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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

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609 Washington Ave., Chestertown, MD 21620
  • Inexpensive Riverfront property
  • Check-in: 2:00pm
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From$45
Poor 2.0 /5 Latest Reviews Call BookMore Details
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Comfort Inn & Suites Chestertown - Chestertown
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
150 Scheeler Rd., Chestertown, MD 21620 Website
  • Midscale Suburban property
  • Hotel has an eco-friendly policy See policy
More Photos Photo of Comfort Inn & Suites Chestertown
From$90
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Red Roof Inn & Suites Chestertown
+1-800-716-8490

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160 Scheeler Rd., Chestertown, MD 21620
  • Affordable Rural property
  • 3 floors in hotel
More Photos Image of Red Roof Inn & Suites Chestertown
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn in Grasonville
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • 2-star Resort property
  • Free breakfast available
More Photos Image of Quality Inn
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

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1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Three Star Rural property
  • Hotel has 15 rooms
More Photos Exterior of Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
From$180
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Kent Narrows Inn - Grasonville
+1-888-788-5576

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3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • 3 star Resort property
  • 4 floors in hotel
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From$66
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Hilton Garden Inn Kent Island
+1-888-897-9207

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3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Affordable Riverfront hotel
  • 4 meeting rooms in property
More Photos Image of Hilton Garden Inn Kent Island
From$121
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md
+1-888-311-4278

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20 Newton Rd., Aberdeen, MD 21001 ~20.63 miles north of Chestertown
  • Two-star Suburban hotel
  • Hotel has 107 rooms
More Photos Exterior of Home2 Suites by Hilton Baltimore / Aberdeen Md
From$60
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SpringHill Suites Baltimore White Marsh/Middle River : 6110 Greenleigh Ave.
+1-888-469-4795

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6110 Greenleigh Ave., Middle River, MD 21220 ~20.75 miles northwest of Chestertown
  • 3-star Suburban property
  • 4 floors in property
More Photos Exterior of SpringHill Suites Baltimore White Marsh/Middle River
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

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600 Aspen Dr., Queenstown, MD 21658 ~20.82 miles south of Chestertown
  • 4 star property
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From$75
Very Good 4.0 /5 Read Reviews Call BookMore Details
Arborview at Riverside in Liriope in Belcamp
+1-888-841-5292

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1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • Expensive property
  • Hotel has 3 floors
More Photos Photo of Arborview at Riverside in Liriope
From$80
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Holiday Inn Belcamp - Aberdeen Area, an IHG Hotel in Belcamp
+1-888-455-5160

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1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3-star Suburban property
  • 7 suites in property
More Photos Image of Holiday Inn Belcamp - Aberdeen Area, an IHG Hotel
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Americas Best Value Inn & Suites Aberdeen
+1-888-965-8297

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424 South Philadelphia Blvd., Aberdeen, MD 21001 ~21.04 miles north of Chestertown
  • Low Cost property
  • 2 floors in hotel
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From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
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Wingate by Wyndham Bel Air I-95 Exit 77A - Edgewood
+1-888-906-6358

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1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Mid-scale Suburban property
  • 84 sleeping rooms in hotel
More Photos Exterior of Wingate by Wyndham Bel Air I-95 Exit 77A
From$54
Average 3.0 /5 Recent Reviews Call BookMore Details
Motel 6 Edgewood, MD
+1-888-749-6785

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1709 Edgewood Rd., Edgewood, MD 21040 ~21.11 miles northwest of Chestertown
  • Low priced Highway property
  • Gym is available on property
More Photos Photo of Motel 6 Edgewood, MD
From$42
Poor 2.0 /5 Read Reviews Call BookMore Details
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Ramada Hotel & Conference Center by Wyndham Edgewood
+1-888-878-9982

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1700 Van Bibber Rd., Edgewood, MD 21040 ~21.16 miles northwest of Chestertown
  • 2 star Suburban hotel
  • Gym / Fitness Center Available
More Photos Photo of Ramada Hotel & Conference Center by Wyndham Edgewood
From$60
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Extended Stay America Suites Baltimore Bel Air Aberdeen in Bel Air
+1-888-389-4485

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1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low-priced Highway hotel
  • Free breakfast available
More Photos Photo of Extended Stay America Suites Baltimore Bel Air Aberdeen
From$104
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Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel : 2118 Emmorton Park Rd.
+1-888-389-4121

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2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Affordable Suburban property
  • Fitness / Gym is on-site
More Photos Exterior of Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
From$119
Very Good 4.0 /5 Reviews Call BookMore Details
Red Roof Inn Edgewood in Edgewood
+1-888-675-2083

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2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Inexpensive property
  • Check-in: 14:00
More Photos Image of Red Roof Inn Edgewood
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

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
2112a Emmorton Park Rd., Edgewood, MD 21040 Website ~21.27 miles northwest of Chestertown
  • Economy Suburban hotel
  • Fitness + Health Center
More Photos Photo of Quality Inn & Suites Bel Air I-95 Exit 77A
From$57
Average 3.0 /5 Reviews Call BookMore Details
Quality Inn & Suites Bel Air I-95 Exit 77A
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Inexpensive Suburban property
  • Gym / Fitness Center Available
More Photos Exterior of Quality Inn & Suites Bel Air I-95 Exit 77A
From$74
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Hilton Garden Inn Bel Air - Bel Air
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
4160 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Three Star hotel
  • Check-in time: 3:00PM
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From$129
Average 3.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Bel Air
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Affordable Suburban property
  • Free complimentary breakfast
More Photos Image of Homewood Suites by Hilton Bel Air
From$159
Very Good 4.0 /5 Read Reviews Call BookMore Details
SpringHill Suites by Marriott Edgewood/Aberdeen
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Three Star Highway property
  • Complimentary breakfast is offered
More Photos Exterior of SpringHill Suites by Marriott Edgewood/Aberdeen
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

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1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Midscale Rural hotel
  • 2 meeting rooms in property
More Photos Photo of Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
The Inn at Chesapeake Bay Beach Club
+1-888-469-4795

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180 Pier One Rd., Stevensville, MD 21666 ~21.35 miles southwest of Chestertown
  • High-end Suburban hotel
  • 54 rooms in property
More Photos Image of The Inn at Chesapeake Bay Beach Club
From$162
Very Good 4.5 /5 Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South, MD
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.35 miles northwest of Chestertown
  • Affordable Suburban property
  • Hotel has 3 floors
More Photos Exterior of Hampton Inn & Suites Edgewood/Aberdeen-South, MD
From$95
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Candlewood Suites by Ihg in Bel Air
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
4216 Philadelphia Rd., Bel Air, MD 21015 ~21.36 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Hotel has 95 rooms
More Photos Photo of Candlewood Suites by Ihg
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

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
2112b Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • 3-star Suburban hotel
  • Comp. Breakfast
More Photos Image of La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
From$65
Very Good 4.5 /5 Review Score Call BookMore Details
Kent Island Resort : 500 Kent Manor Dr.
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
500 Kent Manor Dr., Stevensville, MD 21666 ~21.59 miles southwest of Chestertown
  • High-end Riverfront property
  • 3 meeting rooms in hotel
More Photos Exterior of Kent Island Resort
From$225
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Super 8 by Wyndham Baltimore/Essex Area
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
98 Stemmers Run Rd., Essex, MD 21221 ~22.10 miles west of Chestertown
  • Cheap Rural property
  • Hotel has 45 rooms
More Photos Image of Super 8 by Wyndham Baltimore/Essex Area
From$65
Not Good 1.0 /5 Guest Reviews Call BookMore Details
Super 8 by Wyndham Joppa : 1015 Pulaski Highway
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
1015 Pulaski Highway, Joppa, MD 21085 ~22.30 miles northwest of Chestertown
  • Two-star Suburban hotel
  • Check in: 16:00
More Photos Exterior of Super 8 by Wyndham Joppa
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

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
1008 Beards Hill Rd., Aberdeen, MD 21001 ~22.49 miles north of Chestertown
  • Inexpensive property
  • 3 floors in hotel
More Photos Image of Super 8 by Wyndham Aberdeen MD
From$59
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Aberdeen - Aberdeen
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.51 miles north of Chestertown
  • 3-star Suburban property
  • 3 conference rooms in property
More Photos Photo of Hilton Garden Inn Aberdeen
From$110
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Aberdeen : 1007 Beards Hill Rd.
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.54 miles north of Chestertown
  • Three Star Highway property
  • 120 rooms in hotel
More Photos Photo of Holiday Inn Express Aberdeen
From$147
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Aberdeen
+1-888-675-2083

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783 West Bel Air Ave., Aberdeen, MD 21001 ~22.56 miles north of Chestertown
  • 2 star Highway hotel
  • Check-in: 11:00 AM
More Photos Image of Days Inn by Wyndham Aberdeen
From$60
Average 3.0 /5 Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen Apg in Aberdeen
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
793 West Bel Air Ave., Aberdeen, MD 21001 ~22.65 miles north of Chestertown
  • Cheap Rural property
  • Free breakfast
More Photos Exterior of La Quinta Inn & Suites by Wyndham Aberdeen Apg
From$109
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
795 West Bel Air Ave., Aberdeen, MD 21001 ~22.66 miles north of Chestertown
  • 2-star Highway property
  • Check in time: 3:00pm
More Photos Image of Hampton Inn & Suites Baltimore/Aberdeen
From$89
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Red Roof Inn Aberdeen in Aberdeen
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
988 Hospitality Way, Aberdeen, MD 21001 ~22.69 miles north of Chestertown
  • 2-star Highway property
  • Check in time: 3pm
More Photos Exterior of Red Roof Inn Aberdeen
From$35
Average 3.0 /5 Read Reviews Call BookMore Details
Travelodge by Wyndham Aberdeen - Aberdeen
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
820 West Bel Air Ave., Aberdeen, MD 21001 ~22.70 miles north of Chestertown
  • Two-star Downtown hotel
  • 2 suites in hotel
More Photos Exterior of Travelodge by Wyndham Aberdeen
From$48
Poor 2.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg : 980 Hospitality Way
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
980 Hospitality Way, Aberdeen, MD 21001 Website ~22.79 miles north of Chestertown
  • Three Star Highway hotel
  • Hotel has 6 meeting rooms
More Photos Exterior of Comfort Inn & Suites Aberdeen Near Apg
From$69
Very Good 4.0 /5 Read Reviews Call BookMore Details
Fairfield Inn N Stes Marriott
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
907 Barnett Lane, Aberdeen, MD 21001 ~22.80 miles north of Chestertown
  • Affordable hotel
  • 4 floors in property
More Photos hotel room
From$90
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore/White Marsh
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
10465 Philadelphia Rd., White Marsh, MD 21162 ~23.01 miles northwest of Chestertown
  • Midscale Suburban hotel
  • Hotel has 108 suites
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From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
830 Long Dr., Aberdeen, MD 21001 ~23.22 miles north of Chestertown
  • 3 star Suburban hotel
  • Hotel has an eco-friendly policy Learn more
More Photos Photo of Residence Inn
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

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
929 Pulaski Highway, Havre De Grace, MD 21078 ~23.64 miles north of Chestertown
  • Cheap Suburban property
  • Hotel has 3 floors
More Photos Photo of Super 8 by Wyndham Havre De Grace Aberdeen Area
From$44
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Woodspring Suites Baltimore White Marsh
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
4985 Mercantile Rd., Nottingham, MD 21236 ~23.78 miles west of Chestertown
  • Economy Suburban property
  • 4 floors in hotel
More Photos Photo of Woodspring Suites Baltimore White Marsh
From$60
Poor 2.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn White Marsh
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
5015 Campbell Blvd., Baltimore, MD 21236 ~23.78 miles west of Chestertown
  • Mid-scale Suburban hotel
  • 155 rooms in property
More Photos Exterior of Hilton Garden Inn White Marsh
From$89
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
8225 Town Center Dr., Nottingham, MD 21236 ~23.80 miles west of Chestertown
  • Mid-scale Suburban property
  • Free breakfast available
More Photos Image of Hampton Inn
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

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
4980 Mercantile Rd., White Marsh, MD 21236 ~23.88 miles west of Chestertown
  • 3 star Suburban property
  • Free breakfast available
More Photos Photo of Residence Inn by Marriott Baltimore White Marsh
From$109
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
8477 Cordon Way, Baltimore, MD 21236 ~23.94 miles west of Chestertown
  • 3-star Suburban hotel
  • Check in time: 3:00 PM
More Photos Exterior of Fairfield Inn & Suites by Marriott White Marsh
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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