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

Hotels in Chester

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Where to stay in Chester?

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

$103

$114 total

includes taxes & fees

Nov 1 - Nov 2

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

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

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

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

2. The Inn at Chesapeake Bay Beach Club

Stevensville

$191

$238 total

includes taxes & fees

Oct 19 - Oct 20

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

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

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.

3. Hilton Garden Inn Kent Island Marina

Grasonville

$139

$154 total

includes taxes & fees

Oct 19 - Oct 20

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

$152

$169 total

includes taxes & fees

Oct 13 - Oct 14

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

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.

5. Best Western Kent Narrows Inn

Grasonville

$115

$128 total

includes taxes & fees

Nov 1 - Nov 2

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

6. Quality Inn Grasonville near Kent Island

Grasonville

$96

$107 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

7. Kent Island Resort

Stevensville

$161

$213 total

includes taxes & fees

Oct 28 - Oct 29

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

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

A marina with multiple boats docked during sunset.

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

8. Historic Inns of Annapolis

Historic District

$95

$142 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor patio with tables, chairs, and a fire feature.

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

A bar area with a long counter, multiple stools, and a television above.

A modern dining area with multiple tables and chairs, large windows with a view of greenery, and decorative wall mirrors.

9. Fairfield Inn & Suites By Marriott Annapolis

Annapolis

$101

$115 total

includes taxes & fees

Oct 13 - Oct 14

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

10. DoubleTree by Hilton Hotel Annapolis

Annapolis

$97

$110 total

includes taxes & fees

Oct 12 - Oct 13

11. Village Inn Annapolis MD

Annapolis

$83

$95 total

includes taxes & fees

Oct 5 - Oct 6

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

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

12. St Michaels Inn

St. Michaels

$99

$109 total

includes taxes & fees

Oct 5 - Oct 6

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

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

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

13. Hilton Garden Inn Annapolis Downtown

Annapolis

$114

$130 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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.

14. Graduate by Hilton Annapolis

Annapolis

$147

$167 total

includes taxes & fees

Oct 26 - Oct 27

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

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

15. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

$110

$125 total

includes taxes & fees

Oct 25 - Oct 26

A two-story house with a covered porch, a staircase, and a garden area.

A row of stationary bicycles with green frames and white seats, parked outdoors.

A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

16. Haven Point Inn and Gallery

Rock Hall

$134

$148 total

includes taxes & fees

Oct 7 - Oct 8

A boat deck with a white bench and a view of a calm lake and distant trees.

A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

A buffet with various food items including fruits, pastries, and salads.

17. Inn at Huntingfield Creek

Rock Hall

$178

$198 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

18. Best Western Annapolis

Annapolis

$80

$91 total

includes taxes & fees

Oct 12 - Oct 13

A modern lobby with a reception desk, seating area, and potted plants.

A Hilton Garden Inn with a large building and a smaller entrance building.

A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

A modern bar area with a wooden counter, bar stools, and a wine display.

19. Hilton Garden Inn Annapolis

Annapolis

$101

$115 total

includes taxes & fees

Oct 25 - Oct 26

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

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

$129

$142 total

includes taxes & fees

Oct 5 - Oct 6

View all properties

Go beyond your typical stay in Chester

Top landmarks in Chester

Chesapeake Exploration Center

Chesapeake Exploration Center is worth a visit, located 0.8 mi (1.4 km) from central Kent Narrows.

See properties

Learn more about Chester

The region around Chester is home to attractions such as Chesapeake Exploration Center and Northern Chesapeake Bay.

See all hotels in Chester

Check out reviews of Chester hotels guests love

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Exceptional

Joe

Inn at Huntingfield Creek

Rock Hall

10/10 Exceptional

George

A marina with boats docked at wooden piers, surrounded by greenery.

A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

A covered patio area with wicker furniture and a view of a building with large windows.

A building with a sign reading "The Inn."

Knapps Narrows Marina & Inn

Sherwood

10/10 Exceptional

Stan and Joan

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

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

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

Hampton Inn Easton

Easton

10/10 Exceptional

Anonymous traveler

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.

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Exceptional

Julie

Hilton Garden Inn Annapolis

Annapolis

10/10 Exceptional

Judith

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Exceptional

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Exceptional

Chuck

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Exceptional

Kathie

Kent Island Resort

Stevensville

10/10 Exceptional

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Best Western Kent Narrows Inn

Grasonville

10/10 Exceptional

Valerie

Quality Inn Grasonville near Kent Island

Grasonville

10/10 Exceptional

My wife and have been staying here off and on for a few years now. We have always found it to a lovely place stay . The staff there is especially courteous and helpful whenever a special need arises ! We give special notice of thanks to general manager Amy Patel for her attention to service and her pleasant attitude at all times ! Her caring manner and attention to detail are par excellence ! The cleanliness , breakfast included , location and the inground pool make this a sure bet for any...

Chuck

Historic Inns of Annapolis

Historic District

10/10 Exceptional

Robert

A two-story house with a front porch, large windows, and a well-maintained lawn.

A cozy living room with a fireplace, two patterned armchairs, a coffee table with a vase, and a bookshelf.

A house with a covered porch, outdoor seating, and string lights.

A dining area with a fireplace, framed botanical prints, and a vase with flowers.

1313 West Luxury Boutique Hotel

Homewood

10/10 Exceptional

Sheila

Frequently Asked Questions

What accommodations do travelers recommend in Chester?

Guests like Hilton Garden Inn Kent Island Marina, The Inn at Chesapeake Bay Beach Club and Hyatt Place Kent Narrows & Marina.

Can I book a refundable accommodation in Chester?

If you're looking for the flexibility to change your travel plans to Chester, most properties provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Chester if I want a vacation rental instead of a traditional hotel?

If you want to find a good alternative to a hotel, review our selection of 8 vacation homes.

What will the weather in Chester be like during my visit?

July and August are typically the warmest months in Chester when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. July and October are the months with the most rain.

Why should I book my Chester hotel through Hotels.com?

There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.