Top 10 Hotels in Chester, MD from ￥14,620 - Competitive Prices

A boat docked at a pier during twilight with a city skyline in the background.

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

Next weekend

In two weeks

Our top choices for Chester hotels

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.

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

1. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

￥26,735

￥29,676 total

includes taxes & fees

Sep 8 - Sep 9

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 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 swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

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

Grasonville

Betty

￥19,691

￥21,857 total

includes taxes & fees

Sep 28 - Sep 29

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

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

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.

3. Hilton Garden Inn Kent Island Marina

Grasonville

roney

￥26,937

￥29,901 total

includes taxes & fees

Sep 1 - Sep 2

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

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

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

4. Best Western Kent Narrows Inn

Grasonville

Eliezer

￥18,623

￥20,672 total

includes taxes & fees

Sep 28 - Sep 29

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

5. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

￥34,785

￥42,684 total

includes taxes & fees

Sep 28 - Sep 29

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 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

Faezeh

￥16,009

￥17,769 total

includes taxes & fees

Sep 28 - Sep 29

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

Margaret

￥25,907

￥34,208 total

includes taxes & fees

Sep 22 - Sep 23

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

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

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.

8. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

￥17,145

￥19,545 total

includes taxes & fees

Sep 13 - Sep 14

A multi-story hotel with a brick facade, large windows, and an American flag.

A pool area with a hot tub, lounge chairs, and a no diving sign.

A modern hotel lobby with a sectional sofa, armchairs, a coffee table, and a chandelier.

A gym with multiple treadmills and elliptical machines.

9. Crowne Plaza Annapolis by IHG

Annapolis

Heather

￥15,529

￥17,703 total

includes taxes & fees

Sep 13 - Sep 14

A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

10. Courtyard by Marriott Annapolis

Annapolis

Phyllis

￥15,369

￥17,521 total

includes taxes & fees

Sep 7 - Sep 8

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

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

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.

11. St Michaels Inn

St. Michaels

Karen

￥13,693

￥15,062 total

includes taxes & fees

Aug 31 - Sep 1

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

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.

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

12. DoubleTree by Hilton Hotel Annapolis

Annapolis

Fabiana

￥15,622

￥17,808 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.

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

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.

13. Fairfield Inn & Suites by Marriott Easton

Easton

Stephanie

￥21,636

￥23,800 total

includes taxes & fees

Sep 3 - Sep 4

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

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.

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

Annapolis

Leslie

￥15,241

￥17,375 total

includes taxes & fees

Sep 27 - Sep 28

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

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

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

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

15. Best Western Annapolis

Annapolis

George

￥12,825

￥14,620 total

includes taxes & fees

Sep 13 - Sep 14

16. Village Inn Annapolis MD

Annapolis

Stephen

￥13,287

￥15,148 total

includes taxes & fees

Aug 31 - Sep 1

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

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

A marina with multiple boats docked during sunset.

A historic brick building with a red roof, multiple windows, and a central staircase.

17. Historic Inns of Annapolis

Historic District

Stephanie

￥16,948

￥24,796 total

includes taxes & fees

Sep 29 - Sep 30

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 hotel lobby with a fireplace, seating area, and a television mounted on the wall.

A fitness center with exercise equipment, a wall-mounted TV, and a sign listing rules.

18. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Frank

￥15,689

￥17,885 total

includes taxes & fees

Sep 27 - Sep 28

A hotel room with two beds, a desk, a TV, and a window with curtains.

A building with a sign reading "EcoLodge."

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

A covered corridor with a series of doors, each marked with a number.

19. Econo Lodge Easton Route 50

Easton

Nicole

￥12,966

￥14,263 total

includes taxes & fees

Sep 6 - Sep 7

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

20. Best Western Plus Easton Inn & Suites

Easton

Margaret

￥20,652

￥22,717 total

includes taxes & fees

Sep 28 - Sep 29

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

Sonesta ES Suites Annapolis

8/10 Good

"It is an older hotel, but clean. Breakfast was great! They have a good size pool, volleyball court, and basketball hoop. Rooms were very comfy and big. Great for families."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Had a great stay. Check in was easy, room was clean, bed was comfortable and the cookies were great."

Historic Inns of Annapolis

8/10 Good

"Great location and close to shops and restaurants. Very quiet/comfortable room with all the amenities and coffee available in the morning. Would definitely stay here again!"

Best Western Kent Narrows Inn

8/10 Good

"Location was great, beds were comfortable and the room was clean."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"Lovely room, clean, comfortable, well appointed & quiet. We’d be happy to stay longer in such a nice room! We asked for early check-in, & were told we’d be contacted when the room was ready, but there was no follow-up contact. Our morning shower had no hot water so we washed quickly! We knew there was ongoing work with the water supply but didn’t expect cold showers. When we reported the issue at the front desk, we were graciously offered breakfast at the on-site restaurant. So glad we accepted! Food (& service & view) were excellent. We didn’t consider the restaurant previously because there was no evidence of it aside from a sign on the door. A posted menu could help. It’s a long walk down a cold hallway and we totally would have not considered it as a breakfast option. Definitely recommend eating at the restaurant!"

St Michaels Inn

8/10 Good

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Great view of the water."

The Tidewater Inn

10/10 Excellent

"We had a lovely stay at Tidewater Inn centrally located in downtown Easton within walking distance of charming shops and delicious restaurants. Our room was spacious and light filled. The bathroom was small but adequate. We ate at the restaurant in the hotel (Hunters Tavern) and had a fabulous meal. Will definitely be back."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

￥12,825

￥14,620 total

Sep 13 - Sep 14

includes taxes & fees

7.8/10 Good! (1,002 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

￥13,693

￥15,062 total

Aug 31 - Sep 1

includes taxes & fees

8/10 Very Good! (1,012 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

￥15,622

￥17,809 total

Sep 10 - Sep 11

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

￥15,689

￥17,885 total

Sep 27 - Sep 28

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

￥18,623

￥20,672 total

Sep 28 - Sep 29

includes taxes & fees

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

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

￥19,691

￥21,857 total

Sep 28 - Sep 29

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?

Cute, Cozy 2-bedroom house near Annapolis with water access: You might want to consider this vacation home rental near Chester, which offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. 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 Country Inn & Suites by Radisson, Annapolis, MD 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 Sandy Point Beach. You'll also find Queenstown Harbor Golf and Chesapeake Bay Bridge 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 ￥14,620

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. Hyatt Place Kent Narrows & Marina

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

3. Hilton Garden Inn Kent Island Marina

4. Best Western Kent Narrows Inn

5. The Inn at Chesapeake Bay Beach Club

6. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. SpringHill Suites by Marriott Annapolis

9. Crowne Plaza Annapolis by IHG

10. Courtyard by Marriott Annapolis

11. St Michaels Inn

12. DoubleTree by Hilton Hotel Annapolis

13. Fairfield Inn & Suites by Marriott Easton

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

15. Best Western Annapolis

16. Village Inn Annapolis MD

17. Historic Inns of Annapolis

18. Holiday Inn Express & Suites Annapolis by IHG

19. Econo Lodge Easton Route 50

20. Best Western Plus Easton Inn & Suites

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

DoubleTree by Hilton Hotel Annapolis

Historic Inns of Annapolis

Best Western Kent Narrows Inn

Annapolis Waterfront Hotel, Autograph Collection

St Michaels Inn

Hilton Garden Inn Annapolis Downtown

Holiday Inn Express Annapolis East-Kent Island by IHG

The Tidewater Inn

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app