Best Chester Hotels in 2026 from HK$700 - Fully Refundable Options

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

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

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.

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

Grasonville

Marc

HK$808

HK$897 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

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

2. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

HK$1,193

HK$1,324 total

includes taxes & fees

13 Oct - 14 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

HK$1,152

HK$1,278 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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.

4. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

HK$1,501

HK$1,865 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

5. Best Western Kent Narrows Inn

Grasonville

Beth

HK$851

HK$945 total

includes taxes & fees

4 Oct - 5 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.

6. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

HK$753

HK$836 total

includes taxes & fees

1 Nov - 2 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 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.

7. Kent Island Resort

Stevensville

Bethany

HK$1,138

HK$1,527 total

includes taxes & fees

28 Oct - 29 Oct

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

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.

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

8. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

HK$705

HK$804 total

includes taxes & fees

4 Oct - 5 Oct

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.

9. Historic Inns of Annapolis

Historic District

Ashley

HK$834

HK$1,220 total

includes taxes & fees

12 Oct - 13 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 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.

10. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

HK$894

HK$1,020 total

includes taxes & fees

1 Nov - 2 Nov

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.

11. The Westin Annapolis

Annapolis

Bobbi

HK$1,561

HK$1,780 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

12. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

HK$1,091

HK$1,243 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

13. Graduate by Hilton Annapolis

Annapolis

princess

HK$1,152

HK$1,313 total

includes taxes & fees

26 Oct - 27 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 property with a docked boat, a tall building with balconies, and a church spire in the background.

14. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

HK$1,814

HK$2,068 total

includes taxes & fees

1 Nov - 2 Nov

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 hotel entrance with a covered walkway, a flag, and a landscaped area with trees.

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

15. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

HK$808

HK$921 total

includes taxes & fees

1 Nov - 2 Nov

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

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

16. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

HK$863

HK$984 total

includes taxes & fees

4 Oct - 5 Oct

A room with a view of a wooden deck and a gazebo by the water.

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

A golf course with a water hazard and surrounding trees.

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

17. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

HK$4,166

HK$4,583 total

includes taxes & fees

26 Oct - 27 Oct

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

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

18. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Imola

HK$1,059

HK$1,208 total

includes taxes & fees

27 Oct - 28 Oct

A two-story house with a porch, a front door, and a small garden area.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

19. The Wildset

Downtown St. Michaels

Sarah

HK$1,875

HK$2,259 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

Annapolis

Leslie

HK$747

HK$852 total

includes taxes & fees

25 Oct - 26 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

Historic Inns of Annapolis

10/10 Excellent

"All good. Great location and nice/clean rooms."

Sonesta ES Suites Annapolis

10/10 Excellent

"The staff was welcoming and very pleasant at check in. I was able to park my car next to my room so i did not have to walk a lot together to my room. The room and amenities at this hotel is amazing! Full kitchen! Easy accred walking path to the breakfast buffet. The breakfast was excellent with healthy choices . I enjoyed my stay!!"

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Beautiful views, great food options, and free bikes! My mom, sister and I had a great little getaway. Will be back."

Hilton Garden Inn Kent Island Marina

10/10 Excellent

"Had a good time. Nice area"

St Michaels Inn

8/10 Good

"Clean and breakfast was provided. It was in the right location that we needed for our weekend. Stay."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"Everything was perfect 👍"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Best spot at Kent Narrows."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."

Candlewood Suites Annapolis by IHG

8/10 Good

"The property was very clean and staff was friendly."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

HK$614

HK$700 total

20 Oct - 21 Oct

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

HK$699

HK$769 total

12 Oct - 13 Oct

includes taxes & fees

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

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

HK$808

HK$921 total

1 Nov - 2 Nov

includes taxes & fees

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

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

HK$851

HK$945 total

4 Oct - 5 Oct

includes taxes & fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

HK$830

HK$946 total

26 Oct - 27 Oct

includes taxes & fees

8.2/10 Very good! (1,008 reviews)

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

HK$1,012

HK$1,113 total

8 Oct - 9 Oct

includes taxes & fees

9.2/10 Wonderful! (1,009 reviews)

Hotels in Chester with star-rating

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.

What are some of the best holiday rentals that Chester has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Chester is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all 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 HK$700

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. The Inn at Chesapeake Bay Beach Club

5. Best Western Kent Narrows Inn

6. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. DoubleTree by Hilton Hotel Annapolis

9. Historic Inns of Annapolis

10. Hilton Garden Inn Annapolis Downtown

11. The Westin Annapolis

12. SpringHill Suites by Marriott Annapolis

13. Graduate by Hilton Annapolis

14. Annapolis Waterfront Hotel, Autograph Collection

15. Holiday Inn Express & Suites Annapolis by IHG

16. Crowne Plaza Annapolis by IHG

17. Inn at Perry Cabin

18. Fairfield Inn & Suites By Marriott Annapolis

19. The Wildset

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

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Historic Inns of Annapolis

Sonesta ES Suites Annapolis

The Inn at Chesapeake Bay Beach Club

Hilton Garden Inn Kent Island Marina

St Michaels Inn

Holiday Inn Express & Suites Annapolis by IHG

Hyatt Place Kent Narrows & Marina

Annapolis Waterfront Hotel, Autograph Collection

Candlewood Suites Annapolis by IHG

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Hampton Inn & Suites Annapolis

Best Western Plus Easton Inn & Suites

Hotels in Chester with star-rating

Frequently asked questions

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