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Hotels in Chestertown

October 2026
12
November 2026

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This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 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.
An aerial view of a coastal town with a marina, houses, and a bridge in the background.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
$89
$136 total
includes taxes & fees
Nov 11 - Nov 12
Historic Inns of Annapolis
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 hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
$98
$108 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
An indoor water park with multiple slides, a water fountain, and seating areas.
An indoor adventure park with rope bridges, climbing structures, and artificial trees.
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.

3. Great Wolf Lodge Perryville

Great Wolf Lodge Perryville
Perryville
$207
$232 total
includes taxes & fees
Oct 13 - Oct 14
Great Wolf Lodge Perryville
A hotel room with a sofa, two beds, a painting, and a lamp.
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.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

4. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
$72
$80 total
includes taxes & fees
Oct 18 - Oct 19
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 campfire in a stone fire pit by a lakeside at sunset.
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.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
$120
$137 total
includes taxes & fees
Oct 14 - Oct 15
The Lodge at Great Oak Landing
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 a wooden cabinet, a television, a sofa, and a dining table.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

6. Driftwood Inn

Driftwood Inn
Chestertown
$64
$70 total
includes taxes & fees
Oct 13 - Oct 14
Driftwood Inn
A modern kitchen with a built-in coffee station, a toaster, and a variety of food items on display.
A gym with exercise equipment, weight racks, and a large mirror.
A modern hotel lobby with a seating area, a reception desk, and a dining area.
A reception area with two reception desks, a cityscape mural, and a clock on the wall.

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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Rossville
$73
$84 total
includes taxes & fees
Oct 18 - Oct 19
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
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 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 bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

8. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
$147
$167 total
includes taxes & fees
Oct 26 - Oct 27
Graduate by Hilton Annapolis
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 modern bar area with a long counter, bar stools, and shelves stocked with various bottles.
A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.

9. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
$106
$121 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Annapolis Downtown
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$152
$169 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Place Kent Narrows & Marina
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 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.

11. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
$85
$96 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn & Suites Edgewood/Aberdeen-South
An indoor swimming pool with clear water, a changing room, and exercise equipment.
A living room with a fireplace, a television mounted above it, and a coffee table with decorative items.
A spacious lobby with a fireplace, comfortable seating, and large windows.
An outdoor patio area with wicker furniture and a small table, surrounded by brick buildings and a well-maintained garden.

12. Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh
Nottingham
$102
$117 total
includes taxes & fees
Oct 18 - Oct 19
Hilton Garden Inn Baltimore/White Marsh
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 hotel room with a desk, chair, television, and a painting on the wall.
A hotel dining area with a long wooden table, multiple chairs, and a buffet counter.

13. Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh
Nottingham
$102
$117 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn Baltimore/White Marsh
A modern living room with a fireplace, a large painting of a sunset over a bridge, and a cozy seating area.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

14. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
$204
$252 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club
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 hotel lobby with a reception desk, seating area, and a large screen.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.

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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
$79
$88 total
includes taxes & fees
Nov 2 - Nov 3
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
$105
$117 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Annapolis East-Kent Island by IHG
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.

17. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
$223
$254 total
includes taxes & fees
Oct 26 - Oct 27
Annapolis Waterfront Hotel, Autograph Collection
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 dining area with tables and chairs, a television mounted on the wall, and a patterned carpet.

18. Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh
Nottingham
$110
$127 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott White Marsh
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 spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.

19. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
$139
$154 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Garden Inn Kent Island Marina
A boat deck with a white bench and a view of a calm lake and distant trees.
A sunflower field with a white barn and a large house in the background.
A buffet with various food items including fruits, pastries, and salads.
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.

20. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
$178
$198 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek
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Go beyond your typical stay in Chestertown

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Apart­ment
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Our prices for hotels in Chestertown are cheapest in January

Price trends for hotels in Chestertown

Pricing is based on two traveler single night rates
View properties in October

October

High 19°C / low 12°C. Sunny most days.
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Monthly weather averages (˚C)

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

Check out reviews of Chestertown hotels guests love

A boat deck with a white bench and a view of a calm lake and distant trees.
A sunflower field with a white barn and a large house in the background.
A buffet with various food items including fruits, pastries, and salads.
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

10/10 Exceptional

United States
George
Inn at Huntingfield Creek
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 bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
A garden with a lawn and a table with chairs under a canopy.

Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall

10/10 Exceptional

United States
Gary R.
Haven Point Inn and Gallery
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 hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Exceptional

United States
Laura
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 campfire in a stone fire pit by a lakeside at sunset.
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.

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown

10/10 Exceptional

United States
Jamie
The Lodge at Great Oak Landing
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 living room with a fireplace, a chandelier, and a sofa.
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

86 State Circle - Luxury Boutique Hotel
Historic District

10/10 Exceptional

United States
Robert
86 State Circle - Luxury Boutique Hotel
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville

10/10 Exceptional

United States
Joe
Hyatt Place Kent Narrows & Marina
A white two-story building with a central entrance, a staircase, and a small garden area.
A couple standing in front of a black wooden building with white-framed windows.
A table with a champagne bottle and glasses, a lamp, and a window with blinds.
A bookshelf with books, decorative items, and a fireplace.

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
Annapolis

10/10 Exceptional

United States
Reyna
134 Prince - Luxury Boutique Hotel
A modern living room with a fireplace, a large painting of a sunset over a bridge, and a cozy seating area.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville

10/10 Exceptional

United States
Chuck
The Inn at Chesapeake Bay Beach Club
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 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.

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood

10/10 Exceptional

United States
John
Hampton Inn & Suites Edgewood/Aberdeen-South
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 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.

Kent Island Resort

Kent Island Resort
Stevensville

10/10 Exceptional

United States
John
Kent Island Resort
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville

10/10 Exceptional

United States
Christina
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
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.
A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air

10/10 Exceptional

United States
Ami
Hilton Garden Inn Bel Air
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 spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville

10/10 Exceptional

United States
Kathie
Hilton Garden Inn Kent Island Marina
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.
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 modern restaurant with a long counter, multiple seating areas, and pendant lighting.

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown

10/10 Exceptional

United States
Anonymous traveler
Fairfield Inn & Suites by Marriott Middletown
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.
A hotel reception desk with a blue wall featuring the Holiday Inn Express logo, a check-in/out sign, and a 'No Pets' sign.

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

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

10/10 Exceptional

United States
Heather
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A modern building with a covered entrance, stone pillars, and a parking lot with cars.
A reception area with two reception desks, a glass partition, and a wall with geometric patterns.
A hotel room with a coffee machine, a bed, and a window with a view.
A hotel lobby with a sofa, armchairs, a small table, a desk with a computer, and a TV.

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
Middletown

10/10 Exceptional

United States
Christine
Holiday Inn Express & Suites Middletown 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

10/10 Exceptional

United States
Rachael
SpringHill Suites Baltimore White Marsh/Middle River

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.