Chester Holiday Rentals, Maryland: Private House Rentals

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

Two Adirondack chairs facing a calm body of water with a clear sky above.

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.

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

฿3,705

฿4,112 total

includes taxes & fees

25 Oct - 26 Oct

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.

2. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

฿5,101

฿5,662 total

includes taxes & fees

2 Nov - 3 Nov

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 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

฿6,418

฿7,978 total

includes taxes & fees

19 Oct - 20 Oct

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.

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

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

4. Hilton Garden Inn Kent Island Marina

Grasonville

roney

฿4,667

฿5,181 total

includes taxes & fees

19 Oct - 20 Oct

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

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

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

5. Best Western Kent Narrows Inn

Grasonville

Beth

฿3,622

฿4,020 total

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

6. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

฿3,222

฿3,576 total

includes taxes & fees

2 Nov - 3 Nov

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

7. Kent Island Resort

Stevensville

Bethany

฿4,849

฿6,514 total

includes taxes & fees

27 Oct - 28 Oct

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

A marina with multiple boats docked during sunset.

8. Historic Inns of Annapolis

Historic District

Ashley

฿3,055

฿4,630 total

includes taxes & fees

2 Nov - 3 Nov

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

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

฿3,251

฿3,706 total

includes taxes & fees

12 Oct - 13 Oct

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

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.

10. Graduate by Hilton Annapolis

Annapolis

Mark

฿4,944

฿5,636 total

includes taxes & fees

26 Oct - 27 Oct

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 modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

11. The Westin Annapolis

Annapolis

Bobbi

฿6,678

฿7,613 total

includes taxes & fees

25 Oct - 26 Oct

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

12. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

฿3,825

฿4,361 total

includes taxes & fees

2 Nov - 3 Nov

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 lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

13. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

฿3,705

฿4,223 total

includes taxes & fees

11 Oct - 12 Oct

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

A microwave, a coffee maker, and a refrigerator in a kitchen area.

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

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

14. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

฿3,691

฿4,208 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 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".

15. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

฿3,994

฿4,553 total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a table set for two, overlooking a marina with boats.

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

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

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

16. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

฿8,529

฿9,723 total

includes taxes & fees

12 Oct - 13 Oct

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 with a covered entrance, multiple floors, and a parking lot.

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.

17. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

฿4,552

฿5,007 total

includes taxes & fees

11 Oct - 12 Oct

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 room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

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

18. Best Western Plus Easton Inn & Suites

Easton

Lori

฿4,329

฿4,762 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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

A golf course with a water hazard and surrounding trees.

19. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

฿17,216

฿18,937 total

includes taxes & fees

26 Oct - 27 Oct

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.

20. The Wildset

Downtown St. Michaels

Sarah

฿7,713

฿9,326 total

includes taxes & fees

3 Nov - 4 Nov

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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

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."

Best Western Annapolis

8/10 Good

"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."

Sonesta ES Suites Annapolis

10/10 Excellent

"It is an excellent value for the cost!"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

฿2,688

฿3,065 total

12 Oct - 13 Oct

includes taxes & fees

7.8/10 Good! (1,005 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿2,990

฿3,289 total

7 Oct - 8 Oct

includes taxes & fees

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

฿3,402

฿3,878 total

28 Oct - 29 Oct

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,622

฿4,020 total

13 Oct - 14 Oct

includes taxes & fees

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

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,691

฿4,208 total

25 Oct - 26 Oct

includes taxes & fees

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

฿4,329

฿4,762 total

7 Oct - 8 Oct

includes taxes & fees

9.2/10 Wonderful! (1,004 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 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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Find hotels in Chester, MD from ฿3,065

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. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. Historic Inns of Annapolis

9. DoubleTree by Hilton Hotel Annapolis

10. Graduate by Hilton Annapolis

11. The Westin Annapolis

12. Hilton Garden Inn Annapolis Downtown

13. Crowne Plaza Annapolis by IHG

14. Holiday Inn Express & Suites Annapolis by IHG

15. SpringHill Suites by Marriott Annapolis

16. Annapolis Waterfront Hotel, Autograph Collection

17. Fairfield Inn & Suites by Marriott Easton

18. Best Western Plus Easton Inn & Suites

19. Inn at Perry Cabin

20. The Wildset

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

Hilton Garden Inn Annapolis Downtown

Best Western Annapolis

Sonesta ES Suites Annapolis

St Michaels Inn

The Westin Annapolis

More cheap stays in Chester

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Best Western Kent Narrows Inn

Holiday Inn Express & Suites Annapolis by IHG

Best Western Plus Easton Inn & Suites

Frequently asked questions

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