Top 10 Hotels in Chester, MD from ₩115,625 - Competitive Prices

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Our top choices for Chester hotels

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

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.

1. Best Western Kent Narrows Inn

Grasonville

Joshua

₩156,068

₩173,236 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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.

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

Grasonville

jayne

₩144,059

₩159,905 total

includes taxes & fees

Oct 13 - Oct 14

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

A kitchen with a stone wall, a microwave, and various food items on the counter.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.

A residential area with a large building, a swimming pool, and well-maintained lawns.

3. Baymont by Wyndham Easton

Easton

Erik

₩131,624

₩144,787 total

includes taxes & fees

Sep 21 - Sep 22

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.

4. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

₩204,645

₩227,157 total

includes taxes & fees

Oct 4 - Oct 5

A large, two-story barn-style building with a covered front porch and a garage.

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

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.

5. Kent Island Resort

Stevensville

Bethany

₩206,113

₩274,328 total

includes taxes & fees

Oct 12 - Oct 13

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 residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

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

₩256,581

₩318,935 total

includes taxes & fees

Sep 28 - Sep 29

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 room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

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

7. Best Western Plus Easton Inn & Suites

Easton

cherie

₩173,066

₩190,373 total

includes taxes & fees

Sep 27 - Sep 28

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.

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.

8. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

₩181,317

₩199,448 total

includes taxes & fees

Sep 27 - Sep 28

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

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Chereis

₩111,276

₩126,855 total

includes taxes & fees

Sep 27 - Sep 28

A two-story building with a covered entrance and an American flag.

A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

A hotel room with two beds, a chair, and a painting on the wall.

10. St Michaels Inn

St. Michaels

Lynn

₩126,781

₩139,460 total

includes taxes & fees

Sep 16 - Sep 17

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 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.

11. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

₩134,635

₩149,445 total

includes taxes & fees

Oct 5 - Oct 6

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.

12. Econo Lodge Easton Route 50

Easton

Brady

₩108,656

₩119,522 total

includes taxes & fees

Sep 21 - Sep 22

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.

A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

13. Holiday Inn Express Easton by IHG

Easton

Alicia

₩200,606

₩220,667 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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.

14. Hilton Garden Inn Kent Island Marina

Grasonville

roney

₩170,663

₩189,436 total

includes taxes & fees

Oct 13 - Oct 14

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

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

15. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

₩169,042

₩192,708 total

includes taxes & fees

Sep 16 - Sep 17

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

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

A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

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

16. Hampton Inn Easton

Easton

Rachel

₩208,592

₩229,454 total

includes taxes & fees

Sep 27 - Sep 28

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

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

17. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

₩147,576

₩168,237 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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

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

18. Best Western Annapolis

Annapolis

George

₩101,425

₩115,625 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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.

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

Annapolis

Leslie

₩128,173

₩146,117 total

includes taxes & fees

Oct 12 - Oct 13

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A patio area with a stone fire pit, outdoor furniture, and a covered seating area.

A gym with treadmills, weight machines, and dumbbells.

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

20. Sonesta ES Suites Annapolis

Edgewater

Philip

₩128,794

₩146,825 total

includes taxes & fees

Oct 4 - Oct 5

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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

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"One thing that stands out above everything else is the staff.... friendly, helpful, professional and informative. That shuttle service was an amazing bonus to use for exploring downtown without having to find parking, drop off & pick up..."

Courtyard by Marriott Annapolis

8/10 Good

"Room was clean and staff were helpful. The breakfast was a bit disappointing. The pool was nice. The jacuzzi was underwhelming."

The Westin Annapolis

10/10 Excellent

"This is a fabulous resort! Very clean, great location and the staff is great!"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"This is a great hotel in a great location two great restaurants."

Hilton Garden Inn Annapolis Downtown

8/10 Good

"Could do better with parking it should be inclusive for handicapped people."

St Michaels Inn

8/10 Good

"The one issue was there were flies in our room and a squished bug came on our wall. There also were cobwebs in the corner. Not enough pillows and old."

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Very much enjoyed our quick one-night stay here. It was nice that there was a bar where we could watch the football game and have a drink (great bartender!). Breakfast was better than other similar places on Kent Narrows with a beautiful marina view."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Room was amazing. Staff is super friendly and helpful. Plenty of parking. Would definitely stay again."

Best Western Annapolis

10/10 Excellent

"Breakfast was really good but they never did get our door key to work properly. Room was very clean and bed was comfortable. Staff was very friendly and helpful but the outside of the rooms, such as doors needs serious upgrades."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

₩101,425

₩115,625 total

Sep 27 - Sep 28

includes taxes & fees

7.8/10 Good! (1,006 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

₩126,781

₩139,460 total

Sep 16 - Sep 17

includes taxes & fees

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

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

₩130,913

₩149,241 total

Sep 24 - Sep 25

includes taxes & fees

8.2/10 Very Good! (1,002 reviews)

Quality Inn Grasonville near Kent Island

101 Vfw Ave Grasonville MD

₩134,635

₩149,445 total

Oct 5 - Oct 6

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

₩135,502

₩154,472 total

Sep 27 - Sep 28

includes taxes & fees

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

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

₩156,068

₩173,236 total

Sep 28 - Sep 29

includes taxes & fees

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.

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 Love Point State Park. You'll also find Eastern Neck National Wildlife Refuge and Sandy Point Beach 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 ₩115,625

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. Best Western Kent Narrows Inn

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

3. Baymont by Wyndham Easton

4. Hyatt Place Kent Narrows & Marina

5. Kent Island Resort

6. The Inn at Chesapeake Bay Beach Club

7. Best Western Plus Easton Inn & Suites

8. Fairfield Inn & Suites by Marriott Easton

9. DoubleTree by Hilton Hotel Annapolis

10. St Michaels Inn

11. Quality Inn Grasonville near Kent Island

12. Econo Lodge Easton Route 50

13. Holiday Inn Express Easton by IHG

14. Hilton Garden Inn Kent Island Marina

15. SpringHill Suites by Marriott Annapolis

16. Hampton Inn Easton

17. Crowne Plaza Annapolis by IHG

18. Best Western Annapolis

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

20. Sonesta ES Suites Annapolis

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

Courtyard by Marriott Annapolis

The Westin Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Hilton Garden Inn Annapolis Downtown

St Michaels Inn

Hyatt Place Kent Narrows & Marina

Country Inn & Suites by Radisson, Annapolis, MD

Best Western Annapolis

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Quality Inn Grasonville near Kent Island

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Frequently asked questions

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