Top 10 Hotels in Chester, MD from ￥13,951 - Competitive Prices

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Chester

Pet friendly

Pool

Apartment

Spa

Condo

Hot tub

Family friendly

Waterpark

Cottage

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chester hotels

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 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 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

￥17,417

￥19,333 total

includes taxes & fees

Oct 25 - Oct 26

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

Joseph

￥24,068

￥26,716 total

includes taxes & fees

Oct 20 - Oct 21

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 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.

3. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

￥32,362

￥39,958 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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.

4. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

￥21,943

￥24,356 total

includes taxes & fees

Oct 20 - Oct 21

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

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

A reception desk with a clock, framed pictures, and a sign for express checkout.

5. Best Western Kent Narrows Inn

Grasonville

Wesley

￥14,232

￥15,798 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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.

6. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

￥14,301

￥15,874 total

includes taxes & fees

Nov 8 - Nov 9

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.

7. Kent Island Resort

Stevensville

Bethany

￥19,375

￥26,740 total

includes taxes & fees

Oct 29 - Oct 30

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

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.

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

8. Historic Inns of Annapolis

Historic District

Ashley

￥13,567

￥20,881 total

includes taxes & fees

Oct 21 - Oct 22

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

￥16,749

￥19,094 total

includes taxes & fees

Oct 18 - Oct 19

A balcony with a table set for two, overlooking a marina with boats.

A waterfront area with boats docked, a clear sky, and buildings in the background.

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.

10. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

￥35,341

￥40,288 total

includes taxes & fees

Nov 2 - Nov 3

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

A store with shelves of beverages, a counter with a cash register, and baskets with items.

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

￥31,510

￥35,921 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

12. Graduate by Hilton Annapolis

Annapolis

Mark

￥23,285

￥26,545 total

includes taxes & fees

Oct 26 - Oct 27

A modern bathroom with a toilet, sink, and shower curtain.

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.

13. Crowne Plaza Annapolis by IHG

Annapolis

Jose

￥17,417

￥19,855 total

includes taxes & fees

Oct 25 - Oct 26

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

A buffet with labeled trays of turkey sausage and cookies.

14. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

￥15,992

￥18,231 total

includes taxes & fees

Oct 18 - Oct 19

A hotel room with two beds, a flat-screen TV, a painting, and a desk with a lamp.

15. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

￥16,749

￥19,094 total

includes taxes & fees

Oct 25 - Oct 26

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

A hotel with a covered entrance, multiple floors, and a parking lot.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

16. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

￥21,400

￥23,540 total

includes taxes & fees

Oct 18 - Oct 19

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

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

17. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

￥18,842

￥21,480 total

includes taxes & fees

Nov 1 - Nov 2

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

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

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.

18. The Wildset

Downtown St. Michaels

Sarah

￥36,260

￥43,845 total

includes taxes & fees

Nov 3 - Nov 4

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

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

A golf course with a water hazard and surrounding trees.

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

19. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

￥84,238

￥92,661 total

includes taxes & fees

Nov 3 - Nov 4

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

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.

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.

20. Best Western Plus Easton Inn & Suites

Easton

Donna

￥20,426

￥22,469 total

includes taxes & fees

Oct 18 - Oct 19

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at 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

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"Clean room!"

Historic Inns of Annapolis

10/10 Excellent

"Great location."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Clean room. Great breakfast."

Best Western Annapolis

8/10 Good

"Noisy balcony"

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."

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"We stay here frequently. The best hotel in a great location."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

More cheap stays in Chester

St Michaels Inn

1228 S Talbot Street St. Michaels MD

￥12,683

￥13,951 total

Nov 1 - Nov 2

includes taxes & fees

8/10 Very Good! (1,000 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

￥12,541

￥14,297 total

Oct 20 - Oct 21

includes taxes & fees

7.8/10 Good! (1,000 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

￥14,232

￥15,798 total

Nov 8 - Nov 9

includes taxes & fees

8/10 Very Good! (1,000 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

￥15,451

￥17,614 total

Oct 21 - Oct 22

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

￥15,992

￥18,231 total

Oct 18 - Oct 19

includes taxes & fees

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

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

￥20,426

￥22,469 total

Oct 18 - Oct 19

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 traveler data. Other good choices for your visit to the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.

What's the top vacation rental in Chester?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Chester vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What are some accommodations 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 with an onsite 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 accommodations 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. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.

Explore a world of travel with Expedia

Book Hotels in Chester on Expedia.com

Find hotels in Chester, MD from ￥13,951

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Property class

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. The Inn at Chesapeake Bay Beach Club

4. Hilton Garden Inn Kent Island Marina

5. Best Western Kent Narrows Inn

6. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. Historic Inns of Annapolis

9. DoubleTree by Hilton Hotel Annapolis

10. Annapolis Waterfront Hotel, Autograph Collection

11. The Westin Annapolis

12. Graduate by Hilton Annapolis

13. Crowne Plaza Annapolis by IHG

14. Holiday Inn Express & Suites Annapolis by IHG

15. Hilton Garden Inn Annapolis Downtown

16. Fairfield Inn & Suites by Marriott Easton

17. SpringHill Suites by Marriott Annapolis

18. The Wildset

19. Inn at Perry Cabin

20. Best Western Plus Easton Inn & Suites

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Holiday Inn Express & Suites Annapolis by IHG

Historic Inns of Annapolis

Crowne Plaza Annapolis by IHG

Best Western Annapolis

Hilton Garden Inn Annapolis Downtown

Annapolis Waterfront Hotel, Autograph Collection

The Inn at Chesapeake Bay Beach Club

Hyatt Place Kent Narrows & Marina

St Michaels Inn

More cheap stays in Chester

St Michaels Inn

Best Western Annapolis

Best Western Kent Narrows Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Plus Easton Inn & Suites

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app