Find Vacation Homes in Kent County, MD from $279

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Top Cities in Kent County

Vacation Homes in Kent County

Rooftop Deck Escape! Free Parking!

South Baltimore
8.4 out of 10, Very Good, (36)
"It was very nice"
United States
Cher P.
$242 nightly
The price is $279
Dec 8 - Dec 9
Total with taxes and fees
Rooftop Deck Escape! Free Parking!

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Perryville
10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (33)
"Beautiful home in a great central location for walking to most downtown and USNA destinations. "
United States
Hunter S.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Beachfront Sunsets on the Water at Oakwood Beach

Salem
10.0 out of 10, Exceptional, (44)
"Excellent property and outstanding hosts. Peaceful, relaxing, and a wonderful spot to finish out the summer. The provided amenities exceeded expectations. The house has everything needed for a home away from home vacation rental. "
United States
Craig F.
Beachfront Sunsets on the Water at Oakwood Beach

Charming 3-bedroom Ranch in delightful Dover with AC

Dover
10.0 out of 10, Exceptional, (1)
"Host was great"
United States
mark o.
Charming 3-bedroom Ranch in delightful Dover with AC

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
$287 nightly
The price is $327
Dec 8 - Dec 9
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
$1,047 nightly
The price is $1,194
Dec 9 - Dec 10
Total with taxes and fees
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Eastport
10.0 out of 10, Exceptional, (126)
"We had a great stay! The house was adorable and the pool was awesome!"
United States
Kathleen J.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Historic District
10.0 out of 10, Exceptional, (125)
"Great location, very clean house, wonderful stay"
United States
Kathryn O.
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Location is perfect and a big bonus we have our own parking at the home!

Historic District
10.0 out of 10, Exceptional, (41)
"Perfect location and parking was a big bonus!"
United States
Angela H.
Location is perfect and a big bonus we have our own parking at the home!

BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE

Upper Fells Point
9.6 out of 10, Exceptional, (8)
"Amazing property Located in a great areaWell managed and maintained Everything is close by and super safe too"
United States
Mayank G.
BEAUTIFULLY FURNISHED COZY ENSUITE 2BR3 BA IN UPPER FELLS POINT, BALTIMORE

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena
9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville
9.2 out of 10, Wonderful, (181)
"An amazing time and great family memories it simply was a delight and was very relaxing. So many things around to do. Definitely would stay again. "
United States
Stacey W.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Waterfront Oasis w/ Private Dock, 3BR/2BA

Middle River
9.4 out of 10, Exceptional, (39)
"Perfect place, close to the park and the most amazing sunset "
United States
Nicoleta E.
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

St. Michaels
9.8 out of 10, Exceptional, (45)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Crofton
9.8 out of 10, Exceptional, (101)
"Lovely place, family friendly, clean and wonderful host. Location was also a plus with a close proximity to restaurants and shops and only 20 min from Annapolis.We would definitely stay here again!"
United States
Brenda R.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

200 steps to the beach!

Rock Hall
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!

Cozy Private Family Palace near BWI, Pet-Friendly

Glen Burnie
9.8 out of 10, Exceptional, (21)
"Quiet area house was clean close to everything we needed"
United States
Kimberly S.
$339 nightly
The price is $386
Dec 8 - Dec 9
Total with taxes and fees
Cozy Private Family Palace near BWI, Pet-Friendly

Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Chesapeake City
10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Holiday Promo: Get 10% Off Holiday Stays

Centreville
9.6 out of 10, Exceptional, (35)
"Great location and plenty of fun"
United States
Carl S.
Holiday Promo: Get 10% Off Holiday Stays
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 Kent County Hotel Reviews

Find out more about Kent County

Booking Tips to Find the Best Kent County Vacation Homes


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

You can find incredible Kent County vacation homes for all types of budgets: between $279 and $1,194 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 Kent County?

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


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

There are 979 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 Kent County?

Begin by entering your trip dates to see what type of Kent 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 Kent County?

Booking Kent 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 Kent 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 Kent County along with your vacation property, into a Kent 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.

Kent County Vacation Homes information

Number of reviews
1,134
Accommodation
979 Vacation Homes
Lowest Price
$279
Highest Price
$1,194

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