𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester (2026)

A boat docked at a pier during twilight with a city skyline in the background.

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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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

S$149

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.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

2. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

S$216

includes taxes & fees

19 Oct - 20 Oct

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.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

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

3. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

S$197

includes taxes & fees

19 Oct - 20 Oct

A hotel room with two beds, a desk, a chair, and a bathroom.

A wooden pavilion with picnic tables and benches, a grill, and a red bench.

A poolside area with lounge chairs and a mural of a sunset over water.

4. Best Western Kent Narrows Inn

Grasonville

Wesley

S$128

includes taxes & fees

8 Nov - 9 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.

5. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

S$323

includes taxes & fees

2 Nov - 3 Nov

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

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

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

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

S$214

includes taxes & fees

28 Oct - 29 Oct

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

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

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

A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

7. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

S$128

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 marina with multiple boats docked during sunset.

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.

8. Historic Inns of Annapolis

Historic District

Ashley

S$169

includes taxes & fees

19 Oct - 20 Oct

A modern lobby with a seating area, a fireplace, and a bookshelf.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.

9. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

S$154

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

10. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

S$154

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 buffet with various food items, including omelets and baked goods, in stainless steel containers.

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

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

S$139

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

12. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

S$197

includes taxes & fees

27 Oct - 28 Oct

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

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

A multi-story hotel with a brick facade, large windows, and an American flag.

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

13. Crowne Plaza Annapolis by IHG

Annapolis

Jose

S$153

includes taxes & fees

25 Oct - 26 Oct

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

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.

A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

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

14. Best Western Plus Easton Inn & Suites

Easton

Patricia

S$182

includes taxes & fees

13 Oct - 14 Oct

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

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

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.

15. Graduate by Hilton Annapolis

Annapolis

Mark

S$214

includes taxes & fees

26 Oct - 27 Oct

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

An outdoor patio with tables and chairs, a brick floor, and a building with a green roof in the background.

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

16. Hilton Garden Inn Annapolis

Annapolis

Glenn

S$135

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

A hotel pool area with two pools, chairs, and a sunshade.

A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

A hotel reception area with a reception desk, a television, and seating area.

17. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

S$174

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A gym with treadmills, weight machines, and dumbbells.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

18. Sonesta ES Suites Annapolis

Edgewater

Philip

S$133

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

19. St Michaels Inn

St. Michaels

Lynn

S$120

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

20. Hampton Inn & Suites Annapolis

Annapolis

Courtney

S$142

includes taxes & fees

19 Oct - 20 Oct

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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.

See properties

Learn more about Chester

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

See all hotels in Chester

Top Chester Hotel Reviews

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Awesome place"

Sonesta ES Suites Annapolis

10/10 Excellent

"Shalinda was the most welcoming front desk staff i have ever encountered."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Good stay , wish the hot tub worked"

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Breakfast need to work on, it has nothing to eat then we have to go out buy breakfast. Everythingelse is good."

St Michaels Inn

10/10 Excellent

"na"

Baymont by Wyndham Easton

10/10 Excellent

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."

Hampton Inn & Suites Annapolis

8/10 Good

"Everything was great here except the plug for the tub didnt work."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"

The Westin Annapolis

10/10 Excellent

"Easy parking. Super comfy bed."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

S$116

20 Oct - 21 Oct

includes taxes & fees

7.8/10 Good! (1,007 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

S$120

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,005 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

S$128

8 Nov - 9 Nov

includes taxes & fees

8/10 Very good! (1,004 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

S$139

9 Nov - 10 Nov

includes taxes & fees

8.4/10 Very good! (1,001 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

S$142

19 Oct - 20 Oct

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

S$182

13 Oct - 14 Oct

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Located 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! You'll find that most hotel bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What are some accommodation options with pools in Chester?

Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. St Michaels Inn and Sonesta ES Suites Annapolis are a couple of other choices that offer an on-site pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the waterfront, seafood restaurants and golf courses. In Chester, there are 9 hotels and other accommodation options to choose from. Find out more about Chester.

What is there to see in Chester?

Places to visit in the wider area include Northern Chesapeake Bay, Matapeake State Park and Eastern Neck National Wildlife Refuge. You'll also find Sandy Point Beach and Queenstown Harbor Golf in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.

Chester Hotels from S$116

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

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

2. Hyatt Place Kent Narrows & Marina

3. Hilton Garden Inn Kent Island Marina

4. Best Western Kent Narrows Inn

5. The Inn at Chesapeake Bay Beach Club

6. Kent Island Resort

7. Quality Inn Grasonville near Kent Island

8. Historic Inns of Annapolis

9. Hilton Garden Inn Annapolis Downtown

10. DoubleTree by Hilton Hotel Annapolis

11. Holiday Inn Express & Suites Annapolis by IHG

12. Fairfield Inn & Suites By Marriott Annapolis

13. Crowne Plaza Annapolis by IHG

14. Best Western Plus Easton Inn & Suites

15. Graduate by Hilton Annapolis

16. Hilton Garden Inn Annapolis

17. SpringHill Suites by Marriott Annapolis

18. Sonesta ES Suites Annapolis

19. St Michaels Inn

20. Hampton Inn & Suites Annapolis

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Hyatt Place Kent Narrows & Marina

Sonesta ES Suites Annapolis

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

St Michaels Inn

Baymont by Wyndham Easton

Hampton Inn & Suites Annapolis

The Inn at Chesapeake Bay Beach Club

The Westin Annapolis

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Best Western Kent Narrows Inn

Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Best Western Plus Easton Inn & Suites

Frequently asked questions

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