Title: Caroline County Vacation Home Rentals from CA $388: 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 ![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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976434148&startDate=2025-12-19&endDate=2025-12-21&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 ![Property grounds](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/5d4c0868.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/664d3b8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/ecdbd6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/111000000/110630000/110624500/110624456/8a3e2d7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf Greenwood 9.8/10 Exceptional (24) "Great place to stay with a family. Very nicely decorated and clean. " [](https://www.expedia.ca/Greenwood-Hotels-Backroad-Getaway-Newly-Build-3-Bedroom-Retreat-In-Greenwood-With-WiFi.h110624456.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/d6394886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/cdb20515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/c299076c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89180000/89179200/89179147/c261da12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock Cambridge 9.8/10 Exceptional (7) "Great House " [](https://www.expedia.ca/Cambridge-Hotels-NEW-Gorgeous-Waterfront-Estate-In-Cambridge-Md.h89179147.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) ![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 $223 CA $495 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Cambridge-Hotels-Cozy-2-Bedroom.h99684191.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/75c5aef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/6355b849.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/2e4f627e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/77000000/76260000/76259800/76259762/c73dd104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### RANCH AT ROYAL OAK- Exclusive waterfront pool pier Royal Oak 10/10 Exceptional (26) "Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon." [](https://www.expedia.ca/Royal-Oak-Hotels-RANCH-AT-ROYAL-OAK-Exclusive-Waterfront-Pool-Pier.h76259762.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/68000000/67330000/67326000/67325935/dc11b11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Quarters Frederica 9.8/10 Exceptional (99) "This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. " [](https://www.expedia.ca/Dover-Hotels-Captains-Quarters.h67325935.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1424h945x1y0-5f4c2bf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/f78fd6e7_edited_e2a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1440h960x0y2-2947a2af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, table tennis, books](https://images.trvl-media.com/lodging/109000000/108390000/108385700/108385645/w1439h951x0y5-b1ec64ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management! East New Market 10/10 Exceptional (2) "Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend" [](https://www.expedia.ca/East-New-Market-Hotels-Belle-Aire-Landing-Spacious-Large-Estate-Under-New-Management.h108385645.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/cc07a31f.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) ![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 (54) "This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay." [](https://www.expedia.ca/St-Michaels-Hotels-Dollhouse-In-Central-Historic-St-Michaels.h61585503.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/88000000/87900000/87899700/87899660/1ed9bf0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87900000/87899700/87899660/eefb4e61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87900000/87899700/87899660/89480e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87900000/87899700/87899660/cd2d4388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Delmar Delmar 10/10 Exceptional (6) "We were able to do some cooking, relax in the evening and play some rounds of pool. Everything was great." [](https://www.expedia.ca/Delmar-Hotels-Vacation-Home-In-Delmar.h87899660.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/e3526265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/f3c5c074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/4e7c5213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/c370010d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Circa 1900 Home in the Heart of Historic Downtown Chestertown Chestertown 10/10 Exceptional (74) "Great house, will stay again in the future. " [](https://www.expedia.ca/Chestertown-Hotels-Circa-1900-Home-In-The-Heart-Of-Historic-Downtown-Chestertown.h66473084.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) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/49fd9b22.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) ![Game room](https://images.trvl-media.com/lodging/97000000/96120000/96117900/96117871/c3524691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Waterfront Retreat in Cambridge! Cambridge 10/10 Exceptional (47) "Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. " CA $314 CA $623 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Cambridge-Hotels-Beautiful-Waterfront-Retreat-In-Cambridge.h96117871.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72040000/72034400/72034352/6ca90037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72040000/72034400/72034352/62e9bfa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/73000000/72040000/72034400/72034352/5a5aebf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/73000000/72040000/72034400/72034352/15b9a34b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lee's Place Brand New 2BR Townhouse w/free parking Milford 9.4/10 Exceptional (28) "It was a great option for our Lacrosse weekend!" [](https://www.expedia.ca/Milford-Hotels-Lees-Place-Brand-New-2BR-Townhouse-Wfree-Parking.h72034352.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) ![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) ![Interior](https://images.trvl-media.com/lodging/112000000/111880000/111870400/111870337/96d11b7a.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) ### 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. " [](https://www.expedia.ca/Frederica-Hotels-Charming-Bungalow-Water-Views-In-Bowers-Beach-AC-WiFi-Dover-Downs-AFB-DE-Turf.h111870337.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/b94b1ba5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c62e911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/38fa4ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c8f8b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife St. Michaels 9.8/10 Exceptional (43) "Wonderful home in excellent location!!" [](https://www.expedia.ca/St-Michaels-Hotels-Carpenter-Alley-Newly-Renovated-Cottage-In-Center-Of-Historic-St-Michaels.h48378570.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/4ec52bf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/bc027eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/42f3eb31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/86000000/85390000/85383900/85383832/ad4965a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thorneton Point Estate Easton 9.6/10 Exceptional (20) "Beautiful, well-maintained property in a gorgeous waterside setting. " [](https://www.expedia.ca/Easton-Hotels-Thorneton-Point-Estate.h85383832.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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/4d3b692f.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) ![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) "Clean and nice place to stay" [](https://www.expedia.ca/St-Michaels-Hotels-Walk-To-Everything-House.h57931801.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113090000/113085600/113085507/ea4f68e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113090000/113085600/113085507/c2d7a90a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/114000000/113090000/113085600/113085507/cb48ad5b.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/114000000/113090000/113085600/113085507/4132193f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delaware Turf Bungalow’s Sister! Milford 10/10 Exceptional (1) "This bungalow was the perfect getaway for the weekend. It was clean, cozy and had enough space for my children and I to relax without being on top of each other. We were close enough to several beaches and the boardwalk but far enough away to get away from the hustle and bustle of the big beach town. The host was amazing. She was so nice to communicate with and very accommodating. She made us feel very welcomed and even suggested some sights to check out around the area. The whole experience was... [](https://www.expedia.ca/Milford-Hotels-Delaware-Turf-Bungalows-Sister.h113085507.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/ae7d8ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/5457dac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/24ab4beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99290000/99280700/99280632/265dbeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lark's Nest on the Chester River. Spacious, waterfront home with private dock. Millington 9.6/10 Exceptional (22) "Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! " [](https://www.expedia.ca/Millington-Hotels-Larks-Nest-On-The-Chester-River-Spacious.h99280632.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) ![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) ![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) ![Dining](https://images.trvl-media.com/lodging/81000000/80030000/80024200/80024112/w508h683x258y0-7ad5c2e6.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 $320 CA $388 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Woolford-Hotels-Waterfront-Getaway-With-Dock.h80024112.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/103000000/102420000/102416100/102416036/b88cfd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102420000/102416100/102416036/420d61f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102420000/102416100/102416036/640b83e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/103000000/102420000/102416100/102416036/0713f79c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Front, Private Single Family Home Grasonville 10/10 Exceptional (19) "Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! " [](https://www.expedia.ca/Grasonville-Hotels-River-Front.h102416036.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/e20872d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/eb53d0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/2eb71d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92930000/92922000/92921948/b76f489a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-Bedroom Retreat: Modern, Pet-Friendly Tilghman Island 10/10 Exceptional (13) "The space was perfect for our group. We enjoyed the food at Two If By Sea and at the country store - both were in walking distance. " [](https://www.expedia.ca/Tilghman-Hotels-4-Bedroom-Retreat-Modern.h92921948.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=2025-10-12&endDate=2025-10-13®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 ![Hyatt Place Kent Narrows & Marina](//images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Great location and rooms. Great place!" [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Hampton Inn Milford](//images.trvl-media.com/lodging/4000000/3650000/3645000/3644980/3ed7ec07_y.jpg) ### Hampton Inn Milford 10/10 Excellent "Signs need to be added at the entrances to indicate driveways. In addition lighting at entrances. We went out & came back at dusk & even though we had GPS it wasn’t easy to find entrances. Can’t imagine what it would be in the dark." [](https://expedia.ca/Dover-Hotels-Hampton-Inn-Milford.h3644980.Hotel-Information) ![Microtel Inn & Suites by Wyndham Dover](//images.trvl-media.com/lodging/2000000/1510000/1509700/1509695/b1bab4b1_y.jpg) ### Microtel Inn & Suites by Wyndham Dover 10/10 Excellent "Great " [](https://expedia.ca/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Dover.h1509695.Hotel-Information) ![Comfort Inn & Suites](//images.trvl-media.com/lodging/2000000/1840000/1831100/1831095/c1d84f60_y.jpg) ### Comfort Inn & Suites 10/10 Excellent "This is our 4th, 5th or 6th stay here (lost count) and always find the staff very friendly and courteous. The rooms are always clean, beds are so comfortable (Thank You!), air conditioner works, and the breakfast is wonderful! It's like a full on breakfast and the lady that's in charge of it keeps everything stocked and counters wiped down. Excellent experience that every hotel should use as a model. " [](https://expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1831095.Hotel-Information) ![Comfort Inn & Suites Milford](//images.trvl-media.com/lodging/2000000/1180000/1178300/1178282/2bacc227_y.jpg) ### Comfort Inn & Suites Milford 10/10 Excellent "Customer service was great. Clean rooms with comfortable beds and perfect water temperature for shower. Everything one would need in the room ie microwave, refrigerator and toiletry. Happy with our choice." [](https://expedia.ca/Dover-Hotels-Comfort-Inn-Suites.h1178282.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 "The facility was very clean & comfortable. The only thing that would have been better, if the hotel check in area was better marked (as their check in area), and if the desk for that was closer to the entrance door. It was a walk across a very large area, inside the building, which was hard if you use a walker or cane." [](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.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 "It had a unique layout for clothing; a computer desk, couch, reading lounge spot. " [](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 "Beautiful place" [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Easy Check In & quite area" [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ## Find out more about Caroline County ## Caroline County Vacation Homes information | Number of reviews | 627 | | --- | --- | | Accommodation | 343 Vacation Homes | | Lowest Price | CA $388 | | Highest Price | CA $623 | ## 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) - 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