Vacation Rentals in Caroline County

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Top Vacation Rentals in Caroline County

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (121)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (41)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (259)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (188)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (26)
"Nice stay… good family home…. Lots of sleeping accommodations…. A few steps from the beach!!!!! Great host!!!!!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

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

10.0 out of 10, Exceptional, (95)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (55)
"Great location. House is old and therefore a little quirky, but overall comfortable. "
Dollhouse in Central Historic St Michaels

Harbor View Suite Talbot County License Number STRN-25-58

10.0 out of 10, Exceptional, (31)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite Talbot County License Number STRN-25-58

Grandma's Cottage Milford Delaware

10.0 out of 10, Exceptional, (109)
"Born and raised in this area. Just back to visit friends and family. Staying at grandmas cottage felt like just that. Thanks. "
Grandma's Cottage Milford Delaware

Poe Themed Home Close to Beaches and DE Turf

10.0 out of 10, Exceptional, (4)
"Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. "
$271 nightly
The price is $278
Oct 12 - Oct 13
Total with taxes and fees
Poe Themed Home Close to Beaches and DE Turf

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

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

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

10.0 out of 10, Exceptional, (16)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Captain's Quarters

9.8 out of 10, Exceptional, (100)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters

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

9.8 out of 10, Exceptional, (43)
"Wonderful home in excellent location!!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

9.8 out of 10, Exceptional, (132)
"I booked this house for the property, the backyard, the dock, and it didn't disappoint. It's also about 20 mins from the main town (Cambridge) which was exactly what we wanted - a break from crowds and the bustle. We had such a relaxing few days just reading, fishing from the dock, and kayaking. We were four people, but this would easily fit two families. A wonderful stay overall."
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (9)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (36)
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely...
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
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

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 $278 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.