Title: Caroline County Vacation Rentals : Short-Term Rentals for 2026 | Expedia.ca [Caroline County Hotels](https://expedia.ca/Destinations-In-Caroline-County.d553248635976434148.Hotel-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) ![Aerial view of the Choptank River in Maryland, with calm waters and vibrant greenery](https://images.trvl-media.com/place/553248635976434148/1612c71d-0db1-48cc-9500-863759de3a04.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635976434148/1612c71d-0db1-48cc-9500-863759de3a04.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 ## Our top choices for Caroline County vacation rentals ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112700000/112698500/112698415/1796e228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112700000/112698500/112698415/de24e113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112700000/112698500/112698415/00561e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/113000000/112700000/112698500/112698415/e54fb222.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Mi to Dover Motor Speedway: Pet-friendly Retreat [](https://www.expedia.ca/Dover-Hotels-3-Mi-To-Dover-Motor-Speedway-Pet-Friendly-Retreat.h112698415.Hotel-Information) Dover CA $130 CA $595 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Dover-Hotels-3-Mi-To-Dover-Motor-Speedway-Pet-Friendly-Retreat.h112698415.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=2026-04-20&endDate=2026-04-21®ionId=553248635976434148&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CONDO) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Caroline+County%2C+Maryland%2C+United+States+of+America®ionId=553248635976434148&latLong=38.884558%2C-75.827156&adults=2&startDate=2026-07-04&d1=2026-07-04&endDate=2026-07-07&d2=2026-07-07&lodging=CABIN) ![](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%2FDestinations-In-Caroline-County.d553248635976434148.Vacation-Rental-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Caroline-County.d553248635976434148.Vacation-Rental-Destinations) ## Top Caroline County Hotel Reviews ![Bally's Dover Casino Resort](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/f76eefb5_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "Nice clean room " [](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Microtel Inn & Suites by Wyndham Dover](https://images.trvl-media.com/lodging/2000000/1510000/1509700/1509695/b1bab4b1_y.jpg) ### Microtel Inn & Suites by Wyndham Dover 10/10 Excellent "The room was nice and clean staff was great the room was big plenty of space my next visit I be staying here again" [](https://expedia.ca/Dover-Hotels-Microtel-Inn-Suites-By-Wyndham-Dover.h1509695.Hotel-Information) ![MHO Hotel Dover](https://images.trvl-media.com/lodging/123000000/122150000/122147300/122147246/8957532c_y.jpg) ### MHO Hotel Dover 2/10 Terrible "THIS WAS THE WORST STAY IVE EXPERIENCED. THE ROOM WAS DISGUSTING AND DIRTY" [](https://expedia.ca/Dover-Hotels-MHO-Hotel-Dover.h122147246.Hotel-Information) ![Wyndham Garden Dover](https://images.trvl-media.com/lodging/1000000/530000/520100/520035/cf1236f9_y.jpg) ### Wyndham Garden Dover 4/10 Poor "This hotel was good for just passing through. If I had to stay more then 10 hours I would have left. The rooms were clean on the surface. I have stayed in much worse but this was OK for what I needed it for and that was sleep and then back on the road. The property needs a huge update. The staff was absolutely amazing and friendly and kind. " [](https://expedia.ca/Dover-Hotels-Wyndham-Garden-Dover.h520035.Hotel-Information) ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd_y.jpg) ### Inn at Perry Cabin 8/10 Good "Disappointing. The hotel is lovely but the staff are in training mode and don’t get things quite right. They didn’t tell us there was an Easter brunch so we missed breakfast on Sunday as they had booked out the dining room and everything in town was already full. The food was nice but relatively expensive. When it rains there is nowhere to sit that is not the room or the pub. The pool despite being advertised was not yet open for the season which was of the main reasons we chose the hotel. " [](https://expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "The lady that checked us in was so sweet and helpful." [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Holiday Inn Express Annapolis East-Kent Island by IHG](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566_y.jpg) ### Holiday Inn Express Annapolis East-Kent Island by IHG 6/10 Okay "The room was fine, but the service was not. The staff came across as unfriendly, and the manager was outright passive-aggressive. I booked this hotel specifically because it’s advertised as pet-friendly, yet there was no mention of a $60 pet fee when I made the reservation. When I questioned it, the manager’s response was that other hotels charge $100—which completely misses the point. Be upfront about your fees. To make matters worse, there was a leak in my room. When I reported it, I was told it was coming from the third floor and that I could move rooms. By that point, it was highly inconvenient, and no real effort was made to resolve the situation or accommodate me. Overall, not a great experience. Transparency and basic customer service were lacking." [](https://expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/w5755h3835x5y5-a7434888_y.jpg) ### Hilton Garden Inn Kent Island Marina 10/10 Excellent "Friendly staff " [](https://expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Quality Inn & Suites Harrington - Milford](https://images.trvl-media.com/lodging/1000000/700000/694400/694352/1d5d612d_y.jpg) ### Quality Inn & Suites Harrington - Milford 8/10 Good "Room was fine - there was a very strong odor in the hotel it was very strong " [](https://expedia.ca/Dover-Hotels-Quality-Inn-And-Suites.h694352.Hotel-Information) ## Find out more about Caroline County **Everything you need to know about** **Caroline County** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Caroline County vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Caroline County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Caroline County vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Caroline County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Caroline County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Caroline County vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Caroline County rentals** At Expedia, we put the best Caroline County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Caroline County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Caroline County vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Caroline County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - All accommodation types in Caroline County - [Vacation Homes in Caroline County ](https://expedia.ca/Caroline-County-Private-Vacation-Homes.d553248635976434148-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Caroline County ](https://expedia.ca/Caroline-County-Cottages.d553248635976434148-aaCottages.Travel-Guide-Accommodation) - [Apartments in Caroline County ](https://expedia.ca/Caroline-County-Apartments.d553248635976434148-aaApartments.Travel-Guide-Accommodation) - [B&B in Caroline County ](https://expedia.ca/Caroline-County-Bed-And-Breakfast.d553248635976434148-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Caroline County ](https://expedia.ca/Caroline-County-Motels.d553248635976434148-aaMotels.Travel-Guide-Accommodation) - [Farmstay in Caroline County ](https://expedia.ca/Caroline-County-Agritourism.d553248635976434148-aaAgritourism.Travel-Guide-Accommodation) - [Condo Rentals in Caroline County ](https://expedia.ca/Caroline-County-Condos.d553248635976434148-aaCondos.Travel-Guide-Accommodation) - [Inns in Caroline County ](https://expedia.ca/Caroline-County-Inns.d553248635976434148-aaInns.Travel-Guide-Accommodation) - [Cabin Rentals in Caroline County ](https://expedia.ca/Caroline-County-Cabins.d553248635976434148-aaCabins.Travel-Guide-Accommodation) - [Villas in Caroline County ](https://expedia.ca/Caroline-County-Villas.d553248635976434148-aaVillas.Travel-Guide-Accommodation) - [Houseboats in Caroline County ](https://expedia.ca/Caroline-County-Houseboats.d553248635976434148-aaHouseboats.Travel-Guide-Accommodation) - [Guest Houses in Caroline County ](https://expedia.ca/Caroline-County-Guest-Houses.d553248635976434148-aaGuestHouses.Travel-Guide-Accommodation) - [Lodges in Caroline County ](https://expedia.ca/Caroline-County-Lodges.d553248635976434148-aaLodges.Travel-Guide-Accommodation) - [Resorts in Caroline County ](https://expedia.ca/Caroline-County-Resort-Hotels.d553248635976434148-aaResortHotels.Travel-Guide-Accommodation)