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Hotels in Chestertown

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Check prices for these dates

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Where to stay in Chestertown?

Free daily full breakfast
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (864)
The price is $102
$113 total
includes taxes & fees
Feb 1 - Feb 2
Comfort Inn & Suites Chestertown
Lobby lounge
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (426)
The price is $72
$80 total
includes taxes & fees
Jan 15 - Jan 16
Red Roof Inn & Suites Chestertown
Lake
Inn at Huntingfield Creek
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59)
The price is $156
$173 total
includes taxes & fees
Jan 11 - Jan 12
Inn at Huntingfield Creek
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (865)
The price is $84
$93 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (947)
The price is $95
$105 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Basic Double or Twin Room | Desk, free WiFi, bed sheets
Motel Edgewood
Motel Edgewood
Motel Edgewood
2.0 star property
Edgewood
7.4 out of 10, Good, (10)
The price is $49
$55 total
includes taxes & fees
Feb 1 - Feb 2
Motel Edgewood
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1000)
The price is $83
$93 total
includes taxes & fees
Jan 14 - Jan 15
Best Western Kent Narrows Inn
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (341)
The price is $89
$100 total
includes taxes & fees
Jan 30 - Jan 31
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (695)
The price is $116
$129 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
The price is $122
$136 total
includes taxes & fees
Jan 12 - Jan 13
Hilton Garden Inn Kent Island Marina
Reception
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1001)
The price is $81
$91 total
includes taxes & fees
Jan 13 - Jan 14
Hampton Inn & Suites Edgewood/Aberdeen-South
View from property
TownePlace Suites by Marriott Edgewood Aberdeen
TownePlace Suites by Marriott Edgewood Aberdeen
TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (101)
The price is $119
$133 total
includes taxes & fees
Jan 11 - Jan 12
TownePlace Suites by Marriott Edgewood Aberdeen
Lobby
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1006)
The price is $79
$89 total
includes taxes & fees
Jan 28 - Jan 29
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Studio Suite, 1 King Bed with Sofa bed, Non Smoking | Free WiFi, bed sheets
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very Good, (1001)
The price is $67
$75 total
includes taxes & fees
Jan 11 - Jan 12
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Bar (on property)
Hilton Garden Inn Bel Air
Hilton Garden Inn Bel Air
Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (237)
The price is $98
$109 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Bel Air
Exterior
Holiday Inn Belcamp - Aberdeen Area by IHG
Holiday Inn Belcamp - Aberdeen Area by IHG
Holiday Inn Belcamp - Aberdeen Area by IHG
3.0 star property
Belcamp
8.4 out of 10, Very Good, (745)
The price is $71
$80 total
includes taxes & fees
Jan 11 - Jan 12
Holiday Inn Belcamp - Aberdeen Area by IHG
Free daily continental breakfast
Quality Inn & Suites Bel Air I-95 Exit 77A
Quality Inn & Suites Bel Air I-95 Exit 77A
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1021)
The price is $52
$58 total
includes taxes & fees
Jan 22 - Jan 23
Quality Inn & Suites Bel Air I-95 Exit 77A
Exterior
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (563)
The price is $83
$93 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Indoor pool
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
2.5 star property
Edgewood
7.2 out of 10, Good, (1000)
The price is $55
$62 total
includes taxes & fees
Jan 14 - Jan 15
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG
Candlewood Suites Aberdeen-Bel Air by IHG
Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (477)
The price is $83
$93 total
includes taxes & fees
Jan 10 - Jan 11
Candlewood Suites Aberdeen-Bel Air by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Budget hotels in Chestertown and vicinity

Basic Double or Twin Room | Desk, free WiFi, bed sheets
Motel Edgewood

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.4 out of 10, Good, (10)
The price is $49
$55 total
includes taxes & fees
Feb 1 - Feb 2
Motel Edgewood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all budget hotels

When is the best time to visit Chestertown?

Our prices for hotels in Chestertown are cheapest in February
Price trends for hotels in Chestertown
Pricing is based on two traveler single night rates
View properties in January
Currently viewing crowd sizes and weather for January.
Typical weather for Chestertown
January
High 4°C / low -2°C. Partly sunny.
View properties in January
4°
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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
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6°
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February, no crowd data, average high temperature 6 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
11°
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March, no crowd data, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
17°
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April, no crowd data, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
22°
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May, no crowd data, average high temperature 22 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
26°
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June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
29°
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
22°
28°
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August, no crowd data, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
25°
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September, no crowd data, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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19°
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October, no crowd data, average high temperature 19 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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12°
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
8°
weather_partly_sunny
December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
Monthly weather averages (˚C)

Top landmarks in Chestertown

Washington College

4.1/5 (45 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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Wilmer Park

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

Learn more about Chestertown

Notable for its university life, Chestertown features attractions such as Historical Society of Kent County Maryland and Northern Chesapeake Bay. The city has something for everyone including sights like Chesapeake Bay and Chestertown Historic District within a small-town setting.

See all hotels in Chestertown
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Check out reviews of Chestertown hotels guests love

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"NA"
Mark 7-night trip
Posted 23 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Frequently asked questions

What hotels do travelers recommend in Chestertown?
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown and Driftwood Inn are all properties that our guests really like.
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 24 vacation homes. In addition, you can choose from 6 apartments.
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.