaels-And-Easton.h100794304.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/92000000/91560000/91559200/91559122/b1d7c3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/92000000/91560000/91559200/91559122/2583cac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/92000000/91560000/91559200/91559122/aa82e925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91560000/91559200/91559122/9a96a593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Delmar Home ~ 7 Mi to Salisbury! Delmar 9.2/10 Wonderful (15) "We absolutely enjoyed staying at this property. Clean and easy to get to the places we wanted to go. Would recommend as a great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Delmar-Hotels-NEW-Tranquil-Delmar-Home-7-Mi-To-Salisbury.h91559122.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116760000/116758400/116758334/d938419c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116760000/116758400/116758334/3b25005c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116760000/116758400/116758334/07894d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/117000000/116760000/116758400/116758334/edad806a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Treehouse with Large Deck Harrington 10/10 Exceptional (12) "We had a wonderful time and the Treehouse was perfect, very clean, thoughtful owner! Wish we had more time to enjoy!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandi S. [](https://www.expedia.ca/Greenwood-Hotels-Luxury-Treehouse-With-Large-Deck.h116758334.Hotel-Information) ![Private beach](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/caba515d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/b49e7cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/c387167f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92610000/92607300/92607228/f992df15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access Sherwood 10/10 Exceptional (18) "House was great and the golf cart excellent" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradley E. [](https://www.expedia.ca/Sherwood-Hotels-Time-Stands-Still.h92607228.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/9bbf68fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, travel crib, free WiFi](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/w800h599x0y1-c77560c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/780a1972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33710000/33706000/33705957/fced1e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW Cambridge 9.8/10 Exceptional (133) "Great location with lots of privacy. The dock and the kayaks were a great hit with the family. Really no need to go anywhere. The house was really nice and very spacious. Some of the amenities like the grill and kitchen supplies could use some updating. A nice place to unwind with family and friends." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa T. [](https://www.expedia.ca/Cambridge-Hotels-Waterfront-Family-Retreat-With-Gorgeous-Views-And-A-Large-Deepwater-Dock-5-MLW.h33705957.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/fbbf0dca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/fb30270a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/f45a57f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/115000000/114390000/114380200/114380126/e0fcab5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RELAX- Eastern Shore Creek Home - 6 Guests Grasonville 10/10 Exceptional (5) "We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherry N. [](https://www.expedia.ca/RELAX-Eastern-Shore-Creek-Home.h114380126.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/31813fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/e6532040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/8a18018c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/62000000/61590000/61585600/61585503/b09248c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dollhouse in Central Historic St Michaels St Michaels 9.6/10 Exceptional (55) "Great location. House is old and therefore a little quirky, but overall comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen L. [](https://www.expedia.ca/St-Michaels-Hotels-Dollhouse-In-Central-Historic-St-Michaels.h61585503.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=2025-11-14&endDate=2025-11-15®ionId=553248635976434148&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%2FCaroline-County-Private-Vacation-Homes.d553248635976434148-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCaroline-County-Private-Vacation-Homes.d553248635976434148-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Caroline County Hotel Reviews ![Hampton Inn Salisbury](//images.trvl-media.com/lodging/1000000/290000/282000/281943/633fd984_y.jpg) ### Hampton Inn Salisbury 10/10 Excellent "Overall great, 3rd time staying at this hotel." [](https://expedia.ca/Salisbury-Hotels-Hampton-Inn-Salisbury.h281943.Hotel-Information) ![Tru by Hilton Georgetown](//images.trvl-media.com/lodging/37000000/36250000/36247600/36247517/43c13260_y.jpg) ### Tru by Hilton Georgetown 10/10 Excellent "Yes" [](https://expedia.ca/Rehoboth-Beach-Hotels-Tru-By-Hilton-Georgetown.h36247517.Hotel-Information) ![Hilton Garden Inn Dover](//images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/eab21539_y.jpg) ### Hilton Garden Inn Dover 10/10 Excellent "Always love staying there its always nice" [](https://expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information) ![Microtel Inn & Suites by Wyndham Milford](//images.trvl-media.com/lodging/65000000/64920000/64916800/64916777/3f703075_y.jpg) ### Microtel Inn & Suites by Wyndham Milford 10/10 Excellent "Great" [](https://expedia.ca/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Milford.h64916777.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 "Pleasant staff, clean accommodations although could benefit from a modern upgrade. Restaurant was knowledgeable and helpful in assisting my wife with accommodating celiac options. " [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Springhill Suites By Marriott Frederica](//images.trvl-media.com/lodging/96000000/95070000/95062700/95062671/9f69013a_y.jpg) ### Springhill Suites By Marriott Frederica 10/10 Excellent "Excellent " [](https://expedia.ca/Frederica-Hotels-Springhill-Suites-By-Marriott-Frederica.h95062671.Hotel-Information) ![Bally's Dover Casino Resort](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "Everything was great always nice when i stay here" [](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Holiday Inn Express Hotel & Suites Dover by IHG](//images.trvl-media.com/lodging/1000000/600000/597800/597727/6d0ff772_y.jpg) ### Holiday Inn Express Hotel & Suites Dover by IHG 10/10 Excellent "Great hotel staff from front desk, custodial, housekeeping, breakfast staff..especially older African American Lady who handles breakfast Thursday and Friday mornings of our stay. Will definitely return." [](https://expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information) ![Red Roof Inn & Suites Dover Downtown](//images.trvl-media.com/lodging/1000000/890000/888000/887960/473c4e31_y.jpg) ### Red Roof Inn & Suites Dover Downtown 10/10 Excellent "Safe area. Clean room, friendly staff, plenty of parking. " [](https://expedia.ca/Dover-Hotels-Red-Roof-Inn-Suites-Dover-Downtown.h887960.Hotel-Information) ## Find out more about Caroline County ## Caroline County Vacation Homes information | Number of reviews | 848 | | --- | --- | | Accommodation | 316 Vacation Homes | | Lowest Price | CA $535 | | Highest Price | CA $535 | ## 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) - [Centreville Hotels](https://www.expedia.ca/Centreville-Hotels.d88125.Travel-Guide-Hotels) - [B&B in Cordova](https://www.expedia.ca/Cordova-Bed-And-Breakfast.d3000440540-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Luxury Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Luxury-Hotel.0-0-d6025644-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Oceanfront-Hotels.0-0-d6025644-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Pet-Friendly-Hotel.0-0-d6025644-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Romantic-Hotel.0-0-d6025644-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Shopping-Hotel.0-0-d6025644-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Spa-Hotel.0-0-d6025644-tSpaHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Hotels-Winery-Hotel.0-0-d6025644-tWineryHotel.Travel-Guide-Filter-Hotels) - [Eastern Shore Hotels](https://www.expedia.ca/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels) - [Inns in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Inns.d6025644-aaInns.Travel-Guide-Accommodation) - [Motels in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Motels.d6025644-aaMotels.Travel-Guide-Accommodation) - [Resorts in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Resort-Hotels.d6025644-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Eastern Shore](https://www.expedia.ca/Eastern-Shore-Townhomes.d6025644-aaTownhomes.Travel-Guide-Accommodation) - [Farmstay in Easton](https://www.expedia.ca/Easton-Agritourism.d7120-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Easton](https://www.expedia.ca/Easton-Bed-And-Breakfast.d7120-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Easton](https://www.expedia.ca/Easton-Hotels-Beach-Hotel.0-0-d7120-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Easton](https://www.expedia.ca/Easton-Hotels-Boutique-Hotel.0-0-d7120-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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[Wye Mills Hotels](https://www.expedia.ca/Wye-Mills-Hotels.d6359185.Travel-Guide-Hotels) - [Flights to Eastern Shore](https://www.expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights) - [Flights from Preston](https://www.expedia.ca/lp/flights/3000440824/flights-from-preston) - [Flights from Queen Anne](https://www.expedia.ca/lp/flights/553248634998599471/flights-from-queen-anne) - [Flights from Wye Mills](https://www.expedia.ca/lp/flights/6359185/flights-from-wye-mills) - [Flights from Allentown (ABE) to Easton (ESN)](https://www.expedia.ca/lp/flights/abe/esn/allentown-to-easton) - [Flights from Cincinnati (CVG) to Easton (ESN)](https://www.expedia.ca/lp/flights/cvg/esn/cincinnati-to-easton) - [Flights from Washington (DCA) to Easton (ESN)](https://www.expedia.ca/lp/flights/dca/esn/washington-to-easton) - [Flights from Dallas (DFW) to Easton (ESN)](https://www.expedia.ca/lp/flights/dfw/esn/dallas-to-easton) - [Flights from New York (JFK) to Easton (ESN)](https://www.expedia.ca/lp/flights/jfk/esn/new-york-to-easton) - [Flights from Los Angeles (LAX) to Easton (ESN)](https://www.expedia.ca/lp/flights/lax/esn/los-angeles-to-easton) - [Flights from West Palm Beach (PBI) to Easton (ESN)](https://www.expedia.ca/lp/flights/pbi/esn/west-palm-beach-to-easton) - [Eastern Shore Vacations](https://www.expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides) - [Visit Eastern Shore](https://www.expedia.ca/Eastern-Shore.dx6025644) - [Visit Easton](https://www.expedia.ca/Easton.dx7120) - [Wye Landing](https://www.expedia.ca/Wye-Landing-Wye-Mills.d553248621532662354.Vacation-Attraction) - [Avis Rental Cars in Easton](https://www.expedia.ca/Avis-Car-Rentals-In-Easton.d7120-c41.Car-Rental-Guide-Suppliers) - [Car rental Denton](https://www.expedia.ca/Car-Rentals-In-Denton.d6048051.Car-Rental-Guide) - [Car rentals near Eastern Shore](https://www.expedia.ca/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide) - [Rental cars Easton - Newnam airport](https://www.expedia.ca/Car-Rentals-In-Easton-Newnam.d6027707.Car-Rental-Guide) - 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