Find Business Hotels in Chestertown, MD

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Check availability on Chestertown Business Hotels

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Chestertown business-friendly hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (861)
"Everything was well!"
United States
Ahmed
The price is ￥15,771
￥17,507 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn & Suites Chestertown
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, (95)
"Spotless, very good "
United States
Efrain
The price is ￥17,019
￥19,063 total
includes taxes & fees
Dec 28 - Dec 29
TownePlace Suites by Marriott Edgewood Aberdeen
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, (339)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
The price is ￥11,170
￥12,512 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Free daily self-serve breakfast
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1002)
"Great stay"
United States
Edward
The price is ￥10,618
￥11,786 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Quality Inn Smyrna
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, (939)
"It was very comfortable and clean"
United States
Maria
The price is ￥12,335
￥13,692 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (472)
"Good room and service "
United States
Robert
The price is ￥12,960
￥14,514 total
includes taxes & fees
Dec 29 - Dec 30
Candlewood Suites Aberdeen-Bel Air by IHG
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (606)
"very pet friendly!!"
United States
larry
The price is ￥15,350
￥17,192 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hampton Inn & Suites Baltimore/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, (1000)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is ￥12,366
￥13,850 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1003)
"Room was great staff friendly"
United States
Melissa
The price is ￥13,060
￥14,626 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1001)
"Nice place"
United States
Maria
The price is ￥13,935
￥15,607 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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 properties

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The chef was amazing"
Karla 1-night trip
Posted 4 days ago
Hilton Garden Inn Baltimore/White Marsh

Frequently asked questions

How much do business-friendly hotels in Chestertown cost?
Prices for business hotels in Chestertown range between ￥11,786 and ￥19,063 per night. Whatever your budget, Expedia will help you locate the ideal place to complete the job. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels in Chestertown that are also business friendly?
Comfort Inn & Suites Chestertown is the perfect mix of work and play. This 2.5-stars Chestertown property is family friendly and features complimentary breakfast and WiFi. When it's time to squeeze in some business, you'll find the conveniences you need to be comfortable and productive. When you've finished work, there are lots of family-friendly attractions to discover around Chestertown. Historical Society of Kent County Maryland and River Arts Chestertown are two popular options.
Why book your business-friendly hotel in Chestertown with Expedia?
Here at Expedia, we make it our job to help you find a suitable stay at the right price. From 5-star corporate-friendly properties to affordable motor inns loaded with amenities, you'll have your next work trip arranged in a few simple clicks.
How can I find cheap business-friendly hotels in Chestertown?
Expedia can help you easily find cheap business-friendly hotels in Chestertown. Head to our "traveler experience" filter and click on "business friendly." This will show you properties with amenities designed to help you work comfortably and effectively, like included breakfast and free WiFi. You can also choose your preferred star rating and budget to keep costs to a minimum.
What is there to do in Chestertown near my business-friendly hotel?
The best travel accessory is a well-planned to-do list. Historical Society of Kent County Maryland is a good place to begin your sightseeing in Chestertown.

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