Cheap Hotels in Chestertown
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Cheap Hotels in Chestertown
No exact matches found, but these alternatives could be just right
Recommended hotels in Chestertown
8.6 out of 10, Excellent, (861)
8.6/10
Excellent
(861)
The price is $104
$104
$115 total
includes taxes & fees
Dec 29 - Dec 30
7.2 out of 10, Good, (421)
7.2/10
Good
(421)
The price is $72
$72
$80 total
includes taxes & fees
Dec 30 - Dec 31
7.8 out of 10, Good, (77)
7.8/10
Good
(77)
The price is $110
$110
$126 total
includes taxes & fees
Dec 25 - Dec 26
10.0 out of 10, Exceptional, (58)
10/10
Exceptional
(58)
The price is $156
$156
$173 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island2.5 star property
Grasonville
7.8 out of 10, Good, (863)
7.8/10
Good
(863)
The price is $84
$84
$94 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG2.5 star property
Grasonville
9.2 out of 10, Wonderful, (939)
9.2/10
Wonderful
(939)
The price is $87
$87
$97 total
includes taxes & fees
Dec 28 - Dec 29
7.6 out of 10, Good, (9)
7.6/10
Good
(9)
The price is $63
$63
$71 total
includes taxes & fees
Dec 25 - Dec 26
9.6 out of 10, Exceptional, (678)
9.6/10
Exceptional
(678)
The price is $110
$110
$122 total
includes taxes & fees
Dec 30 - Dec 31
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MD3.0 star property
Aberdeen
8.8 out of 10, Excellent, (338)
8.8/10
Excellent
(338)
The price is $71
$71
$80 total
includes taxes & fees
Jan 10 - Jan 11, 2026
8.0 out of 10, Very Good, (1000)
8.0/10
Very Good
(1000)
The price is $75
$75
$83 total
includes taxes & fees
Dec 30 - Dec 31
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
9.0/10
Wonderful
(1000)
The price is $114
$114
$127 total
includes taxes & fees
Dec 28 - Dec 29
TownePlace Suites by Marriott Edgewood Aberdeen
TownePlace Suites by Marriott Edgewood Aberdeen3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (95)
9.0/10
Wonderful
(95)
The price is $109
$109
$122 total
includes taxes & fees
Dec 25 - Dec 26
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD3.0 star property
Bel Air
8.8 out of 10, Excellent, (1003)
8.8/10
Excellent
(1003)
The price is $79
$79
$89 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Quality Inn & Suites Bel Air I-95 Exit 77A
Quality Inn & Suites Bel Air I-95 Exit 77A2.5 star property
Edgewood
7.4 out of 10, Good, (1011)
7.4/10
Good
(1011)
The price is $59
$59
$67 total
includes taxes & fees
Dec 25 - Dec 26
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1009)
9.2/10
Wonderful
(1009)
The price is $84
$84
$94 total
includes taxes & fees
Dec 29 - Dec 30
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG2.5 star property
Edgewood
9.0 out of 10, Wonderful, (562)
9.0/10
Wonderful
(562)
The price is $82
$82
$92 total
includes taxes & fees
Dec 26 - Dec 27
9.2 out of 10, Wonderful, (232)
9.2/10
Wonderful
(232)
The price is $98
$98
$109 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Candlewood Suites Aberdeen-Bel Air by IHG
Candlewood Suites Aberdeen-Bel Air by IHG2.5 star property
Bel Air
8.0 out of 10, Very Good, (471)
8.0/10
Very Good
(471)
The price is $83
$83
$93 total
includes taxes & fees
Dec 26 - Dec 27
SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle River2.5 star property
Middle River
9.0 out of 10, Wonderful, (775)
9.0/10
Wonderful
(775)
The price is $107
$107
$124 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area2.5 star property
Edgewood
7.2 out of 10, Good, (1001)
7.2/10
Good
(1001)
The price is $61
$61
$69 total
includes taxes & fees
Dec 30 - Dec 31
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.
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.
Top landmarks in Chestertown
Washington College
Washington College
4/5(13 reviews)
If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.
River Arts Chestertown
River Arts Chestertown
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.
Historical Society of Kent County Maryland
Historical Society of Kent County Maryland
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 Washington College.
Rolphs Wharf Marina
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Wilmer Park
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Crumpton Auction
Crumpton Auction
4.5/5(3 reviews)
Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.
Frequently asked questions
Are there any cheap motels in Chestertown?
If you're eager to find a budget-friendly place to stay in Chestertown, consider booking a motel. Take a look at Driftwood Inn where you'll find free WiFi and free parking.
What are the best cheap things to do in Chestertown?
Sightseeing doesn't have to break the bank. For some things to do in Chestertown, try a visit to attractions like Chestertown Historic District and Wilmer Park during your trip. Be certain a visit to Kings Town Park is in your plans.