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

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.

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 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.

3. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

￥30,189

￥37,526 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

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

5. Best Western Kent Narrows Inn

Grasonville

Beth

￥17,037

￥18,911 total

includes taxes & fees

Oct 13 - Oct 14

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

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.

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

￥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 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

￥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 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.

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 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.

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

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

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

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.

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 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.

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

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

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

14. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

￥17,364

￥19,795 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.

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.

15. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

￥21,333

￥23,466 total

includes taxes & fees

Oct 11 - Oct 12

A gym with exercise equipment, a mirror, and a blue wall.

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

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

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

16. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

￥40,118

￥45,734 total

includes taxes & fees

Oct 12 - Oct 13

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 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 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.

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

18. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

￥81,008

￥89,108 total

includes taxes & fees

Nov 3 - Nov 4

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

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.

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

19. The Wildset

Downtown St. Michaels

Sarah

￥36,161

￥43,725 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 with a brick facade, multiple parking spaces, and a landscaped area with trees.

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

Lori

￥20,363

￥22,398 total

includes taxes & fees

Oct 7 - Oct 8

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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. 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. 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. Fairfield Inn & Suites by Marriott Easton

16. Annapolis Waterfront Hotel, Autograph Collection

17. SpringHill Suites by Marriott Annapolis

18. Inn at Perry Cabin

19. The Wildset

20. Best Western Plus Easton Inn & Suites

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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