Top Vacation Homes in Kent County in 2026

A coastal town with a marina, a bridge, and a highway.

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Our top choices for Kent County vacation homes

A modern living room with a staircase, a dining area, and a kitchen in the background.

1. Hudson house

Canton

Thelma

A bed with white and blue pillows, a tufted headboard, and three framed botanical prints on the wall.

2. Bohemia Manor Farm

Chesapeake City

NT$12,162 total

includes taxes & fees

Sep 21 - Sep 22

A bedroom with a bed, a dresser, a mirror, a hanging light fixture, and a door.

3. Kent Island Getaway with Fire Pit Near Annapolis

Stevensville

A modern kitchen with dark cabinets, stainless steel appliances, granite countertops, and a central island.

4. Relaxing Ranch With 1 King and 2 Queens Fast Wifi

Bear

A family of three at a round metal table with a plate of food, seated outside a house with a corrugated metal wall.

5. Downtown Flat Walk to Dining Shops Sleeps 4

Downtown St. Michaels

A spacious living room with a large sliding glass door leading to a deck, a fireplace, and a dining area with a view of greenery.

6. Waterfront Kent Island Retreat 5BR Sleeps 12 Near Weddings Annapolis

Stevensville

7. Entire Home - Work From Home Ready

Hollins Market

A swimming pool with clear blue water, surrounded by lounge chairs and a covered seating area.

8. Top Floor Master Suite Bay View

North East

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Top Kent County Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"I loved the free shuttle within 5 miles. It was so great to be dropped off at my conference downtown and not have to worry about parking. They picked me up within 10-15 minutes anytime I called. The restaurant was nice and the food was very good. I loved the location."

Historic Inns of Annapolis

8/10 Good

"The best thing about this hotel is the location. Right behind it is the historic charm. It’s one of the best in the country. The staff was very helpful. The room was spacious. The room was clean. The only thing it needed was newer television monitors. We were trying to watch the U.S. Open tennis and it was hard to follow the ball. Overall, excellent."