Top 10 Hotels in Chester, MD from ￥14,416 - Competitive Prices

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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 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

￥17,364

￥19,274 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.

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.

2. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

￥23,993

￥26,633 total

includes taxes & fees

Oct 13 - Oct 14

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 spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

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

￥30,189

￥37,526 total

includes taxes & fees

Oct 19 - Oct 20

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

A kitchenette with a coffee machine, a framed picture, and a potted plant.

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

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

4. Best Western Kent Narrows Inn

Grasonville

Beth

￥17,037

￥18,911 total

includes taxes & fees

Oct 13 - Oct 14

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

5. Hilton Garden Inn Kent Island Marina

Grasonville

roney

￥21,875

￥24,281 total

includes taxes & fees

Oct 19 - Oct 20

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

6. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

￥15,154

￥16,822 total

includes taxes & fees

Nov 3 - Nov 4

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 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.

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

7. Kent Island Resort

Stevensville

Bethany

￥24,102

￥32,093 total

includes taxes & fees

Nov 4 - Nov 5

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.

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

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

8. Historic Inns of Annapolis

Historic District

Ashley

￥14,370

￥21,780 total

includes taxes & fees

Nov 4 - Nov 5

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

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

￥15,293

￥17,435 total

includes taxes & fees

Oct 12 - Oct 13

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 bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

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.

10. Graduate by Hilton Annapolis

Annapolis

Mark

￥23,169

￥26,412 total

includes taxes & fees

Oct 26 - Oct 27

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.

11. The Westin Annapolis

Annapolis

Bobbi

￥31,412

￥35,810 total

includes taxes & fees

Oct 25 - Oct 26

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 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.

12. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

￥17,364

￥19,795 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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.

13. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

￥17,999

￥20,519 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

14. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

￥17,364

￥19,795 total

includes taxes & fees

Oct 25 - Oct 26

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.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

15. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

￥40,118

￥45,734 total

includes taxes & fees

Oct 12 - Oct 13

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.

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

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

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

16. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

￥21,333

￥23,466 total

includes taxes & fees

Oct 11 - Oct 12

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

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

17. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

￥18,784

￥21,414 total

includes taxes & fees

Oct 25 - Oct 26

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

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

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.

18. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

￥81,008

￥89,108 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 pool area with multiple pools, lounge chairs, and a pool lift.

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

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

19. Best Western Plus Easton Inn & Suites

Easton

Lori

￥20,363

￥22,398 total

includes taxes & fees

Oct 7 - Oct 8

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.

20. The Wildset

Downtown St. Michaels

Sarah

￥36,161

￥43,725 total

includes taxes & fees

Nov 3 - Nov 4

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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

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."

Best Western Annapolis

8/10 Good

"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."

Sonesta ES Suites Annapolis

10/10 Excellent

"It is an excellent value for the cost!"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

￥12,645

￥14,416 total

Oct 12 - Oct 13

includes taxes & fees

7.8/10 Good! (1,005 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

￥14,064

￥15,470 total

Oct 11 - Oct 12

includes taxes & fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

￥16,056

￥18,305 total

Nov 1 - Nov 2

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

￥17,037

￥18,911 total

Oct 13 - Oct 14

includes taxes & fees

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

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

￥17,364

￥19,795 total

Oct 25 - Oct 26

includes taxes & fees

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

￥20,363

￥22,398 total

Oct 7 - Oct 8

includes taxes & fees

9.2/10 Wonderful! (1,004 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.

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Find hotels in Chester, MD from ￥14,416

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. Best Western Kent Narrows Inn

5. Hilton Garden Inn Kent Island Marina

6. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. Historic Inns of Annapolis

9. DoubleTree by Hilton Hotel Annapolis

10. Graduate by Hilton Annapolis

11. The Westin Annapolis

12. Crowne Plaza Annapolis by IHG

13. Hilton Garden Inn Annapolis Downtown

14. Holiday Inn Express & Suites Annapolis by IHG

15. Annapolis Waterfront Hotel, Autograph Collection

16. Fairfield Inn & Suites by Marriott Easton

17. SpringHill Suites by Marriott Annapolis

18. Inn at Perry Cabin

19. Best Western Plus Easton Inn & Suites

20. The Wildset

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Best Western Annapolis

Sonesta ES Suites Annapolis

St Michaels Inn

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Best Western Kent Narrows Inn

Holiday Inn Express & Suites Annapolis by IHG

Best Western Plus Easton Inn & Suites

Frequently asked questions

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