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

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Our top choices for Chester hotels

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1. Laurel Grove Inn on the South

Laurel Grove Inn on the South
Annapolis
United States
Ruth
￥28,481
￥32,468 total
includes taxes & fees
Aug 23 - Aug 24
Laurel Grove Inn on the South
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

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
￥26,424
￥29,331 total
includes taxes & fees
Sep 8 - Sep 9
Hyatt Place Kent Narrows & Marina
Two Adirondack chairs facing a calm body of water with a clear sky above.
A reception desk with a modern design, a digital display, and a check-in counter.
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 buffet with labeled containers of omelets and other dishes.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Jackie
￥20,188
￥22,409 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Annapolis East-Kent Island by IHG
A swimming pool with a mural, lounge chairs, and a hot tub.
A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.
A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.
A modern interior with a dining area, kitchen, and living space.

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
￥20,135
￥22,350 total
includes taxes & fees
Aug 27 - Aug 28
Best Western Kent Narrows Inn
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.
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
￥23,225
￥25,781 total
includes taxes & fees
Aug 30 - Aug 31
Hilton Garden Inn Kent Island Marina
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 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.

6. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United Kingdom
Jamie
￥34,122
￥41,900 total
includes taxes & fees
Aug 31 - Sep 1
The Inn at Chesapeake Bay Beach Club
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 hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

7. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
￥20,412
￥23,270 total
includes taxes & fees
Aug 30 - Aug 31
SpringHill Suites by Marriott Annapolis
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 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 rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

8. Kent Island Resort

Kent Island Resort
Stevensville
United States
Leigh
￥24,451
￥32,520 total
includes taxes & fees
Sep 10 - Sep 11
Kent Island Resort
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.

9. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Faezeh
￥15,943
￥17,698 total
includes taxes & fees
Sep 10 - Sep 11
Quality Inn Grasonville near Kent Island
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
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.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

10. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
eliana
￥15,440
￥17,602 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis
A two-story building with a covered entrance and an American flag.
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.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

11. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Karen
￥13,455
￥14,801 total
includes taxes & fees
Aug 31 - Sep 1
St Michaels Inn
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.

12. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
United States
Margaret
￥21,994
￥24,193 total
includes taxes & fees
Aug 23 - Aug 24
Best Western Plus Easton Inn & Suites
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.
A hotel with a covered entrance, multiple floors, and a parking lot.

13. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
United States
Stephanie
￥21,385
￥23,524 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites by Marriott Easton
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
A historic brick building with a red roof, multiple windows, and a central staircase.
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.

14. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
￥14,648
￥22,109 total
includes taxes & fees
Aug 27 - Aug 28
Historic Inns of Annapolis
A modern building with large windows, a brick facade, and a well-maintained lawn with flower beds.
A hotel reception area with a wooden counter, a large sailboat painting, and a waffle station.
A lobby with a brick wall, three framed pictures, and a patterned carpet.
A swimming pool with lounge chairs and a covered area, surrounded by a fence and buildings.

15. Quality Inn

Quality Inn
Easton
United States
Karen
￥17,970
￥19,767 total
includes taxes & fees
Aug 23 - Aug 24
Quality Inn
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.

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

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
￥15,063
￥17,172 total
includes taxes & fees
Sep 13 - Sep 14
Country Inn & Suites by Radisson, Annapolis, MD
A modern hotel kitchen with a central island, seating area, and various kitchen appliances.
A hotel room with a large bed, a desk with a laptop, a television, and a door with a curtain.
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.

17. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
￥12,676
￥14,450 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Annapolis
A buffet with labeled food stations including omelets and cheese.
A dock with a stop sign, a flag, and a sign for bikes and walk-on passengers.
A lobby with two green armchairs, a small round table, a flat-screen TV mounted on the wall, and a patterned rug on the floor.
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

18. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
United States
Alicia
￥25,159
￥27,675 total
includes taxes & fees
Aug 26 - Aug 27
Holiday Inn Express Easton by IHG

19. Village Inn Annapolis MD

Village Inn Annapolis MD
Annapolis
United States
Stephen
￥13,133
￥14,972 total
includes taxes & fees
Aug 24 - Aug 25
Village Inn Annapolis MD
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

20. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Phyllis
￥14,557
￥16,596 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Annapolis
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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
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

The Wildset

The Wildset

10/10 Excellent
"Stayed before and will stay again. Love it because of location, staff and food."
Paula 3-night trip
Posted 5 hours ago
The Wildset
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 5 hours ago
Crowne Plaza Annapolis by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Spent one night. Friendly staff. Plenty of space and we had a view of the water."
Stacie 1-night trip
Posted 15 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."
Erich 1-night trip
Posted 16 hours ago
Annapolis Waterfront Hotel, Autograph Collection
St Michaels Inn

St Michaels Inn

8/10 Good
"Property was a bit outdated but hopefully the construction will give it the update it needs."
David 2-night trip
Posted 17 hours ago
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"Reasonable value for the money"
Frank 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Annapolis by IHG
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."
Michael 3-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean and comfortable room, helpful staff and great room service!"
Catherine 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Phyllis 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
￥12,676
￥14,450 total
Aug 30 - Aug 31
includes taxes & fees
7.8/10 Good! (1,008 reviews)
Best Western Annapolis
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
￥13,455
￥14,801 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
St Michaels Inn
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
￥15,570
￥17,750 total
Sep 16 - Sep 17
includes taxes & fees
Hampton Inn & Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
￥15,981
￥18,218 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
￥20,135
￥22,350 total
Aug 27 - Aug 28
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Best Western Kent Narrows Inn
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD
￥20,188
￥22,409 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Holiday Inn Express Annapolis East-Kent Island by IHG

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 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.

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