Chester Hotels from €79 - Fully Refundable Options

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

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Our top choices for Chester hotels

Two Adirondack chairs facing a calm body of water with a clear sky above.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A modern food court with a central island, various food stations, and a yogurt display.

A reception desk with a modern design, a digital display, and a check-in counter.

1. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Marc

€109

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.

A restaurant with a counter, seating area, and a clock on the wall.

An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

2. Best Western Kent Narrows Inn

Grasonville

Wesley

€89

includes taxes & fees

8 Nov - 9 Nov

A patio with outdoor seating, overlooking a marina with boats.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

An indoor swimming pool with clear views of boats and water.

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

3. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

€145

includes taxes & fees

8 Nov - 9 Nov

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

An outdoor event area with round tables and a view of the water.

4. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

€151

includes taxes & fees

21 Oct - 22 Oct

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

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

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

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

5. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

€226

includes taxes & fees

2 Nov - 3 Nov

A large, two-story barn-style building with a covered front porch and a garage.

A large, two-story white house with a porch and multiple windows.

A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

6. Kent Island Resort

Stevensville

Bethany

€149

includes taxes & fees

28 Oct - 29 Oct

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A spacious lobby with a staircase, a reception desk, and a dining area.

A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

7. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

€90

includes taxes & fees

8 Nov - 9 Nov

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

A historic brick building with a red roof, multiple windows, and a central staircase.

A marina with multiple boats docked during sunset.

8. Historic Inns of Annapolis

Historic District

Ashley

€118

includes taxes & fees

21 Oct - 22 Oct

9. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

€108

includes taxes & fees

10 Nov - 11 Nov

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

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

10. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

€108

includes taxes & fees

18 Oct - 19 Oct

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

A microwave, a coffee maker, and a refrigerator in a kitchen area.

A modern office setup with two monitors, a keyboard, and two wooden chairs.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

11. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

€103

includes taxes & fees

9 Nov - 10 Nov

A two-story building with a covered entrance and an American flag.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

A hotel room with two beds, a chair, and a painting on the wall.

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

12. St Michaels Inn

St. Michaels

Lynn

€79

includes taxes & fees

1 Nov - 2 Nov

A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

A hotel room with a large bed, a desk with a laptop, a television, and a door with a curtain.

A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

A hotel lobby with a reception desk, seating area, and dining space.

13. Best Western Annapolis

Annapolis

Silvia

€81

includes taxes & fees

28 Oct - 29 Oct

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

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 modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

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

14. Graduate by Hilton Annapolis

Annapolis

Mark

€149

includes taxes & fees

26 Oct - 27 Oct

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

15. Best Western Plus Easton Inn & Suites

Easton

Donna

€127

includes taxes & fees

28 Oct - 29 Oct

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

16. Baymont by Wyndham Easton

Easton

Edwin

€88

includes taxes & fees

28 Oct - 29 Oct

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

17. Crowne Plaza Annapolis by IHG

Annapolis

Jose

€109

includes taxes & fees

11 Nov - 12 Nov

A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

A swimming pool with lounge chairs and a brick building in the background.

A hotel lobby with a reception desk, a fireplace, and a colorful rug.

A spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.

18. Hampton Inn & Suites Annapolis

Annapolis

Courtney

€99

includes taxes & fees

9 Nov - 10 Nov

A conference room with a large table, chairs, water bottles, and a flat-screen TV on the wall.

A gym with exercise equipment, including a treadmill, stationary bike, and weights.

A kitchenette with a coffee maker, a microwave, a sink, and a framed picture of a bridge.

19. Hilton Garden Inn Annapolis

Annapolis

Glenn

€94

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with tables, chairs, and a fire feature.

A bar area with a long counter, multiple stools, and a television above.

A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.

A modern lounge area with a sofa, round tables, and chairs, featuring geometric wall decor and large windows.

20. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

€137

includes taxes & fees

28 Oct - 29 Oct

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Hotels recommended for families in Chester

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

€109

includes taxes & fees

25 Oct - 26 Oct

Hyatt Place Kent Narrows & Marina

Grasonville

€151

includes taxes & fees

21 Oct - 22 Oct

Hilton Garden Inn Kent Island Marina

Grasonville

€145

includes taxes & fees

8 Nov - 9 Nov

The Inn at Chesapeake Bay Beach Club

Stevensville

€226

includes taxes & fees

2 Nov - 3 Nov

Best Western Kent Narrows Inn

Grasonville

€89

includes taxes & fees

8 Nov - 9 Nov

Quality Inn Grasonville near Kent Island

Grasonville

€90

includes taxes & fees

8 Nov - 9 Nov

Historic Inns of Annapolis

Historic District

€118

includes taxes & fees

21 Oct - 22 Oct

Hilton Garden Inn Annapolis Downtown

Annapolis

€108

includes taxes & fees

10 Nov - 11 Nov

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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

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Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester

Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Clean room. Great breakfast."

Best Western Annapolis

8/10 Good

"Noisy balcony"

Historic Inns of Annapolis

10/10 Excellent

"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."

Hilton Garden Inn Annapolis Downtown

8/10 Good

"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"all good. Very good when it comes to parking during a boat show."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation foul up."