A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Hotels in Chestertown

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Where to stay in Chestertown?

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.

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

1. Historic Inns of Annapolis

Historic District

$89

$136 total

includes taxes & fees

Nov 11 - Nov 12

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.

A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

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

2. Comfort Inn & Suites Chestertown

Chestertown

$98

$108 total

includes taxes & fees

Nov 8 - Nov 9

An indoor water park with multiple slides, a water fountain, and seating areas.

A restaurant with multiple tables and chairs, a sign reading "Campfire Kitchen", and a large tree in the center.

A spacious lobby with a large stone fireplace, modern seating, and large windows with forest views.

An indoor play area with climbing structures, artificial trees, and a sign reading "Howlin' One."

3. Great Wolf Lodge Perryville

Perryville

$207

$232 total

includes taxes & fees

Oct 13 - Oct 14

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 living room with a fireplace, a television, and a stone accent wall.

4. Red Roof Inn & Suites Chestertown

Chestertown

$72

$80 total

includes taxes & fees

Oct 18 - Oct 19

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 large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

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

5. The Lodge at Great Oak Landing

Chestertown

$120

$137 total

includes taxes & fees

Oct 14 - Oct 15

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

A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

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

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

6. Driftwood Inn

Chestertown

$64

$70 total

includes taxes & fees

Oct 13 - Oct 14

A modern kitchen with a built-in coffee station, a toaster, and a variety of food items on display.

A reception area with two reception desks, a cityscape mural, and a clock on the wall.

A modern hotel lobby with a seating area, a reception desk, and a dining area.

A gym with exercise equipment, weight racks, and a large mirror.

7. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Rossville

$73

$84 total

includes taxes & fees

Oct 18 - Oct 19

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 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.

8. Graduate by Hilton Annapolis

Annapolis

$147

$167 total

includes taxes & fees

Oct 26 - Oct 27

A modern lobby with a seating area, a fireplace, and a bookshelf.

A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.

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

9. Hilton Garden Inn Annapolis Downtown

Annapolis

$106

$121 total

includes taxes & fees

Oct 25 - Oct 26

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

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

An outdoor event area with round tables and a view of the water.

10. Hyatt Place Kent Narrows & Marina

Grasonville

$152

$169 total

includes taxes & fees

Oct 18 - Oct 19

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

A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

11. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

$85

$96 total

includes taxes & fees

Nov 2 - Nov 3

An indoor swimming pool with clear water, a changing room, and exercise equipment.

A spacious lobby with a fireplace, comfortable seating, and large windows.

A living room with a fireplace, a television mounted above it, and a coffee table with decorative items.

A hotel entrance with a covered walkway, brick facade, and multiple windows.

12. Hilton Garden Inn Baltimore/White Marsh

Nottingham

$102

$117 total

includes taxes & fees

Oct 18 - Oct 19

A Hampton Inn with a 'Welcome' sign under a covered entrance, surrounded by greenery.

A hotel room with a wooden cabinet, a sink, a mirror, a chair, and a table.

A patio area with a fire pit, outdoor seating, and umbrellas providing shade.

A hotel room with a desk, chair, television, and a painting on the wall.

13. Hampton Inn Baltimore/White Marsh

Nottingham

$102

$117 total

includes taxes & fees

Oct 18 - Oct 19

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

14. The Inn at Chesapeake Bay Beach Club

Stevensville

$204

$252 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

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

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

Edgewood

$79

$88 total

includes taxes & fees

Nov 2 - Nov 3

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 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.

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

Grasonville

$105

$117 total

includes taxes & fees

Nov 8 - Nov 9

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

A waterfront area with boats docked, a clear sky, and buildings in the background.

17. Annapolis Waterfront Hotel, Autograph Collection

Historic District

$223

$254 total

includes taxes & fees

Oct 26 - Oct 27

A lobby with a reception desk, seating area, and a fireplace.

A kitchenette with a microwave, refrigerator, and shelves stocked with snacks and beverages.

A hotel room with a seating area featuring green and purple chairs, a small white table, and a lamp. A framed artwork is on the wall, and there is a window with curtains.

A hotel room with a large bed, a wooden headboard, a desk with a chair, and a patterned carpet.

18. Fairfield Inn & Suites by Marriott White Marsh

Nottingham

$110

$127 total

includes taxes & fees

Oct 18 - Oct 19

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

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

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

19. Hilton Garden Inn Kent Island Marina

Grasonville

$139

$154 total

includes taxes & fees

Oct 19 - Oct 20

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 buffet with various food items including fruits, pastries, and salads.

A sunflower field with a white barn and a large house in the background.

20. Inn at Huntingfield Creek

Rock Hall

$178

$198 total

includes taxes & fees

Nov 1 - Nov 2

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Go beyond your typical stay in Chestertown

Our prices for hotels in Chestertown are cheapest in January

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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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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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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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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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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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)

Why not give yourself a treat with a trip to Garfield Center for the Arts at the Prince Theater, one of the family attractions located 0.7 mi (1.2 km) from central Chestertown. If you have fun at Garfield Center for the Arts at the Prince Theater, you'll love Schooner Sultana, just a short walk away.

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Crumpton Auction

8.8/10 (3 reviews)

Why not give yourself a treat with a trip to Crumpton Auction, one of the family attractions located 8.4 mi (13.5 km) from central Chestertown. If you'd also like to explore some of the parks in Chestertown, Pinkney Park is nearby.

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Sumner Hall

Sumner Hall is 0.8 mi (1.3 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 Historical Society of Kent County Maryland.

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Learn more about Chestertown

Cobblestone streets wind past Federal-era mansions in this Chesapeake Bay gem where history feels less like a museum and more like a neighbor who won't stop talking. The Chester River waterfront invites sailing adventures aboard traditional skipjacks, while Washington College students add youthful energy to the centuries-old town. High Street's galleries showcase local artists who've captured the distinctive Eastern Shore light. The Garfield Center for the Arts occupies a lovingly restored 1920s theater where performances continue in a space that's seen everything from vaudeville to indie films. Don't miss First Fridays when galleries stay open late and locals debate whether the best crab cakes come from waterfront restaurants or roadside shacks.

See all hotels in Chestertown

Check out reviews of Chestertown hotels guests love

Inn at Huntingfield Creek

Rock Hall

10/10 Exceptional

George

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

A row of stationary bicycles with green frames and white seats, parked outdoors.

A garden with a lawn and a table with chairs under a canopy.

A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

Haven Point Inn and Gallery

Rock Hall

10/10 Exceptional

Gary R.

Comfort Inn & Suites Chestertown

Chestertown

10/10 Exceptional

Laura

The Lodge at Great Oak Landing

Chestertown

10/10 Exceptional

Jamie

A cozy bar area with a brick archway, wooden cabinets, and a dining table with chairs.

A church with a spire, surrounded by trees and illuminated by warm lights.

A bedroom with a large window, a chair, a bedside table with a lamp, and a bookshelf.

A cozy lounge area with a cushioned bench, two small tables with lamps, a brick wall, and a fireplace.

86 State Circle - Luxury Boutique Hotel

Historic District

10/10 Exceptional

Robert

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Exceptional

Joe

A white two-story building with a central entrance, a staircase, and a small garden area.

A bookshelf with books, decorative items, and a fireplace.

A table with a champagne bottle and glasses, a lamp, and a window with blinds.

A couple standing in front of a black wooden building with white-framed windows.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Exceptional

Reyna

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Exceptional

Chuck

Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

10/10 Exceptional

John

A large, two-story barn-style building with a covered front porch and a garage.

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.

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.

Kent Island Resort

Stevensville

10/10 Exceptional

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Exceptional

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

A modern building with a stone facade, large windows, and outdoor seating area with chairs.

Hilton Garden Inn Bel Air

Bel Air

10/10 Exceptional

Ami

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Exceptional

Kathie

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 Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.

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.

Fairfield Inn & Suites by Marriott Middletown

Middletown

10/10 Exceptional

Anonymous traveler

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

An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

10/10 Exceptional

Heather

A modern building with a covered entrance, stone pillars, and a parking lot with cars.

A hotel lobby with a sofa, armchairs, a small table, a desk with a computer, and a TV.

A hotel room with a coffee machine, a bed, and a window with a view.

A modern restaurant with booths and tables, a TV screen displaying AT&T, and a wooden ceiling.

Holiday Inn Express & Suites Middletown by IHG

Middletown

10/10 Exceptional

Christine

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

An outdoor patio with brick walls, green chairs, and a fire pit.

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

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

SpringHill Suites Baltimore White Marsh/Middle River

Middle River

10/10 Exceptional

Rachael

Frequently Asked Questions

What hotels do travelers recommend in Chestertown?

Guests like Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing and Comfort Inn & Suites Chestertown.

Can I book a refundable hotel in Chestertown?

If you're looking for the flexibility to change your plans to Chestertown, most properties offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Chestertown if I want a vacation home instead of a hotel?

If you want to find a good alternative to a hotel, review our selection of 29 vacation homes. You can also consider one of the 5 apartments or 5 cottages.

What will the weather in Chestertown be like during my trip?

July and August are typically the warmest months in Chestertown when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. August and July are the months with the most rain.

Why should I book my Chestertown hotel with Hotels.com?

There are lots of reasons to book your Chestertown trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Hotels in Chestertown

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Chestertown?

1. Historic Inns of Annapolis

2. Comfort Inn & Suites Chestertown

3. Great Wolf Lodge Perryville

4. Red Roof Inn & Suites Chestertown

5. The Lodge at Great Oak Landing

6. Driftwood Inn

7. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

8. Graduate by Hilton Annapolis

9. Hilton Garden Inn Annapolis Downtown

10. Hyatt Place Kent Narrows & Marina

11. Hampton Inn & Suites Edgewood/Aberdeen-South

12. Hilton Garden Inn Baltimore/White Marsh

13. Hampton Inn Baltimore/White Marsh

14. The Inn at Chesapeake Bay Beach Club

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

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

17. Annapolis Waterfront Hotel, Autograph Collection

18. Fairfield Inn & Suites by Marriott White Marsh

19. Hilton Garden Inn Kent Island Marina

20. Inn at Huntingfield Creek

Go beyond your typical stay in Chestertown

Price trends for hotels in Chestertown

October

Top landmarks in Chestertown

Washington College

Chestertown Historic District

Rolphs Wharf Marina

River Arts Chestertown

Historical Society of Kent County Maryland

Garfield Center for the Arts at the Prince Theater

Crumpton Auction

Sumner Hall

Learn more about Chestertown

Check out reviews of Chestertown hotels guests love

Inn at Huntingfield Creek

10/10 Exceptional

Haven Point Inn and Gallery

10/10 Exceptional

Comfort Inn & Suites Chestertown

10/10 Exceptional

The Lodge at Great Oak Landing

10/10 Exceptional

86 State Circle - Luxury Boutique Hotel

10/10 Exceptional

Hyatt Place Kent Narrows & Marina

10/10 Exceptional

134 Prince - Luxury Boutique Hotel

10/10 Exceptional

The Inn at Chesapeake Bay Beach Club

10/10 Exceptional

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Exceptional

Kent Island Resort

10/10 Exceptional

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Exceptional

Hilton Garden Inn Bel Air

10/10 Exceptional

Hilton Garden Inn Kent Island Marina

10/10 Exceptional

Fairfield Inn & Suites by Marriott Middletown

10/10 Exceptional

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

10/10 Exceptional

Holiday Inn Express & Suites Middletown by IHG

10/10 Exceptional

SpringHill Suites Baltimore White Marsh/Middle River

10/10 Exceptional

Frequently Asked Questions

What hotels do travelers recommend in Chestertown?

Can I book a refundable hotel in Chestertown?

Where can I stay in Chestertown if I want a vacation home instead of a hotel?

What will the weather in Chestertown be like during my trip?

Why should I book my Chestertown hotel with Hotels.com?