Find Vacation Homes in Caroline County, MD from $345

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Top Cities in Caroline County

Vacation Homes in Caroline County

Charming 3-bedroom Ranch in delightful Dover with AC

Dover
Charming 3-bedroom Ranch in delightful Dover with AC

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (19)
"Great well-furnished townhouse in a great location and a super responsive host. What’s not to like?!?!"
United States
Lynn
$325 nightly
The price is $345
Nov 18 - Nov 19
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy cottage on the Miller farm.

Milford
10.0 out of 10, Exceptional, (237)
"Awesome place. "
United States
Michael D.
Cozy cottage on the Miller farm.

Captain's Quarters

Frederica
9.8 out of 10, Exceptional, (102)
"This house is a really nice hidden gem in a hidden gem town. The house is equipped with all that you need to have a great time on vacation. Bikes, beach chairs, corn hole, kids sand toys, well stocked kitchen. This place is a gem!"
United States
Walter H.
Captain's Quarters

Walk to Everything House

Saint Michaels
10.0 out of 10, Exceptional, (83)
"Family of four stay for 4 nights. The place is clean with all the amenities. Comfortable beds & kitchen with washer & dryer. Early American decor gave a touch of class. We enjoyed the short walk to all the shops & restaurants in St Michael’s."
United States
Corey K.
Walk to Everything House

Waterfront Estate w Private Pier, Game Room & Bar

Centreville
9.6 out of 10, Exceptional, (34)
"We take a family vacation every year and this was so perfect! Great for the kids. "
United States
Juanita M.
Waterfront Estate w Private Pier, Game Room & Bar

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Frederica
9.4 out of 10, Exceptional, (3)
"We stayed over the July 4th weekend - the property is small but set up great. The screened in porch and the hot tub was awesome! The town is super friendly and welcoming. Would stay here again!"
United States
Richard D.
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

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

Frederica
10.0 out of 10, Exceptional, (27)
"Loved the house and location. We loved being close to a quiet beach area. The local restaurant was the best food we had on the trip. The host was easy to work with and great at communication. We would stay again! "
United States
Janova L.
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Heated pool, sandy beach, pier, and playground set punch point apart!

Sherwood
10.0 out of 10, Exceptional, (11)
"We had a wonderful time. The home was perfect. There were so many areas in the home to keep both the children and adults happy. The kitchen was amazing. The owner was very helpful. We would definitely enjoy renting with them again."
United States
Adrienne N.
Heated pool, sandy beach, pier, and playground set punch point apart!

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

Tilghman
10.0 out of 10, Exceptional, (10)
"We were looking for a relaxing vacation spot for the week and this place exceeded our expectations! The property itself is beautiful and spacious. We loved being in the pool and watching the boats go by. The property manager also had attentive communication with us. Overall, it was a great stay and we would certainly recommend the place to anyone, and hopefully stay again for ourselves. "
United States
Kimberly R.
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

Charming Waterfront Stay close to St. Michaels

Easton
9.8 out of 10, Exceptional, (14)
"We had a wonderful time. The house was just perfect. "
United States
Gail M.
Charming Waterfront Stay close to St. Michaels

Escape with family or friends to this peaceful, 4-bedroom retreat on the water

2.0 star property
Cambridge
10.0 out of 10, Exceptional, (8)
"We spent a lovely week on Lee Creek. The house is far enough from Cambridge to feel like country but close enough to easily access restaurants, groceries etc. Easy biking from the house and short drive to Underground Railroad Museum and Blackwater. The house is well stocked and is very dog and kid friendly. "
United States
Danielle D.
Escape with family or friends to this peaceful, 4-bedroom retreat on the water

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Chestertown
10.0 out of 10, Exceptional, (84)
"Loved our stay!"
United States
Shaun S.
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Easton
10.0 out of 10, Exceptional, (11)
"Great property for a family summer vacation and to just relax by the pool, kayak, fish off the dock, and head to town for ice cream or crabs."
United States
Anonymous traveler
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Tranquil Delmar Home ~ 7 Mi to Salisbury!

Delmar
9.2 out of 10, Wonderful, (15)
"We absolutely enjoyed staying at this property. Clean and easy to get to the places we wanted to go. Would recommend as a great place to stay!"
United States
Christopher
Tranquil Delmar Home ~ 7 Mi to Salisbury!

Luxury Treehouse with Large Deck

Harrington
10.0 out of 10, Exceptional, (12)
"This is a place that I we can’t wait to go back to!! Everything was so unique and done up with thought. You have to go and read the beautiful story behind the “Tree House” "
United States
Debra
Luxury Treehouse with Large Deck

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

Sherwood
10.0 out of 10, Exceptional, (19)
"Gorgeous views and location. "
United States
Ryan D.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

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

Cambridge
9.8 out of 10, Exceptional, (133)
"Beautiful property with gorgeous view. The owner was helpful and accommodating. Everything was clean and the amenities were superb. An evening of kayaking on the water was amazing. Great location for the half Ironman as well! "
United States
Lynn R.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

RELAX- Eastern Shore Creek Home - 6 Guests

Grasonville
10.0 out of 10, Exceptional, (5)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests

Dollhouse in Central Historic St Michaels

St Michaels
9.8 out of 10, Exceptional, (56)
"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."
United States
Michael L.
Dollhouse in Central Historic St Michaels
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Caroline County Hotel Reviews

Find out more about Caroline County

Booking Tips to Find the Best Caroline County Vacation Homes


How much does it cost to rent a vacation home in Caroline County?

You can find incredible Caroline County vacation homes for all types of budgets: between $345 and $345 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Caroline County?

If you are looking for a great deal on your vacation home in Caroline County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Caroline County?

There are 316 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Caroline County?

Begin by entering your trip dates to see what type of Caroline County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Caroline County?

Booking Caroline County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Caroline County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Caroline County along with your vacation property, into a Caroline County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Caroline County Vacation Homes information

Number of reviews
855
Accommodation
316 Vacation Homes
Lowest Price
$345
Highest Price
$345

Explore a world of travel with Expedia