Vacation Rentals in Caroline County

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Top Cities in Caroline County

Top Vacation Rentals in Caroline County

Cass-N-Reel Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 1 - Dec 2
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

Cozy cottage on the Miller farm.

Milford
10.0 out of 10, Exceptional, (240)
"We’ve stayed here several timesWe always feel welcome and the cottage is perfect!!"
United States
Ron F.
Cozy cottage on the Miller farm.

Captain's Quarters

Frederica
9.8 out of 10, Exceptional, (103)
"Great communication, the house was extremely well equipped, very short walk to the beach. Perfect place to sit & unwind."
United States
Joseph L.
Captain's Quarters

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Delaware Turf Bungalow’s Sister!

Milford
10.0 out of 10, Exceptional, (2)
"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...
United States
Christina T.
Delaware Turf Bungalow’s Sister!

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels
9.8 out of 10, Exceptional, (56)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sherwood
10.0 out of 10, Exceptional, (20)
"Fantastic property"
United States
Harvey W.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Waterfront! Private Dock, Boat Tie-Up & Near Town

Rock Hall
10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town

Cass-Away Luxury Houseboat

Grasonville
10.0 out of 10, Exceptional, (104)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (264)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
9.6 out of 10, Exceptional, (125)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Rock Hall
10.0 out of 10, Exceptional, (73)
"This trip was a girls get away & we thoroughly enjoyed ourselves .. the house was by far the best I’ve ever rented .. clean, well appointed, & decor was gorgeous … the owner was so attentive & acted on anything we needed right away .. I highly recommend this property & we will definitely be returning …"
United States
Denise O.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge
9.8 out of 10, Exceptional, (133)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak
10.0 out of 10, Exceptional, (90)
"5 out of 5. Beautiful, well kept property across aspects. Comfortably accommodated our group of 14. Excellent communication with the Renter and felt as though we were borrowing the property from a family friend. Would recommend to anyone!"
United States
Katie M.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton
10.0 out of 10, Exceptional, (95)
"Gorgeous views and surroundings"
United States
Robin P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
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.

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Top Caroline County Hotel Reviews

Find out more about Caroline County

Discover your perfect Caroline County vacation rental with Expedia

How many vacation rentals are available in Caroline County?


Expedia has plenty of vacation rentals to choose from in and around  Caroline County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Caroline County?


The selection of Caroline County vacation rentals we have selected for you start as low as $159 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Caroline County?


Vacation rentals in Caroline County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Caroline County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Caroline County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Caroline County?


Find vacation rentals in Caroline County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Caroline County.  


What amenities are available in a vacation rental in Caroline County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Caroline County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Caroline County?   


Everytime is a great time to head to Caroline County! Staying in a Caroline County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Caroline County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Caroline County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Caroline County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Caroline County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.