Vacation Homes in Kent County, MD
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Top cities with Vacation Homes to explore in Kent County

Chestertown
Top Vacation Homes in Kent County

Rooftop Deck Escape! Free Parking!

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

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

Beachfront Sunsets on the Water at Oakwood Beach

Charming 3-bedroom Ranch in delightful Dover with AC

Large 2 bedroom house with private parking in a nice neighborhood

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

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.

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
Find the Best Vacation Homes in Kent County
Why book a vacation home in Kent County?
Vacation homes in Kent County make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Kent County?
Private Kent County rental homes range between $278 - $1,161 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Kent County vacation home rentals. You might look for Kent County rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Kent County offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Kent County?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Kent County. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Kent County hotels and vacation homes that best suit your stay. We also have deals for flights, and Kent County car rentals. You’ll save even more when you bundle your items into a Kent County vacation package!
How many vacation homes are available to book in Kent County?
There are 979 rental homes in Kent County. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Kent County?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Kent County Vacation Homes essential information
Accommodation | 979 Vacation Homes |
|---|---|
Lowest Price | $278 |
Highest Price | $1,161 |
Popular accommodation | Rooftop Deck Escape! Free Parking!, Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Beachfront Sunsets on the Water at Oakwood Beach, Charming 3-bedroom Ranch in delightful Dover with AC, Large 2 bedroom house with private parking in a nice neighborhood, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, 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., 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, Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! ! |
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