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Chestertown Maryland Hotels & Motels

Find hotels in Chestertown using the list and search tools below. Find discounted hotel accommodations in or close to Chestertown, MD for your upcoming individual or group travel. We list the best Chestertown, Maryland motel and hotel rooms. Browse the Chestertown area hotels to find the perfect lodging! Please use the provided map of the Chestertown hotels. Booking 5+ Rooms? Find Chestertown Group Hotel Discounts

The Chestertown center point is about 21 miles south of Ripken Museum and 21 miles south of Aberdeen Amtrak Station.

Chestertown Hotels/Motels & Accommodations

Driftwood Inn
+1-888-389-4121
609 Washington Ave., Chestertown, MD 21620 +1-888-389-4121
  • Low-priced Riverfront property
  • Hotel has 27 rooms
  • Old furniture
  • Rooms could be cleaner
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Comfort Inn & Suites Chestertown (Former Holiday Inn Express) : 150 Scheeler Rd.
+1-888-675-2083
150 Scheeler Rd., Chestertown, MD 21620 +1-888-675-2083
  • Affordable Suburban hotel
  • 3 floors in hotel
From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Red Roof Inn & Suites Chestertown - Chestertown
+1-800-716-8490
160 Scheeler Rd., Chestertown, MD 21620 +1-800-716-8490
  • 3 star Rural property
  • Hotel has 53 rooms
From$80
Average 3.0 /5 Review Score Call BookMore Details
Quality Inn - Grasonville
+1-800-805-5223
101 Vfw Ave., Grasonville, MD 21638 +1-800-805-5223 ~18.57 miles southwest of Chestertown
  • Two star Resort hotel
  • Free breakfast available
From$74
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Annapolis East / Kent Island
+1-888-965-1860
1020 Kent Narrows Rd., Grasonville, MD 21638 +1-888-965-1860 ~18.98 miles southwest of Chestertown
  • 3 star Rural hotel
  • Free breakfast available
From$180
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Kent Narrows Inn
+1-888-788-5576
3101 Main St., Grasonville, MD 21638 +1-888-788-5576 ~19.07 miles southwest of Chestertown
  • Inexpensive Resort hotel
  • 4 floors in property
  • Most guests said the reception staff was great
  • Easily accessible by car and has restaurants and bars nearby
From$75
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Kent Island : 3206 Main St.
+1-888-897-9207
3206 Main St., Grasonville, MD 21638 +1-888-897-9207 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront hotel
  • 30 suites in property
  • Facilities available
  • Great room
From$121
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore/Aberdeen
+1-888-311-4278
20 Newton Rd., Aberdeen, MD 21001 +1-888-311-4278 ~20.63 miles north of Chestertown
  • Cheap Suburban property
  • Check-in: 3:00PM
  • Clean
  • Tasty breakfast
From$60
Very Good 4.0 /5 Review Score Call BookMore Details
SpringHill Suites Baltimore White Marsh/Middle River
+1-888-469-4795
6110 Greenleigh Ave., Middle River, MD 21220 +1-888-469-4795 ~20.75 miles northwest of Chestertown
  • Three Star Suburban hotel
  • 4 floors in hotel
From$104
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Wye River a Dolce Conference Center
+1-888-734-9421
600 Aspen Dr., Queenstown, MD 21658 +1-888-734-9421 ~20.82 miles south of Chestertown
  • High end property
From$75
Very Good 4.0 /5 Review Score Call BookMore Details
Arborview at Riverside in Liriope in Belcamp
+1-888-841-5292
1307 Liriope Court, Belcamp, MD 21017 +1-888-841-5292 ~20.95 miles northwest of Chestertown
  • High-end property
  • Check-in time: 4:00 p.m.
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Belcamp - Aberdeen Area, an IHG Hotel : 1326 Policy Dr.
+1-888-455-5160
1326 Policy Dr., Belcamp, MD 21017 +1-888-455-5160 ~20.99 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Free comp. breakfast
  • Decent rates
  • Friendly staff
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Americas Best Value Inn & Suites Aberdeen
+1-888-965-8297
424 South Philadelphia Blvd., Aberdeen, MD 21001 +1-888-965-8297 ~21.04 miles north of Chestertown
  • 2-star hotel
  • Check in time: 13:00
From$60
Average 3.0 /5 Review Score Call BookMore Details
Sleep Inn & Suites Edgewood Near Aberdeen Proving Grounds in Edgewood
+1-888-906-6358
1807 Edgewood Rd., Edgewood, MD 21040 +1-888-906-6358 ~21.07 miles northwest of Chestertown
  • Three Star Suburban property
  • 16 suites in property
  • Shower was ok
  • Easily accessible by car and has restaurants and bars nearby
From$54
Average 3.0 /5 Guest Reviews Call BookMore Details
Motel 6 Edgewood Md in Edgewood
+1-888-749-6785
1709 Edgewood Rd., Edgewood, MARYLAND 21040 +1-888-749-6785 ~21.11 miles northwest of Chestertown
  • 2 star Highway hotel
  • Gym is available on property
From$60
Not Good 1.0 /5 Hotel Reviews Call BookMore Details
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Ramada Hotel & Conference Center by Wyndham Edgewood
+1-888-878-9982
1700 Van Bibber Rd., Edgewood, MD 21040 +1-888-878-9982 ~21.16 miles northwest of Chestertown
  • Low-priced Suburban property
  • Free comp. breakfast
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Candlewood Suites Aberdeen - Edgewood-Bel Air, an IHG Hotel - Bel Air
+1-888-389-4485
4216 Philadelphia Rd., Bel Air, MD 21015 +1-888-389-4485 ~21.20 miles northwest of Chestertown
  • Economical Suburban property
  • Fitness center on property
  • Comfortable bed
  • Location is great
From$65
Average 3.0 /5 Hotel Reviews Call BookMore Details
Extended Stay America Suites Baltimore Bel Air Aberdeen
+1-888-389-4121
1361 James Way, Bel Air, MD 21015 +1-888-389-4121 ~21.23 miles northwest of Chestertown
  • Low-priced Highway property
  • 3 floors in hotel
From$104
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
+1-888-675-2083
2118 Emmorton Park Rd., Edgewood, MD 21040 +1-888-675-2083 ~21.23 miles northwest of Chestertown
  • Affordable Suburban hotel
  • Fitness + Health Center
  • Great amenities
  • Most guests said rooms were clean
From$119
Very Good 4.0 /5 Read Reviews Call BookMore Details
Red Roof Inn Edgewood
+1-800-716-8490
2116 Emmorton Park Rd., Edgewood, MD 21040 +1-800-716-8490 ~21.26 miles northwest of Chestertown
  • 2-star property
  • 2 floors in property
From$60
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Quality Inn & Suites Bel Air I-95 Exit 77A : 2112a Emmorton Park Rd.
+1-800-805-5223
2112a Emmorton Park Rd., Edgewood, MD 21040 +1-800-805-5223 ~21.27 miles northwest of Chestertown
  • Inexpensive Suburban hotel
  • Check-in: 3:00 PM
From$57
Average 3.0 /5 Latest Reviews Call BookMore Details
Quality Inn & Suites Bel Air I-95 Exit 77A
+1-888-965-1860
2112a Emmorton Park Rd., Edgewood, MD 21040 +1-888-965-1860 ~21.27 miles northwest of Chestertown
  • Two star Suburban hotel
  • Complimentary breakfast is offered
From$74
Average 3.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Bel Air
+1-888-788-5576
4170 Philadelphia Rd., Bel Air, MD 21015 +1-888-788-5576 ~21.28 miles northwest of Chestertown
  • Affordable Suburban hotel
  • 92 suites in hotel
  • Clean
  • Pillows excellent
From$159
Very Good 4.0 /5 Guest Reviews Call BookMore Details
SpringHill Suites by Marriott Edgewood/Aberdeen
+1-888-897-9207
1420 Handlir Dr., Bel Air, MD 21015 +1-888-897-9207 ~21.29 miles northwest of Chestertown
  • Midscale Highway hotel
  • Free breakfast available
  • Excellent value
  • Breakfast is mediocre
From$106
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Country Inn & Suites by Radisson Bel Air / Aberdeen Md in Bel Air
+1-888-311-4278
1435 Handlir Dr., Bel Air, MD 21015 +1-888-311-4278 ~21.31 miles northwest of Chestertown
  • Affordable Rural property
  • Check-in time: 3pm
  • Spacious rooms
  • Large bathrooms
From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
The Inn at Chesapeake Bay Beach Club - Stevensville
+1-888-469-4795
180 Pier One Rd., Stevensville, MD 21666 +1-888-469-4795 ~21.35 miles southwest of Chestertown
  • 4-star Suburban property
  • Fitness + Health Center
From$162
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South, MD : 2110 Emmorton Park Rd.
+1-888-734-9421
2110 Emmorton Park Rd., Edgewood, MD 21040 +1-888-734-9421 ~21.35 miles northwest of Chestertown
  • Affordable Suburban property
  • 3 floors in property
From$95
Very Good 4.0 /5 Review Score Call BookMore Details
La Quinta Inn & Suites Bel Air I 95 by Wyndham in Edgewood
+1-888-841-5292
2112b Emmorton Park Rd., Edgewood, MD 21040 +1-888-841-5292 ~21.37 miles northwest of Chestertown
  • Mid-scale Suburban property
  • Free breakfast available
From$65
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Kent Island Resort : 500 Kent Manor Dr.
+1-888-455-5160
500 Kent Manor Dr., Stevensville, MD 21666 +1-888-455-5160 ~21.59 miles southwest of Chestertown
  • Four star Riverfront property
  • 24 rooms in hotel
From$225
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Super 8 by Wyndham Baltimore/Essex Area
+1-888-965-8297
98 Stemmers Run Rd., Essex, MD 21221 +1-888-965-8297 ~22.10 miles west of Chestertown
  • Inexpensive Rural hotel
  • Complimentary breakfast is offered
From$65
Not Good 1.0 /5 Read Reviews Call BookMore Details
Super 8 by Wyndham Joppa : 1015 Pulaski Highway
+1-888-906-6358
1015 Pulaski Highway, Joppa, MD 21085 +1-888-906-6358 ~22.30 miles northwest of Chestertown
  • Cheap Suburban property
  • 2 floors in property
From$60
Very Good 4.0 /5 Reviews Call BookMore Details
Super 8 by Wyndham Aberdeen MD
+1-888-749-6785
1008 Beards Hill Rd., Aberdeen, MD 21001 +1-888-749-6785 ~22.49 miles north of Chestertown
  • Economical property
  • Hotel has 62 rooms
  • Quite clean
  • Vibe is not too good
From$59
Average 3.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Aberdeen
+1-888-878-9982
1050 Beards Hill Rd., Aberdeen, MD 21001 +1-888-878-9982 ~22.51 miles north of Chestertown
  • 3-star Suburban property
  • 4 floors in hotel
  • Friendly service
  • Terrific location
From$110
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Aberdeen in Aberdeen
+1-888-389-4485
1007 Beards Hill Rd., Aberdeen, MD 21001 +1-888-389-4485 ~22.54 miles north of Chestertown
  • Three Star Highway property
  • Check in: 3:00 PM
  • Near mall areas
  • Fantastic service
From$147
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Days Inn by Wyndham Aberdeen : 783 West Bel Air Ave.
+1-888-389-4121
783 West Bel Air Ave., Aberdeen, MD 21001 +1-888-389-4121 ~22.56 miles north of Chestertown
  • 2-star Highway property
  • Hotel has 50 rooms
From$60
Average 3.0 /5 Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen-APG
+1-888-675-2083
793 West Bel Air Ave., Aberdeen, MD 21001 +1-888-675-2083 ~22.65 miles north of Chestertown
  • Low priced Rural hotel
  • Free breakfast
  • Clean property
  • Modern Hotel
From$109
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen in Aberdeen
+1-800-716-8490
795 West Bel Air Ave., Aberdeen, MD 21001 +1-800-716-8490 ~22.66 miles north of Chestertown
  • Inexpensive Highway property
  • Complimentary breakfast is offered
From$89
Very Good 4.5 /5 Reviews Call BookMore Details
Red Roof Inn Aberdeen - Aberdeen
+1-800-805-5223
988 Hospitality Way, Aberdeen, MD 21001 +1-800-805-5223 ~22.69 miles north of Chestertown
  • Low-priced Highway property
  • Hotel has 109 rooms
  • Most guests said the wifi quality was great
  • Fantastic service
From$35
Average 3.0 /5 Reviews Call BookMore Details
Travelodge by Wyndham Aberdeen - Aberdeen
+1-888-965-1860
820 West Bel Air Ave., Aberdeen, MD 21001 +1-888-965-1860 ~22.70 miles north of Chestertown
  • Low priced Downtown hotel
  • 2 floors in hotel
  • Nice TV
  • Hallways smelled of smoke
Comfort Inn & Suites Aberdeen
+1-888-788-5576
980 Hospitality Way, Aberdeen, MD 21001 +1-888-788-5576 ~22.79 miles north of Chestertown
  • Three Star Highway property
  • Gym is available on property
From$69
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn N Stes Marriott - Aberdeen
+1-888-897-9207
907 Barnett Lane, Aberdeen, MD 21001 +1-888-897-9207 ~22.80 miles north of Chestertown
  • 3 star hotel
  • Check in time: 15:00
From$90
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites Baltimore White Marsh
+1-888-311-4278
10465 Philadelphia Rd., White Marsh, MD 21162 +1-888-311-4278 ~23.01 miles northwest of Chestertown
  • Three Star Suburban property
  • 108 rooms in hotel
From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Courtyard Aberdeen at Ripken Stadium
+1-888-469-4795
830 Long Dr., Aberdeen, MD 21001 +1-888-469-4795 ~23.33 miles north of Chestertown
  • Three Star Suburban property
  • 2 meeting rooms in property
From$129
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Havre De Grace Aberdeen Area
+1-888-734-9421
929 Pulaski Highway, Havre De Grace, MD 21078 +1-888-734-9421 ~23.64 miles north of Chestertown
  • Low priced Suburban property
  • Hotel has 60 rooms
From$44
Average 3.0 /5 Hotel Reviews Call BookMore Details
Woodspring Suites Baltimore White Marsh
+1-888-841-5292
4985 Mercantile Rd., Nottingham, MD 21236 +1-888-841-5292 ~23.78 miles west of Chestertown
  • 2-star Suburban property
  • Hotel has 122 suites
Hilton Garden Inn White Marsh - Baltimore
+1-888-455-5160
5015 Campbell Blvd., Baltimore, MD 21236 +1-888-455-5160 ~23.78 miles west of Chestertown
  • 3-star Suburban property
  • Hotel has 155 rooms
  • Average beds
  • Room was clean
From$89
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn
+1-888-965-8297
8225 Town Center Dr., Nottingham, MD 21236 +1-888-965-8297 ~23.80 miles west of Chestertown
  • 3-star Suburban property
  • 7 suites in hotel
  • Close to restaurants, bars and shopping areas
  • Bad amenities
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh in White Marsh
+1-888-906-6358
4980 Mercantile Rd., White Marsh, MD 21236 +1-888-906-6358 ~23.88 miles west of Chestertown
  • Midscale Suburban property
  • 4 floors in hotel
  • Awesome vibe
  • Location is great
From$109
Average 3.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh - Baltimore
+1-888-749-6785
8477 Cordon Way, Baltimore, MD 21236 +1-888-749-6785 ~23.94 miles west of Chestertown
  • 3-star Suburban property
  • 116 rooms in property
  • Rooms are ok
  • Average sized rooms
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown in Middletown
+1-888-878-9982
315 Auto Park Dr., Middletown, DE 19709 +1-888-878-9982 ~24.20 miles northeast of Chestertown
  • 3 star Suburban hotel
  • 2 meeting rooms in property
From$70
Very Good 4.5 /5 Recent Reviews Call BookMore Details

Next: See My Chestertown Hotels with Pricing

Graph: Upcoming 20 Days of Chestertown Hotel Rates

Rates shown are nightly rates before taxes and do not necessarily reflect all Chestertown, MD discounts available. The chart reflects the cheapest Chestertown hotel for each day and each star rating category.

FAQs about hotels in Chestertown

What are the best rated hotels in Chestertown?

The Inn at Chesapeake Bay Beach Club, La Quinta Inn & Suites Bel Air I 95 by Wyndham and Kent Island Resort are the best rated hotels based on customer reviews in the last 365 days.

What are the most luxurious hotels in Chestertown?

Wye River a Dolce Conference Center, Arborview at Riverside in Liriope and The Inn at Chesapeake Bay Beach Club are the top 3 luxury hotels near Chestertown city center.

What hotels are closest to the city center of Chestertown?

Driftwood Inn, Comfort Inn & Suites Chestertown (Former Holiday Inn Express), and Red Roof Inn & Suites Chestertown are the properties closest to Chestertown city center.

How much does a cheap hotel in Chestertown cost per night?

In the last year, a 2 star hotel in Chestertown can be as cheap as $96.89 per night. (based on HotelPlanner prices)

How much does a 3 star hotel in Chestertown cost per night?

In the last year, the average 3 star hotel in Chestertown has been $123.00 per night. (based on HotelPlanner prices)

What are the best independent hotels in Chestertown?

The Inn at Chesapeake Bay Beach Club, Kent Island Resort and Arborview at Riverside in Liriope are the best rated independent hotels (not part of a big brand).

What are the most popular Marriott hotels in Chestertown?

SpringHill Suites Baltimore White Marsh, SpringHill Suites by Marriott Edgewood and Fairfield Inn N Stes Marriott are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

What are the most popular Choice Hotels branded hotels in Chestertown?

Comfort Inn & Suites Chestertown (Former Holiday Inn Express), Quality Inn and Comfort Inn & Suites Aberdeen are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the best IHG hotels in Chestertown?

Holiday Inn Exp Stes Middletown, Holiday Inn Express Annapolis East and Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel are the best rated Intercontinental Hotel Group (IHG) branded hotels (based on user reviews score).

Verified reviews of the city of Chestertown

Below are reviews of the city of Chestertown, MD from an actual visitor's perspective.

"Lovely & Picturesque! A Christmas Card Come to Life!"
Score 5.0 / 5

So lovely and picturesque. A Christmas card that came to life. The town, history and water views.

Ann K., from 31-Dec-2021
"Convenient location"
Score 5.0 / 5

Proximity to Rockhall, MD (where the wedding we were attending was.)

Travis W., from 03-Sep-2019
The average traveler rating of the city of Chestertown, MD shown above is 5.0 out of 5 based on 2 reviews
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