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

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

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

Grasonville

Betty

S$172

includes taxes & fees

31 Aug - 1 Sept

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

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

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

2. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

S$236

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

3. Hilton Garden Inn Kent Island Marina

Grasonville

roney

S$207

includes taxes & fees

7 Sept - 8 Sept

A swimming pool with a mural, lounge chairs, and a hot tub.

A modern interior with a dining area, kitchen, and living space.

A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.

A patio area with lounge chairs, a table, and umbrellas.

4. Best Western Kent Narrows Inn

Grasonville

chanel

S$164

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

5. Kent Island Resort

Stevensville

Margaret

S$272

includes taxes & fees

14 Sept - 15 Sept

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

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

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.

6. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

S$303

includes taxes & fees

8 Sept - 9 Sept

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

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

7. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

S$141

includes taxes & fees

28 Sept - 29 Sept

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

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.

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

8. DoubleTree by Hilton Hotel Annapolis

Annapolis

Fabiana

S$141

includes taxes & fees

30 Aug - 31 Aug

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

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

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

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

9. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Gary

S$196

includes taxes & fees

1 Sept - 2 Sept

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

A pool area with a hot tub, lounge chairs, and a no diving sign.

A modern hotel lobby with a sectional sofa, armchairs, a coffee table, and a chandelier.

A gym with multiple treadmills and elliptical machines.

10. Crowne Plaza Annapolis by IHG

Annapolis

Heather

S$141

includes taxes & fees

13 Sept - 14 Sept

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.

11. St Michaels Inn

St. Michaels

Karen

S$120

includes taxes & fees

31 Aug - 1 Sept

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.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

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

12. Historic Inns of Annapolis

Historic District

Stephanie

S$198

includes taxes & fees

27 Sept - 28 Sept

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

A restaurant with a yellow cushioned bench, wooden tables, and chairs.

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.

13. Hilton Garden Inn Annapolis Downtown

Annapolis

Nelson

S$153

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

14. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

S$155

includes taxes & fees

13 Sept - 14 Sept

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

A hotel with a covered entrance, large columns, and a brick facade.

A hotel lobby with a fireplace, seating area, and a television mounted on the wall.

A fitness center with exercise equipment, a wall-mounted TV, and a sign listing rules.

15. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Frank

S$142

includes taxes & fees

27 Sept - 28 Sept

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

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

16. Residence Inn By Marriott Annapolis

Annapolis

Caitlin

S$196

includes taxes & fees

2 Sept - 3 Sept

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

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

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

17. The Westin Annapolis

Annapolis

susan greco

S$245

includes taxes & fees

30 Aug - 31 Aug

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

18. Courtyard by Marriott Annapolis

Annapolis

Phyllis

S$139

includes taxes & fees

7 Sept - 8 Sept

A modern lobby with a reception desk, seating area, and potted plants.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

A Hilton Garden Inn with a large building and a smaller entrance building.

A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

19. Hilton Garden Inn Annapolis

Annapolis

Glenn

S$131

includes taxes & fees

27 Sept - 28 Sept

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

A hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

A swimming pool with a tiled edge, wooden chairs, and tables around it.

20. Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Leslie

S$138

includes taxes & fees

27 Sept - 28 Sept

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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

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Location is great! Thank you."

Graduate by Hilton Annapolis

10/10 Excellent

"cccc"

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Great view of the water."

St Michaels Inn

8/10 Good

"-"

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good

"The A/C was really loud when it turned on and off. Otherwise, our stay was fine."

Sonesta ES Suites Annapolis

10/10 Excellent

"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"

The Westin Annapolis

10/10 Excellent

"Walking distance from the historic main street."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

S$116

13 Sept - 14 Sept

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

S$120

31 Aug - 1 Sept

includes taxes & fees

8/10 Very good! (1,010 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

S$142

27 Sept - 28 Sept

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

S$143

16 Sept - 17 Sept

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

S$164

28 Sept - 29 Sept

includes taxes & fees

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

S$172

31 Aug - 1 Sept

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 Country Inn & Suites by Radisson, Annapolis, MD 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 Sandy Point Beach. You'll also find Queenstown Harbor Golf and Chesapeake Bay Bridge 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. Kent Island Resort

6. The Inn at Chesapeake Bay Beach Club

7. Quality Inn Grasonville near Kent Island

8. DoubleTree by Hilton Hotel Annapolis

9. Fairfield Inn & Suites By Marriott Annapolis

10. Crowne Plaza Annapolis by IHG

11. St Michaels Inn

12. Historic Inns of Annapolis

13. Hilton Garden Inn Annapolis Downtown

14. SpringHill Suites by Marriott Annapolis

15. Holiday Inn Express & Suites Annapolis by IHG

16. Residence Inn By Marriott Annapolis

17. The Westin Annapolis

18. Courtyard by Marriott Annapolis

19. Hilton Garden Inn Annapolis

20. Country Inn & Suites by Radisson, Annapolis, MD

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Crowne Plaza Annapolis by IHG

Graduate by Hilton Annapolis

Holiday Inn Express Annapolis East-Kent Island by IHG

St Michaels Inn

Country Inn & Suites by Radisson, Annapolis, MD

Sonesta ES Suites Annapolis

The Westin Annapolis

Annapolis Waterfront Hotel, Autograph Collection

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Frequently asked questions

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