Charters By Owner - Vacation Rentals in Kent County
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Luxury Places to Stay in Kent County
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Top-Rated Vacation Rentals with a Pool in Kent County
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Pet-Friendly Vacation Rentals in Kent County
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Large Vacation Homes & Villas in Kent County
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Wheelchair Accessible Vacation Homes in Kent County
Kent County Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Kent County
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About Kent County Vacation Rentals
With more than 183 Kent County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chartersbyowner and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kent County.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chartersbyowner Kent County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kent County. Places to stay near Kent County are 770.39 ft² on average, with prices averaging US $525 a night.
Chartersbyowner makes it easy and safe to find and compare vacation rentals in Kent County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Kent County
| Type | Count |
|---|---|
| Vacation Homes | 125 |
| Holiday Apartments | 21 |
| Cottages | 14 |
| Hotels | 9 |
| B&B | 4 |
| Cabin Rentals | 3 |
| Others | 1 |
| Resorts | 1 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Kent County
★ Pro Tip: Chartersbyowner makes it easy to compare the best listings on Chartersbyowner homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chartersbyowner homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kent County.
Weather in Kent County
View the weather forecast for Kent County before booking your Kent County Vacation Rentals to confirm your best time to go.
Top Attractions Around Kent County, MD
Chartersbyowner offers a large selection of top attractions around Kent County. Research things to do on your vacation before you visit Kent County.
Other Places to Stay Near Kent County, MD
Kent County Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Kent County?
There are a lot of options in Kent County. If you plan on staying in the Kent County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kent County:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Eastern Shore beach cottage get-away
- Blissful Retreat In Rock Hall
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge
- 200 steps to the beach!
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Waterfront Paradise on the Eastern Shore of Chesapeake Bay
- Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
How many vacation rentals have private pools in Kent County?
There are 4 vacation rentals with private pools near Kent County. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Kent County are best for families?
If you are looking for a family-friendly vacation home in Kent County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Kent County:
How many vacation rentals are available in Kent County?
Currently, the total number of properties listed in 2026 is over 183 in the Kent County area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kent County.
