𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester (2026)

A coastal town with a marina, a bridge, and a highway.

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Our top choices for Chester hotels

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

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

Grasonville

Marc

₹9,971

₹11,067 total

includes taxes & fees

8 Nov - 9 Nov

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 modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

2. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

₹14,429

₹16,016 total

includes taxes & fees

28 Oct - 29 Oct

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.

3. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

₹20,298

₹24,946 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

An indoor swimming pool with clear views of boats and water.

4. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

₹11,913

₹13,224 total

includes taxes & fees

18 Nov - 19 Nov

A kitchenette with a coffee machine, a framed picture, and a potted plant.

A lobby with a reception desk, a clock, and a wall-mounted deer head.

5. Best Western Kent Narrows Inn

Grasonville

Wesley

₹8,532

₹9,471 total

includes taxes & fees

17 Nov - 18 Nov

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 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.

6. Kent Island Resort

Stevensville

Bethany

₹11,615

₹16,031 total

includes taxes & fees

17 Nov - 18 Nov

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

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.

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

7. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

₹7,923

₹8,795 total

includes taxes & fees

15 Nov - 16 Nov

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

A marina with multiple boats docked during sunset.

8. Historic Inns of Annapolis

Historic District

Jennifer

₹7,971

₹12,333 total

includes taxes & fees

19 Nov - 20 Nov

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

9. The Westin Annapolis

Annapolis

Bobbi

₹18,897

₹21,542 total

includes taxes & fees

25 Oct - 26 Oct

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

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

10. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

₹10,820

₹12,334 total

includes taxes & fees

27 Oct - 28 Oct

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.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

11. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

₹21,195

₹24,162 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a desk with a television, a chair, and a balcony with a view of the city.

A multi-story hotel with a modern design, featuring a prominent entrance with arches and a sign for Hilton Garden Inn.

A conference room with multiple round tables and chairs, large windows with curtains, and a patterned carpet.

A room with a grey armchair, a round wooden side table, a floor lamp, and a window with sheer curtains.

12. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

₹9,975

₹11,372 total

includes taxes & fees

1 Nov - 2 Nov

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.

13. Graduate by Hilton Annapolis

Annapolis

Nadine

₹13,938

₹15,889 total

includes taxes & fees

26 Oct - 27 Oct

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.

14. Crowne Plaza Annapolis by IHG

Annapolis

Jose

₹9,971

₹11,366 total

includes taxes & fees

16 Nov - 17 Nov

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 coffee station with two coffee machines and a variety of coffee pods and cups.

15. Holiday Inn Express Easton by IHG

Easton

Alison

₹14,149

₹15,564 total

includes taxes & fees

25 Oct - 26 Oct

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 reception area with a reception desk, a television, and seating area.

16. SpringHill Suites by Marriott Annapolis

Annapolis

Kaiya

₹11,300

₹12,882 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

17. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

₹12,834

₹14,117 total

includes taxes & fees

25 Oct - 26 Oct

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

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

A golf course with a water hazard and surrounding trees.

18. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

₹46,613

₹51,274 total

includes taxes & fees

18 Nov - 19 Nov

A two-story house with a porch, a front door, and a small garden area.

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

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

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.

19. The Wildset

Downtown St. Michaels

Sarah

₹21,745

₹26,294 total

includes taxes & fees

3 Nov - 4 Nov

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

A sailboat docked at a waterfront with buildings in the background.

A dark blue bookshelf with decorative items and books.

A neatly made bed with white bedding, a striped pillow, and a vase with white flowers on a bedside table.

20. Flag House Inn

Historic District

Nathan

₹22,167

₹25,271 total

includes taxes & fees

26 Oct - 27 Oct

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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening in 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

St Michaels Inn

10/10 Excellent

"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."

Best Western Annapolis

10/10 Excellent

"Super nice staff, Clean rooms, comfortable bed, good breakfast and close to restaurants and less than 5miles to City Dock. I was in Annapolis for work for 5 days, I recommend this hotel, thank you!"

Sonesta ES Suites Annapolis

8/10 Good

"My husband and I were traveling with our 14 month-old son. The room was a good size and had two separate bedrooms, which worked out really well for us. There was a strong odor when we first arrived to our room. We travel with an air purifier for our son, as he sometimes has sinus issues, so that helped. The room itself was a bit dated, although well laid out. The fridge, microwave and dishwasher were all really nice to have. We didn’t get to use the fireplace, as we purchased a log, but we didn’t have a lighter or matches and the property didn’t either. The breakfast every morning was great! Fresh food snd fresh ingredients. Kitchen staff was incredibly friendly and good with our son, too. I’d say 7.5/10, but if they were to update the room and eliminate the odor, I feel like it’d be a 9/10."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Wonderful staff! Had a problem getting into the bed because it was too high and I was too short. They were wonderful with accommodating my needs! They moved me to a new room and location!"

Historic Inns of Annapolis

10/10 Excellent

"Room was great tv reception was not."

Candlewood Suites Annapolis by IHG

10/10 Excellent

"Staff was great and the room was clean!!"

The Tidewater Inn

8/10 Good

"This hotel is a gorgeous historic hotel. It has all character and beauty that you expect in Easton, Maryland. People should be aware that the air conditioning/heat is controlled by the staff. So if it’s hot in the room, you can’t adjust the air conditioning."

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Perfect place to stay! Classy. Clean comfortable amazing staff"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

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

More cheap stays in Chester

St Michaels Inn

1228 S Talbot Street St. Michaels MD

₹7,147

₹7,862 total

19 Nov - 20 Nov

includes taxes & fees

8/10 Very good! (1,007 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

₹7,176

₹8,181 total

17 Nov - 18 Nov

includes taxes & fees

7.8/10 Good! (1,006 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

₹8,532

₹9,471 total

17 Nov - 18 Nov

includes taxes & fees

8/10 Very good! (1,004 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

₹9,021

₹10,284 total

16 Nov - 17 Nov

includes taxes & fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

₹9,263

₹10,560 total

17 Nov - 18 Nov

includes taxes & fees

8.2/10 Very good! (1,007 reviews)

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

₹11,296

₹12,426 total

17 Nov - 18 Nov

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 traveller data. Two other options for your stay in 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 bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What are some accommodation options 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 that offer an on-site 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 accommodation options 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 Eastern Neck National Wildlife Refuge. You'll also find Sandy Point Beach and Queenstown Harbor Golf in the area. Take a look at what more there is 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.

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Book Hotels in Chester on Expedia.com

Chester Hotels from ₹7,862

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. Holiday Inn Express Annapolis East-Kent Island by IHG

2. Hyatt Place Kent Narrows & Marina

3. The Inn at Chesapeake Bay Beach Club

4. Hilton Garden Inn Kent Island Marina

5. Best Western Kent Narrows Inn

6. Kent Island Resort

7. Quality Inn Grasonville near Kent Island

8. Historic Inns of Annapolis

9. The Westin Annapolis

10. DoubleTree by Hilton Hotel Annapolis

11. Annapolis Waterfront Hotel, Autograph Collection

12. Hilton Garden Inn Annapolis Downtown

13. Graduate by Hilton Annapolis

14. Crowne Plaza Annapolis by IHG

15. Holiday Inn Express Easton by IHG

16. SpringHill Suites by Marriott Annapolis

17. Fairfield Inn & Suites by Marriott Easton

18. Inn at Perry Cabin

19. The Wildset

20. Flag House Inn

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

St Michaels Inn

Best Western Annapolis

Sonesta ES Suites Annapolis

The Inn at Chesapeake Bay Beach Club

Historic Inns of Annapolis

Candlewood Suites Annapolis by IHG

The Tidewater Inn

Annapolis Waterfront Hotel, Autograph Collection

Hyatt Place Kent Narrows & Marina

More cheap stays in Chester

St Michaels Inn

Best Western Annapolis

Best Western Kent Narrows Inn

Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Best Western Plus Easton Inn & Suites

Frequently asked questions

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