Hotels in Chester

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Where to stay in Chester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Chester on Hotels.com. These Chester hotels consistently deliver on quality, location and traveler experience. Last updated on October 13, 2026.

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

An outdoor event area with round tables and a view of the water.

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.

1. Hyatt Place Kent Narrows & Marina

Grasonville

CNY1,017

CNY1,129 total

includes taxes & fees

Oct 25 - Oct 26

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

CNY736

CNY817 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 spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

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

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

CNY1,366

CNY1,686 total

includes taxes & fees

Nov 2 - Nov 3

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

4. Hilton Garden Inn Kent Island Marina

Grasonville

CNY928

CNY1,030 total

includes taxes & fees

Oct 19 - Oct 20

A hotel room with two beds, a desk, a chair, and a bathroom.

A poolside area with lounge chairs and a mural of a sunset over water.

A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.

5. Best Western Kent Narrows Inn

Grasonville

CNY602

CNY668 total

includes taxes & fees

Nov 8 - Nov 9

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 Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

6. Quality Inn Grasonville near Kent Island

Grasonville

CNY605

CNY671 total

includes taxes & fees

Nov 8 - Nov 9

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

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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.

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

7. Kent Island Resort

Stevensville

CNY810

CNY1,120 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.

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.

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

8. Historic Inns of Annapolis

Historic District

CNY573

CNY883 total

includes taxes & fees

Oct 20 - Oct 21

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 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

CNY708

CNY807 total

includes taxes & fees

Oct 18 - Oct 19

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

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

10. Annapolis Waterfront Hotel, Autograph Collection

Historic District

CNY1,494

CNY1,703 total

includes taxes & fees

Nov 1 - Nov 2

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".

11. SpringHill Suites by Marriott Annapolis

Annapolis

CNY797

CNY908 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

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

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

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

CNY703

CNY801 total

includes taxes & fees

Oct 25 - Oct 26

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.

13. The Westin Annapolis

Annapolis

CNY1,332

CNY1,518 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 buffet with various food items, including omelets and baked goods, in stainless steel containers.

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.

14. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

CNY676

CNY771 total

includes taxes & fees

Oct 18 - Oct 19

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

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.

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

15. Inn at Perry Cabin

Downtown St. Michaels

CNY3,433

CNY3,777 total

includes taxes & fees

Nov 8 - Nov 9

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 restaurant with a yellow cushioned bench, wooden tables, and chairs.

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

16. Hilton Garden Inn Annapolis Downtown

Annapolis

CNY708

CNY807 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.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

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

17. Fairfield Inn & Suites by Marriott Easton

Easton

CNY905

CNY995 total

includes taxes & fees

Oct 18 - Oct 19

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

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

18. The Wildset

Downtown St. Michaels

CNY1,533

CNY1,853 total

includes taxes & fees

Nov 4 - Nov 5

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

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

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

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

19. Best Western Plus Easton Inn & Suites

Easton

CNY863

CNY950 total

includes taxes & fees

Oct 18 - Oct 19

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 hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

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

20. Graduate by Hilton Annapolis

Annapolis

CNY982

CNY1,120 total

includes taxes & fees

Oct 26 - Oct 27

View all properties

Go beyond your typical stay in Chester

Pet friendly

Pool

Spa

Family friendly

Hot tub

Cottage

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

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

Check out reviews of Chester hotels guests love

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"We stay here frequently. The best hotel in a great location."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Sonesta ES Suites Annapolis

10/10 Excellent

"Shalinda was the most welcoming front desk staff i have ever encountered."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Good stay , wish the hot tub worked"

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Breakfast need to work on, it has nothing to eat then we have to go out buy breakfast. Everythingelse is good."

Baymont by Wyndham Easton

10/10 Excellent

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"

The Westin Annapolis

10/10 Excellent

"Easy parking. Super comfy bed."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"no"

Frequently asked questions

How much does a hotel room cost in Chester?

You can find top hotels in Chester from CNY590 with options to suit your budget and needs. If you're after an affordable hotel in Chester that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Chester hotels?

Discover great deals on Chester hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Chester hotels.

Can I book Chester hotels with free cancellation?

It's easy to book a refundable Chester hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Chester?

If you're looking for hotels in central Chester, check out Hyatt Place Kent Narrows & Marina and Hilton Garden Inn Kent Island Marina. Travelers love Hyatt Place Kent Narrows & Marina for its location, as well as the indoor pool, restaurant and bar/lounge this hotel offers. Hilton Garden Inn Kent Island Marina is another popular central hotel with an indoor pool, a hot tub and a restaurant.

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.

Keep exploring

Book Hotels in Chester on Hotels.com