A coastal forested area with a sandy beach and a calm body of water.

Cheap Hotels in Chestertown

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Cheap Hotels in Chestertown

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

A modern lounge area with seating, a fireplace, and a television.

1. Comfort Inn & Suites Chestertown

Chestertown

$107

$119 total

includes taxes & fees

Oct 13 - Oct 14

A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

A hotel room with a bed, a couch, a painting, and a window with curtains.

A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.

2. Red Roof Inn & Suites Chestertown

Chestertown

$72

$80 total

includes taxes & fees

Sep 29 - Sep 30

A row of motel rooms with stone walls and red doors.

A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

A living room with a wooden cabinet, a television, a sofa, and a dining table.

A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Chestertown

$64

$70 total

includes taxes & fees

Sep 27 - Sep 28

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

A campfire in a stone fire pit by a lakeside at sunset.

4. The Lodge at Great Oak Landing

Chestertown

$120

$137 total

includes taxes & fees

Sep 24 - Sep 25

A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

A gym with treadmills, elliptical machines, and a weight machine.

A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

5. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Bel Air

$91

$102 total

includes taxes & fees

Sep 27 - Sep 28

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

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.

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.

6. Haven Point Inn and Gallery

Rock Hall

$149

$165 total

includes taxes & fees

Sep 29 - Sep 30

A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.

A home gym with an elliptical, a treadmill, and a stationary bike.

A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.

7. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

$88

$99 total

includes taxes & fees

Sep 29 - Sep 30

A modern hotel lobby with a long dining table, several chairs, and a bar area.

A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

8. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

$84

$95 total

includes taxes & fees

Sep 29 - Sep 30

A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

A hotel room with two beds, a bathroom, and a seating area.

A modern lobby with a bar area, seating arrangements, and a television screen.

A hotel with a modern facade, a covered entrance, and a red car parked outside.

9. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

$107

$124 total

includes taxes & fees

Oct 1 - Oct 2

A hotel room with a bed, a desk with a chair, a sofa, and a coffee table. There is a TV on the desk and a window with curtains.

A hotel lobby with a reception desk, seating area, and a large screen.

A spacious lobby with a television, multiple seating options, a coffee station, and a large pillar.

A wedding ceremony in front of a large, classical building with steps leading up to the entrance.

10. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Edgewood

$75

$84 total

includes taxes & fees

Sep 24 - Sep 25

A hotel room with two beds, a desk, a chair, a window with curtains, and a large cityscape photograph on the wall.

A Super 8 hotel with a two-story building, a parking lot, and a grassy area with shrubs.

A breakfast counter with a black-and-white photo of a historic building, a bowl of apples, a container of bread, and a coffee machine.

A bathroom with a bathtub, toilet, sink, and a mirror.

11. Super 8 by Wyndham Havre De Grace Aberdeen Area

Havre De Grace

$56

$63 total

includes taxes & fees

Sep 27 - Sep 28

A hotel room with two beds, each with patterned bedding, a nightstand with a lamp, and a framed picture on the wall.

A hotel room with a bed, a desk with a computer, a lamp, and a picture on the wall.

A hotel room with two beds, a desk with a computer, a lamp, and a framed picture on the wall.

A hotel room with a bed, a television on a wooden dresser, a refrigerator, and a microwave.

12. Motel Edgewood

Edgewood

$54

$60 total

includes taxes & fees

Sep 24 - Sep 25

A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.

A hotel room with a sofa, a bed, a desk, and a lamp.

A vending machine with snacks and a drink dispenser.

13. Quality Inn & Suites Bel Air I-95 Exit 77A

Edgewood

$62

$69 total

includes taxes & fees

Sep 27 - Sep 28

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 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.

14. Quality Inn Grasonville near Kent Island

Grasonville

$100

$111 total

includes taxes & fees

Oct 14 - Oct 15

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

A hotel lobby with a checkered wall, a flat-screen TV, a painting, a patterned carpet, and red upholstered chairs.

A hotel dining area with a kitchen in the background, featuring a bar and seating arrangements.

A rectangular swimming pool with a black edge and metal handrails.

15. Ramada Hotel & Conference Center by Wyndham Edgewood

Edgewood

$84

$94 total

includes taxes & fees

Sep 24 - Sep 25

An indoor swimming pool with clear glass walls, a tiled floor, and a bench near the pool.

A reception desk with a dark wood finish, a small potted plant, and a welcome mat.

A hotel room with a desk, chair, and a bed. There is a window with curtains, a lamp, and a mirror on the wall.

A hotel room with a living area, a desk with a computer, a bed, and a wardrobe.

16. Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Edgewood

$63

$70 total

includes taxes & fees

Sep 29 - Sep 30

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 modern food court with a central island, various food stations, and a yogurt display.

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

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

Grasonville

$114

$127 total

includes taxes & fees

Oct 18 - Oct 19

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

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

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

18. Best Western Kent Narrows Inn

Grasonville

$116

$129 total

includes taxes & fees

Sep 29 - Sep 30

A spacious interior with a staircase, a chandelier, a stone wall, and a Day's Inn snack bar.

A hotel room with two beds, wooden headboards, white bedding, and two wall-mounted lamps.

A rectangular pool with a tiled edge, surrounded by a white fence and a yellow umbrella.

A modern building with a large arched entrance, a sign for a restaurant, and a parking lot in front.

19. Days Inn by Wyndham Aberdeen

Aberdeen

$66

$73 total

includes taxes & fees

Sep 27 - Sep 28

A hotel entrance with a clear sign reading "LA QUINTA".

A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.

A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.

A hotel lobby with seating areas, a TV on the wall, and patterned curtains.

20. La Quinta Inn & Suites by Wyndham Aberdeen-APG

Aberdeen

$98

$109 total

includes taxes & fees

Oct 4 - Oct 5

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Top landmarks in Chestertown

Washington College

8.6/10 (87 reviews)

If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.

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River Arts Chestertown

7.4/10 (6 reviews)

If you'd like to get a taste of Chestertown student life, check out River Arts Chestertown, located 0.7 mi (1.1 km) from central Chestertown.

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Chestertown Historic District

If you're planning a bit of sightseeing during your trip, head to Chestertown Historic District— just one of the landmarks located 0.8 mi (1.2 km) from central Chestertown.

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Historical Society of Kent County Maryland

7.4/10 (6 reviews)

Historical Society of Kent County Maryland is 0.7 mi (1.2 km) from central Chestertown, why not stop by during your stay. If you want to experience more of the culture Chestertown has to offer, head to Chestertown Historic District, River Arts Chestertown, and Wilmer Park.

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Rolphs Wharf Marina

8.2/10 (15 reviews)

Imagine strolling along Rolphs Wharf Marina for some great waterfront pics. It's located 3.6 mi (5.8 km) from central Chestertown.

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Wilmer Park

8.2/10 (13 reviews)

Wilmer Park is worth a visit, located 1 mi (1.6 km) from central Chestertown.

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Rolling Road Park

Rolling Road Park is worth a visit, located 0.5 mi (0.9 km) from central Chestertown.

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Kings Town Park

Kings Town Park is worth a visit, located 1.2 mi (1.9 km) from central Chestertown.

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Frequently Asked Questions

Are there any cheap motels in Chestertown?

If you're eager to find a budget-friendly place to stay in Chestertown, consider booking a motel. Take a look at Driftwood Inn where you'll find free WiFi and free parking.

What are the best cheap things to do in Chestertown?

Sightseeing doesn't have to break the bank. For some things to do in Chestertown, try a visit to attractions like Chestertown Historic District and Wilmer Park during your trip. Be certain a visit to Kings Town Park is in your plans.