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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 : 609 Washington Ave.
+1-888-389-4121
609 Washington Ave., Chestertown, MD 21620
  • Inexpensive Riverfront property
  • Check-in: 2:00pm
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Comfort Inn & Suites Chestertown - Chestertown
+1-888-675-2083
150 Scheeler Rd., Chestertown, MD 21620 Website
  • Midscale Suburban property
  • Hotel has an eco-friendly policy See policy
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Red Roof Inn & Suites Chestertown
+1-800-716-8490
160 Scheeler Rd., Chestertown, MD 21620
  • Affordable Rural property
  • 3 floors in hotel
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn in Grasonville
+1-800-805-5223
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • 2-star Resort property
  • Free breakfast available
From$74
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel in Grasonville
+1-888-965-1860
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Three Star Rural property
  • Hotel has 15 rooms
From$180
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Kent Narrows Inn - Grasonville
+1-888-788-5576
3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • 3 star Resort property
  • 4 floors in hotel
From$66
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Kent Island
+1-888-897-9207
3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront hotel
  • 4 meeting rooms in property
From$121
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md
+1-888-311-4278
20 Newton Rd., Aberdeen, MD 21001 ~20.63 miles north of Chestertown
  • Two-star Suburban hotel
  • Hotel has 107 rooms
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
SpringHill Suites Baltimore White Marsh/Middle River : 6110 Greenleigh Ave.
+1-888-469-4795
6110 Greenleigh Ave., Middle River, MD 21220 ~20.75 miles northwest of Chestertown
  • 3-star Suburban property
  • 4 floors in property
From$104
Very Good 4.0 /5 Review Score Call BookMore Details
Wye River a Dolce Conference Center : 600 Aspen Dr.
+1-888-734-9421
600 Aspen Dr., Queenstown, MD 21658 ~20.82 miles south of Chestertown
  • 4 star property
From$75
Very Good 4.0 /5 Read Reviews Call BookMore Details
Arborview at Riverside in Liriope in Belcamp
+1-888-841-5292
1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Expensive property
  • Hotel has 3 floors
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Belcamp - Aberdeen Area, an IHG Hotel in Belcamp
+1-888-455-5160
1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3-star Suburban property
  • 7 suites in property
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Americas Best Value Inn & Suites Aberdeen
+1-888-965-8297
424 South Philadelphia Blvd., Aberdeen, MD 21001 ~21.04 miles north of Chestertown
  • Low Cost property
  • 2 floors in hotel
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Wingate by Wyndham Bel Air I-95 Exit 77A - Edgewood
+1-888-906-6358
1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Mid-scale Suburban property
  • 84 sleeping rooms in hotel
From$54
Average 3.0 /5 Recent Reviews Call BookMore Details
Motel 6 Edgewood, MD
+1-888-749-6785
1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low priced Highway property
  • Gym is available on property
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Ramada Hotel & Conference Center by Wyndham Edgewood
+1-888-878-9982
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.16 miles northwest of Chestertown
  • 2 star Suburban hotel
  • Gym / Fitness Center Available
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Extended Stay America Suites Baltimore Bel Air Aberdeen in Bel Air
+1-888-389-4485
1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low-priced Highway hotel
  • Free breakfast available
From$104
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel : 2118 Emmorton Park Rd.
+1-888-389-4121
2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Affordable Suburban property
  • Fitness / Gym is on-site
From$119
Very Good 4.0 /5 Reviews Call BookMore Details
Red Roof Inn Edgewood in Edgewood
+1-888-675-2083
2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Inexpensive property
  • Check-in: 14:00
From$60
Very Good 4.0 /5 Review Score Call BookMore Details
Quality Inn & Suites Bel Air I-95 Exit 77A
+1-800-716-8490
2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Economy Suburban hotel
  • Fitness + Health Center
From$57
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn & Suites Bel Air I-95 Exit 77A
+1-800-805-5223
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Inexpensive Suburban property
  • Gym / Fitness Center Available
From$74
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Bel Air - Bel Air
+1-888-965-1860
4160 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Three Star hotel
  • Check-in time: 3:00PM
From$129
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 ~21.28 miles northwest of Chestertown
  • Affordable Suburban property
  • Free complimentary breakfast
From$159
Very Good 4.0 /5 Read Reviews Call BookMore Details
SpringHill Suites by Marriott Edgewood/Aberdeen
+1-888-897-9207
1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Three Star Highway property
  • Complimentary breakfast is offered
From$106
Very Good 4.0 /5 Read Reviews Call BookMore Details
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD - Bel Air
+1-888-311-4278
1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Midscale Rural hotel
  • 2 meeting rooms in property
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
The Inn at Chesapeake Bay Beach Club
+1-888-469-4795
180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • High-end Suburban hotel
  • 54 rooms in property
From$162
Very Good 4.5 /5 Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South, MD
+1-888-734-9421
2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.35 miles northwest of Chestertown
  • Affordable Suburban property
  • Hotel has 3 floors
From$95
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Candlewood Suites by Ihg in Bel Air
+1-888-841-5292
4216 Philadelphia Rd., Bel Air, MD 21015 ~21.36 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Hotel has 95 rooms
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
+1-888-455-5160
2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Comp. Breakfast
From$65
Very Good 4.5 /5 Review Score Call BookMore Details
Kent Island Resort : 500 Kent Manor Dr.
+1-888-965-8297
500 Kent Manor Dr., Stevensville, MD 21666 ~21.59 miles southwest of Chestertown
  • High-end Riverfront property
  • 3 meeting rooms in hotel
From$225
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Super 8 by Wyndham Baltimore/Essex Area
+1-888-906-6358
98 Stemmers Run Rd., Essex, MD 21221 ~22.10 miles west of Chestertown
  • Cheap Rural property
  • Hotel has 45 rooms
From$65
Not Good 1.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Joppa : 1015 Pulaski Highway
+1-888-749-6785
1015 Pulaski Highway, Joppa, MD 21085 ~22.30 miles northwest of Chestertown
  • Two-star Suburban hotel
  • Check in: 16:00
From$60
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Super 8 by Wyndham Aberdeen MD : 1008 Beards Hill Rd.
+1-888-878-9982
1008 Beards Hill Rd., Aberdeen, MD 21001 ~22.49 miles north of Chestertown
  • Inexpensive property
  • 3 floors in hotel
From$59
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Aberdeen - Aberdeen
+1-888-389-4485
1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.51 miles north of Chestertown
  • 3-star Suburban property
  • 3 conference rooms in property
From$110
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Aberdeen : 1007 Beards Hill Rd.
+1-888-389-4121
1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.54 miles north of Chestertown
  • Three Star Highway property
  • 120 rooms in hotel
From$147
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Aberdeen
+1-888-675-2083
783 West Bel Air Ave., Aberdeen, MD 21001 ~22.56 miles north of Chestertown
  • 2 star Highway hotel
  • Check-in: 11:00 AM
From$60
Average 3.0 /5 Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen Apg in Aberdeen
+1-800-716-8490
793 West Bel Air Ave., Aberdeen, MD 21001 ~22.65 miles north of Chestertown
  • Cheap Rural property
  • Free breakfast
From$109
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen
+1-800-805-5223
795 West Bel Air Ave., Aberdeen, MD 21001 ~22.66 miles north of Chestertown
  • 2-star Highway property
  • Check in time: 3:00pm
From$89
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Red Roof Inn Aberdeen in Aberdeen
+1-888-965-1860
988 Hospitality Way, Aberdeen, MD 21001 ~22.69 miles north of Chestertown
  • 2-star Highway property
  • Check in time: 3pm
From$35
Average 3.0 /5 Read Reviews Call BookMore Details
Travelodge by Wyndham Aberdeen - Aberdeen
+1-888-788-5576
820 West Bel Air Ave., Aberdeen, MD 21001 ~22.70 miles north of Chestertown
  • Two-star Downtown hotel
  • 2 suites in hotel
Comfort Inn & Suites Aberdeen Near Apg : 980 Hospitality Way
+1-888-897-9207
980 Hospitality Way, Aberdeen, MD 21001 Website ~22.79 miles north of Chestertown
  • Three Star Highway hotel
  • Hotel has 6 meeting rooms
From$69
Very Good 4.0 /5 Read Reviews Call BookMore Details
Fairfield Inn N Stes Marriott
+1-888-311-4278
907 Barnett Lane, Aberdeen, MD 21001 ~22.80 miles north of Chestertown
  • Affordable hotel
  • 4 floors in property
From$90
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore/White Marsh
+1-888-469-4795
10465 Philadelphia Rd., White Marsh, MD 21162 ~23.01 miles northwest of Chestertown
  • Midscale Suburban hotel
  • Hotel has 108 suites
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn
+1-888-734-9421
830 Long Dr., Aberdeen, MD 21001 ~23.22 miles north of Chestertown
  • 3 star Suburban hotel
  • Hotel has an eco-friendly policy Learn more
From$179
Average 3.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Havre De Grace Aberdeen Area : 929 Pulaski Highway
+1-888-841-5292
929 Pulaski Highway, Havre De Grace, MD 21078 ~23.64 miles north of Chestertown
  • Cheap Suburban property
  • Hotel has 3 floors
From$44
Average 3.0 /5 Read Reviews Call BookMore Details
Woodspring Suites Baltimore White Marsh
+1-888-455-5160
4985 Mercantile Rd., Nottingham, MD 21236 ~23.78 miles west of Chestertown
  • Economy Suburban property
  • 4 floors in hotel
Hilton Garden Inn White Marsh
+1-888-965-8297
5015 Campbell Blvd., Baltimore, MD 21236 ~23.78 miles west of Chestertown
  • Mid-scale Suburban hotel
  • 155 rooms in property
From$89
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn
+1-888-906-6358
8225 Town Center Dr., Nottingham, MD 21236 ~23.80 miles west of Chestertown
  • Mid-scale Suburban property
  • Free breakfast available
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh : 4980 Mercantile Rd.
+1-888-749-6785
4980 Mercantile Rd., White Marsh, MD 21236 ~23.88 miles west of Chestertown
  • 3 star Suburban property
  • Free breakfast available
From$109
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh
+1-888-878-9982
8477 Cordon Way, Baltimore, MD 21236 ~23.94 miles west of Chestertown
  • 3-star Suburban hotel
  • Check in time: 3:00 PM
From$89
Very Good 4.0 /5 Read 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 by Wyndham Bel Air 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, 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, Quality Inn and Comfort Inn & Suites Aberdeen Near Apg are the best rated Choice Hotels branded hotels (based on HotelPlanner reviews score).

What are the most popular IHG hotels in Chestertown?

Holiday Inn Express Annapolis - Kent Island, an IHG Hotel, Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel and Holiday Inn Express Aberdeen 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.

"The water and relaxed nature of the area."
Score 4.0 / 5

The water, buildings, friendliness, and relaxed nature.

Margie H., from 23-Jul-2022
"Clean & Safe"
Score 4.0 / 5

Clean and safe.

Henry Y., from 21-Jun-2022
"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 4.5 out of 5 based on 4 reviews
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