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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 - Chestertown
+1-888-389-4121
609 Washington Ave., Chestertown, MD 21620
  • Cheap Riverfront property
  • 27 rooms in property
  • Generally quite dirty
  • Most guests complained about the bathroom
Holiday Inn Expres & Suites in Chestertown
+1-888-675-2083
150 Scheeler Rd., Chestertown, MD 21620
  • 3 star Suburban property
  • Fitness center on property
From$90
Very Good 4.0 /5Read Reviews CallBookMore Details
Quality Suites
+1-800-716-8490
160 Scheeler Rd., Chestertown, MD 21620
  • 3 star Rural hotel
  • 53 rooms in property
Sleep Inn Grasonville : 101 Vfw Ave.
+1-800-805-5223
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Low priced Resort hotel
  • Comp. Breakfast
Holiday Inn Express Annapolis East / Kent Island
+1-888-965-1860
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • 3 star Rural property
  • Check-in time: 3:00pm
From$180
Very Good 4.0 /5Hotel Reviews CallBookMore Details
Best Western Kent Narrows Inn in Grasonville
+1-888-788-5576
3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Economy Resort property
  • Hotel has 4 floors
  • The majority of guests found the staff to be very friendly
  • Bad amenities
From$75
Average 3.5 /5Reviews CallBookMore Details
Hilton Garden Inn Kent Island : 3206 Main St.
+1-888-897-9207
3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • 3-star Riverfront property
  • Check in: 03:00PM
  • Every guests reviewed enjoyed the friendly atmosphere
  • Excellent location
From$121
Very Good 4.5 /5Latest Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen : 20 Newton Rd.
+1-888-311-4278
20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Three Star Suburban property
  • Hotel has 5 floors
From$102
Very Good 4.0 /5Recent Reviews CallBookMore Details
Springhill Suites White Marsh in Middle River
+1-888-469-4795
6110 Greenleigh Ave., Middle River, MD 21220 Website ~20.75 miles northwest of Chestertown
  • Affordable Suburban property
  • Fitness + Health Center
From$104
Very Good 4.5 /5Reviews CallBookMore Details
Wye River a Dolce Conference Center - Queenstown
+1-888-734-9421
600 Aspen Dr., Queenstown, MD 21658 ~20.82 miles south of Chestertown
  • Four-star hotel
Arborview at Riverside in Liriope : 1307 Liriope Court
+1-888-841-5292
1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • 4 star hotel
  • Check in time: 4:00 p.m.
From$80
Average 3.0 /5Reviews CallBookMore Details
Holiday Inn Belcamp : 1326 Policy Dr.
+1-888-455-5160
1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Hotel has 107 rooms
Wingate by Wyndham in Belcamp
+1-888-965-8297
1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Affordable Suburban hotel
  • 3 conference rooms in property
Americas Best Value Inn & Suites Aberdeen - Aberdeen
+1-888-906-6358
424 South Philadelphia Blvd., Aberdeen, MD 21001 ~21.04 miles north of Chestertown
  • Cheap hotel
  • 40 rooms in hotel
Sleep Inn & Suites : 1807 Edgewood Rd.
+1-888-749-6785
1807 Edgewood Rd., Edgewood, MD 21040 Website ~21.07 miles northwest of Chestertown
  • 3 star Suburban hotel
  • 16 suites in hotel
  • Good vibe
  • Tasty breakfast
From$54
Very Good 4.0 /5Reviews CallBookMore Details
Motel 6 Edgewood Md #4886
+1-888-878-9982
1709 Edgewood Rd., Edgewood, MARYLAND 21040 ~21.11 miles northwest of Chestertown
  • 2-star Highway property
  • Gym is available on property
Ramada by Wyndham Edgewood Hotel & Conference Center in Edgewood
+1-888-389-4485
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.16 miles northwest of Chestertown
  • Two star Suburban property
  • Check-in time: 3:00pm
From$60
Average 3.0 /5Reviews CallBookMore Details
Candlewood Suites Bel Air
+1-888-389-4121
4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Low priced Suburban hotel
  • Hotel has 95 rooms
  • Most guests said the reception staff was great
  • Great team
Extended Stay America Baltimore Bel Air
+1-888-675-2083
1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low-priced Highway hotel
  • 101 suites in hotel
Holiday Inn Express - Edgewood
+1-800-716-8490
2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • Three Star Suburban property
  • Free comp. breakfast
  • Breakfast is good
  • Close to restaurants
From$119
Very Good 4.0 /5Review Score CallBookMore Details
Red Roof Inn Edgewood
+1-800-805-5223
2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Low-priced hotel
  • 2 floors in property
Quality Inn & Suites Edgewood Aberdeen
+1-888-965-1860
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • 2 star Suburban hotel
  • Hotel has 20 suites
Comfort Inn & Suites Edgewood Aberdeen - Edgewood
+1-888-788-5576
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Low-priced Suburban property
  • Gym is available on property
From$74
Very Good 4.5 /5Review Score CallBookMore Details
Homewood Suites by Hilton : 4170 Philadelphia Rd.
+1-888-897-9207
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Hotel has 5 floors
  • Pillows excellent
  • Tasty breakfast
From$159
Very Good 4.0 /5Latest Reviews CallBookMore Details
Springhill Suites by Marriott Edgewood Aberdeen
+1-888-311-4278
1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • 3-star Highway property
  • Gym / Fitness Center Available
  • Perfectly clean
  • Dry cereals
From$106
Very Good 4.0 /5Reviews CallBookMore Details
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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 top reviewed hotels in Chestertown?

Hilton Garden Inn Kent Island, Springhill Suites White Marsh and Comfort Inn & Suites Edgewood Aberdeen 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 the Chesapeake Bay Beach Club & Spa are the top 3 luxury hotels near Chestertown city center.

What hotels are closest to the city center of Chestertown?

Driftwood Inn, Holiday Inn Expres & Suites, and Quality Suites 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 the Chesapeake Bay Beach Club & Spa, Historic Kent Manor Inn and Driftwood Inn are the best rated independent hotels (not part of a big brand).

What are the most popular Marriott hotels in Chestertown?

Springhill Suites White Marsh, Springhill Suites by Marriott Edgewood Aberdeen and Courtyard Aberdeen at Ripken Stadium are the best rated Marriott/Starwood branded hotels (based on customer reviews score).

What are the best Choice Hotels branded hotels in Chestertown?

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

What are the most popular IHG hotels in Chestertown?

Holiday Inn Expres & Suites, Holiday Inn Express Annapolis East and Candlewood Suites Bel Air 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.

"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 1 reviews
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