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Oct 8 - Oct 9
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Oct 9 - Oct 10
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Oct 9 - Oct 11
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Oct 16 - Oct 18

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Our top choices for Chestertown hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
₩131,266
₩145,705 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
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 large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Sandra
₩144,558
₩165,273 total
includes taxes & fees
Oct 20 - Oct 21
The Lodge at Great Oak Landing
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A multi-story brick building with a covered entrance and a parking lot.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
₩96,360
₩106,959 total
includes taxes & fees
Oct 20 - Oct 21
Red Roof Inn & Suites Chestertown
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 hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A two-story building with a brick facade, large windows, and a sloped roof.

4. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
₩84,995
₩94,351 total
includes taxes & fees
Oct 12 - Oct 13
Driftwood Inn
A two-story house with a covered porch, a staircase, and a garden area.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
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.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall
United States
Joe
₩178,890
₩198,568 total
includes taxes & fees
Oct 14 - Oct 15
Haven Point Inn and Gallery
A boat deck with a white bench and a view of a calm lake and distant trees.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.
A sunflower field with a white barn and a large house in the background.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

6. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
United States
Christine
₩214,762
₩238,386 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek
Two Adirondack chairs facing a calm body of water with a clear sky above.
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 reception desk with a modern design, a digital display, and a check-in counter.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
₩132,660
₩147,253 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
₩203,452
₩225,831 total
includes taxes & fees
Oct 20 - Oct 21
Hyatt Place Kent Narrows & Marina
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A hotel with a modern facade, a covered entrance, and a red car parked outside.
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.

9. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Juanita
₩143,353
₩165,573 total
includes taxes & fees
Oct 15 - Oct 16
SpringHill Suites Baltimore White Marsh/Middle River
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
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.

10. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
₩256,275
₩318,555 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
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.

11. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
₩185,489
₩205,892 total
includes taxes & fees
Oct 20 - Oct 21
Hilton Garden Inn Kent Island Marina
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.
A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.

12. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
United States
Sharon
₩135,541
₩150,450 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Middletown
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 dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A gym with treadmills, elliptical machines, and a weight machine.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
United States
Vanessa
₩119,394
₩133,720 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

14. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Lyn
₩114,275
₩127,987 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Edgewood/Aberdeen-South
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 spacious lobby with a staircase, a reception desk, and a dining area.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Crystal
₩121,029
₩134,342 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Grasonville near Kent Island
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.

16. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
United States
Jaccilynne
₩146,931
₩164,563 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Bel Air
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.
A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.
A home gym with an elliptical, a treadmill, and a stationary bike.
A hotel reception desk with a blue wall featuring the Holiday Inn Express logo, a check-in/out sign, and a 'No Pets' sign.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
United States
Wanee
₩111,220
₩124,566 total
includes taxes & fees
Nov 5 - Nov 6
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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 vending area with two beverage dispensers, a wall-mounted display of personal care items, and shelves stocked with snacks and beverages.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
United States
robin
₩135,541
₩151,807 total
includes taxes & fees
Oct 15 - Oct 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A traditional house with a covered porch, white picket fence, and lush greenery.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.

19. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
₩234,232
₩262,340 total
includes taxes & fees
Oct 12 - Oct 13
Vandiver Inn
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.
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.

20. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Beth
₩120,439
₩133,688 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
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Hotels recommended for families in Chestertown

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
₩131,266
₩145,705 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A multi-story brick building with a covered entrance and a parking lot.

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
₩96,360
₩106,959 total
includes taxes & fees
Oct 20 - Oct 21
Red Roof Inn & Suites Chestertown
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 large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
₩144,558
₩165,273 total
includes taxes & fees
Oct 20 - Oct 21
The Lodge at Great Oak Landing
A boat deck with a white bench and a view of a calm lake and distant trees.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.
A sunflower field with a white barn and a large house in the background.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
₩214,762
₩238,386 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek
Two Adirondack chairs facing a calm body of water with a clear sky above.
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 reception desk with a modern design, a digital display, and a check-in counter.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
₩132,660
₩147,253 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A hotel with a modern facade, a covered entrance, and a red car parked outside.
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.

SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
₩143,353
₩165,573 total
includes taxes & fees
Oct 15 - Oct 16
SpringHill Suites Baltimore White Marsh/Middle River
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.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
₩203,452
₩225,831 total
includes taxes & fees
Oct 20 - Oct 21
Hyatt Place Kent Narrows & Marina
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 dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A gym with treadmills, elliptical machines, and a weight machine.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
₩119,394
₩133,720 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
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River Arts Chestertown

7.4/10 (6 reviews)
Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
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Chestertown Historic District

This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick sidewalks along the Chester River or visit during the annual Tea Party Festival reenactments.
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Historical Society of Kent County Maryland

7.4/10 (6 reviews)
Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
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Wilmer Park

8.2/10 (13 reviews)
Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.
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Kings Town Park

Kings Town Park offers serene pathways winding through lush greenery in Chestertown, Maryland. Enjoy morning strolls or invigorating runs along the scenic trails away from urban bustle.
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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
This historic 1928 theater offers an intimate setting for plays, music, and lectures in downtown Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening.
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Crumpton Auction

8.8/10 (3 reviews)
Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins.
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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews