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

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

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.

1. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

₹14,363

₹15,943 total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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.

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

Grasonville

Emily

₹11,245

₹12,482 total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

3. Hilton Garden Inn Kent Island Marina

Grasonville

roney

₹13,870

₹15,395 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

4. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

₹9,449

₹10,489 total

includes taxes & fees

28 Sept - 29 Sept

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

A lobby with a reception desk, a clock, and a wall-mounted deer head.

A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

5. Best Western Kent Narrows Inn

Grasonville

Joshua

₹10,992

₹12,201 total

includes taxes & fees

28 Sept - 29 Sept

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

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

₹18,072

₹22,463 total

includes taxes & fees

8 Sept - 9 Sept

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

A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

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

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

7. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

₹11,906

₹13,573 total

includes taxes & fees

8 Sept - 9 Sept

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

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.

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

8. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

₹10,394

₹11,849 total

includes taxes & fees

8 Sept - 9 Sept

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.

9. Kent Island Resort

Stevensville

Margaret

₹13,860

₹18,566 total

includes taxes & fees

21 Sept - 22 Sept

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

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

10. DoubleTree by Hilton Hotel Annapolis

Annapolis

Chereis

₹7,837

₹8,935 total

includes taxes & fees

27 Sept - 28 Sept

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

A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

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

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

Annapolis

Leslie

₹8,996

₹10,255 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

A breakfast bar with labeled sections for cereal and fruit, a kettle, and condiments.

12. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Harold

₹9,544

₹10,880 total

includes taxes & fees

8 Sept - 9 Sept

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

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

13. Historic Inns of Annapolis

Historic District

Amy

₹10,004

₹14,636 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

14. Courtyard by Marriott Annapolis

Annapolis

Phyllis

₹9,449

₹10,772 total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel dining area with a long table, four chairs, and three pendant lights.

A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

15. Hampton Inn Easton

Easton

Rachel

₹14,605

₹16,065 total

includes taxes & fees

1 Oct - 2 Oct

16. Village Inn Annapolis MD

Annapolis

Stephen

₹7,843

₹8,941 total

includes taxes & fees

8 Sept - 9 Sept

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

A gym with treadmills, elliptical machines, and exercise balls.

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

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

17. Best Western Annapolis

Annapolis

George

₹7,144

₹8,144 total

includes taxes & fees

27 Sept - 28 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 store with shelves of beverages, a counter with a cash register, and baskets with items.

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

18. The Westin Annapolis

Annapolis

susan greco

₹16,914

₹19,282 total

includes taxes & fees

13 Sept - 14 Sept

A hotel room with two beds, a desk, a TV, and a window with curtains.

A covered corridor with a series of doors, each marked with a number.

A hotel reception area with a check-in counter, a digital display, and a red carpet with the hotel's name.

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

19. Econo Lodge Easton Route 50

Easton

Nicole

₹7,653

₹8,418 total

includes taxes & fees

13 Sept - 14 Sept

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

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

20. Hilton Garden Inn Annapolis Downtown

Annapolis

Jeffrey

₹10,570

₹12,050 total

includes taxes & fees

7 Sept - 8 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

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Great location, very clean and staff were welcoming and helpful!"

Historic Inns of Annapolis

8/10 Good

"I liked the archaeological displays and the historically preserved property. The room was very comfortable. Some of the front desk staff were not very friendly. Some of the parking attendants were often seen glued to their cell phones rather than offering assistance. The valet online service was inconvenient and too expensive. I wanted to leave an online gratuity but did not like the convenience fee charged!"

Sonesta ES Suites Annapolis

10/10 Excellent

"Outstanding and affordable place to stay in Annapolis Maryland we go to visit our son at the naval academy it is the only place we consider stayong"

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"..........................."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Rooms kept very clean and comfortable. Staff excellent, extremely friendly and helpful. Food very good and good portions."

The Wildset

10/10 Excellent

"Clean and comfortable. All staff were friendly and helpful. Location made virtually the whole town walkable. Dinner at the restaurant was top notch."

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"My third stay. Hotel is clean, staff are friendly and helpful and the location is great."

Inn at Perry Cabin

10/10 Excellent

"All staff were very pleasant, engaged, and helpful. Everyone seems to genuinely care about making the experience memorable. The property, setting, grounds, and amenities are beautiful and well-maintained."

Best Western Annapolis

10/10 Excellent

"Clean room."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

₹7,144

₹8,144 total

27 Sept - 28 Sept

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

₹8,304

₹9,135 total

7 Sept - 8 Sept

includes taxes & fees

Quality Inn Grasonville near Kent Island

101 Vfw Ave Grasonville MD

₹9,449

₹10,489 total

28 Sept - 29 Sept

includes taxes & fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

₹9,221

₹10,511 total

10 Sept - 11 Sept

includes taxes & fees

8.2/10 Very good! (1,009 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

₹9,544

₹10,880 total

8 Sept - 9 Sept

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

₹10,992

₹12,201 total

28 Sept - 29 Sept

includes taxes & fees

8/10 Very good! (1,002 reviews)

Frequently asked questions

What's the best place to stay in Chester?

Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Graduate by Hilton Annapolis and DoubleTree by Hilton Hotel Annapolis. 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. Features 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 Love Point State Park. 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.

Explore a world of travel with Expedia

Book Hotels in Chester on Expedia.com

Chester Hotels from ₹8,144

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. Hyatt Place Kent Narrows & Marina

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

3. Hilton Garden Inn Kent Island Marina

4. Quality Inn Grasonville near Kent Island

5. Best Western Kent Narrows Inn

6. The Inn at Chesapeake Bay Beach Club

7. SpringHill Suites by Marriott Annapolis

8. Crowne Plaza Annapolis by IHG

9. Kent Island Resort

10. DoubleTree by Hilton Hotel Annapolis

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

12. Holiday Inn Express & Suites Annapolis by IHG

13. Historic Inns of Annapolis

14. Courtyard by Marriott Annapolis

15. Hampton Inn Easton

16. Village Inn Annapolis MD

17. Best Western Annapolis

18. The Westin Annapolis

19. Econo Lodge Easton Route 50

20. Hilton Garden Inn Annapolis Downtown

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Hyatt Place Kent Narrows & Marina

Historic Inns of Annapolis

Sonesta ES Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

The Wildset

Holiday Inn Express Annapolis East-Kent Island by IHG

Inn at Perry Cabin

Best Western Annapolis

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Quality Inn Grasonville near Kent Island

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Frequently asked questions

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