The 10 Best 4 Star Hotels in Kent Island - 2026 Updated Prices

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

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Our top choices for Kent Island 4-star hotels

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

1. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

£83

includes taxes & fees

1 Nov - 2 Nov

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

2. Graduate by Hilton Annapolis

Annapolis

Nadine

£133

includes taxes & fees

11 Nov - 12 Nov

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

A modern bar area with a long counter and multiple bar stools.

3. Rod 'N' Reel Resort

Chesapeake Beach

Pam

£110

includes taxes & fees

28 Oct - 29 Oct

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

4. The Westin Annapolis

Annapolis

Bobbi

£171

includes taxes & fees

25 Oct - 26 Oct

A balcony with a table set for two, overlooking a marina with boats.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

A waterfront area with boats docked, a clear sky, and buildings in the background.

5. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

£190

includes taxes & fees

1 Nov - 2 Nov

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

6. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

£198

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

A wooden console table with framed floral artwork, two lamps, and two ottomans.

A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

7. The Oaks Waterfront

Easton

Jeffrey

£362

includes taxes & fees

31 Oct - 1 Nov

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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Kent Island.

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

£401

11 Nov - 12 Nov

includes taxes & fees

9.6/10 Exceptional! (407 reviews)

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD

£253

3 Nov - 4 Nov

includes taxes & fees

9.6/10 Exceptional! (20 reviews)

Inn at 202 Dover

202 East Dover Street Easton MD

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Pool Spa Hot tub Breakfast included Waterpark

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.

Learn more about Kent Island

Cross the Chesapeake Bay Bridge to discover Kent Island's scenic waterfront and fresh seafood restaurants. Kayak through tranquil creeks, cycle the Cross Island Trail, or visit historic Stevensville for a taste of Eastern Shore charm.

See all hotels in Kent Island

Top Kent Island Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Esperaba mas de este hotel. Aun asi no esta mal."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Wonderful staff! Had a problem getting into the bed because it was too high and I was too short. They were wonderful with accommodating my needs! They moved me to a new room and location!"

Rod 'N' Reel Resort

10/10 Excellent

"Loved the balcony."

Find out more about Kent Island

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Compare and book 4 Star hotels in Kent Island, Maryland

Change your mind

Treat yourself

Be picky

Check availability on Kent Island 4 Star Hotels

Our top choices for Kent Island 4-star hotels

1. DoubleTree by Hilton Hotel Annapolis

2. Graduate by Hilton Annapolis

3. Rod 'N' Reel Resort

4. The Westin Annapolis

5. Annapolis Waterfront Hotel, Autograph Collection

6. The Inn at Chesapeake Bay Beach Club

7. The Oaks Waterfront

Explore similar 5-star hotels

Inn at Perry Cabin

The Inn at Tacaro Estate

Inn at 202 Dover

Learn more about Kent Island

Top Kent Island Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

Annapolis Waterfront Hotel, Autograph Collection

The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

Find out more about Kent Island

Explore a world of travel with Expedia