Caroline County Holiday Rentals

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Top Holiday Rentals Destinations in Caroline County

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

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

9.6 out of 10, Exceptional, (120)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (15)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is NZ$615
includes taxes & fees
29 Sept - 30 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cass-N-Reel Luxury Houseboat
Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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

9.8 out of 10, Exceptional, (187)
"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
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (258)
"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
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Outdoor pool

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
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 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."
Dollhouse in Central Historic St Michaels
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool

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

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

10.0 out of 10, Exceptional, (49)
"We had a wonderful weekend get away. Location is perfect to take advantage of the main restaurants and shopping in St. Michael’s."
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Captain's Quarters
Fridge, microwave, oven, stovetop

Captain's Quarters

9.8 out of 10, Exceptional, (99)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Marina

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

10.0 out of 10, Exceptional, (93)
"Beautiful home in a quiet community. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Private beach

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
Poe Themed Home Close to Beaches and DE Turf
Outdoor dining

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. "
The price is NZ$482
includes taxes & fees
29 Sept - 30 Sept
Poe Themed Home Close to Beaches and DE Turf
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

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

9.6 out of 10, Exceptional, (124)
"We had a wonderful stay. This was our second time staying here and we loved it. Very quay, cozy and clean. Everything as advertised. Location is perfect as it is a very walkable town. This place is right in the middle. The owner was very friendly, open and communicative. And I had a big surprise when we returned. My neck pillow I had forgotten and left it 2 years ago was still there sitting in a closet. We hope to return next year. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Thorneton Point Estate
Interior

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

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

9.6 out of 10, Exceptional, (143)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

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

10.0 out of 10, Exceptional, (11)
"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!
Dining

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

10.0 out of 10, Exceptional, (25)
"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!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

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
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Great location and rooms. Great place!"
Ana 3-night trip
Posted 3 days ago
Hyatt Place Kent Narrows & Marina

Find out more about Caroline County

Find out more about Caroline County

Everything you need to know about Caroline County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Caroline County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Caroline County holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Caroline County holiday rentals we have selected for you start as low as NZ$482 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 holiday 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 holiday.

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.