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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 in Chestertown
+1-888-389-4121
609 Washington Ave., Chestertown, MD 21620
  • Two star Riverfront property
  • Hotel has 27 rooms
  • Beds need improvement
  • Old furniture
Holiday Inn Expres & Suites : 150 Scheeler Rd.
+1-888-675-2083
150 Scheeler Rd., Chestertown, MD 21620
  • Midscale Suburban hotel
  • Check in: 3:00pm
From$90
Very Good 4.0 /5Reviews CallBookMore Details
Quality Suites
+1-800-716-8490
160 Scheeler Rd., Chestertown, MD 21620
  • Mid-scale Rural property
  • Check in time: 3.00 p.m
Sleep Inn Grasonville in Grasonville
+1-800-805-5223
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Cheap Resort hotel
  • 59 rooms in hotel
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
  • 3 meeting rooms in hotel
From$180
Very Good 4.0 /5Guest Reviews CallBookMore Details
Best Western Kent Narrows Inn - Grasonville
+1-888-788-5576
3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Low-priced Resort hotel
  • Hotel has 95 rooms
  • The majority of guests found the staff to be very friendly
  • Every guests reviewed enjoyed the restaurants & bars nearby
From$75
Average 3.5 /5Reviews CallBookMore Details
Hilton Garden Inn Kent Island - Grasonville
+1-888-897-9207
3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Mid-scale Riverfront property
  • 5 floors in property
  • Comfortable beds
  • Excellent location
From$121
Very Good 4.5 /5Latest Reviews CallBookMore Details
Home2 Suites by Hilton Aberdeen
+1-888-311-4278
20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • 3-star Suburban hotel
  • 107 sleeping rooms in hotel
From$102
Very Good 4.0 /5Reviews CallBookMore Details
Springhill Suites White Marsh
+1-888-469-4795
6110 Greenleigh Ave., Middle River, MD 21220 Website ~20.75 miles northwest of Chestertown
  • Affordable Suburban property
  • Hotel has 120 rooms
From$104
Very Good 4.5 /5Guest Reviews CallBookMore Details
Wye River a Dolce Conference Center
+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 property
  • Check-in time: 4:00 p.m.
Holiday Inn Belcamp in Belcamp
+1-888-455-5160
1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Midscale Suburban property
  • 3 floors in hotel
Wingate by Wyndham : 1326 Poilicy Dr.
+1-888-965-8297
1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Check-in time: 3pm
Americas Best Value Inn & Suites Aberdeen
+1-888-906-6358
424 South Philadelphia Blvd., Aberdeen, MD 21001 ~21.04 miles north of Chestertown
  • Cheap hotel
  • Hotel has 2 floors
Sleep Inn & Suites
+1-888-749-6785
1807 Edgewood Rd., Edgewood, MD 21040 Website ~21.07 miles northwest of Chestertown
  • 3-star Suburban property
  • Check in: 11:00 am
  • Terrific location
  • Popular among business travelers
From$54
Very Good 4.0 /5Review Score CallBookMore Details
Motel 6 Edgewood Md #4886
+1-888-878-9982
1709 Edgewood Rd., Edgewood, MARYLAND 21040 ~21.11 miles northwest of Chestertown
  • Economical Highway hotel
  • Check in: 3:00PM
Ramada by Wyndham Edgewood Hotel & Conference Center
+1-888-389-4485
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.16 miles northwest of Chestertown
  • Economy Suburban property
  • Check-in: 3:00pm
Candlewood Suites Bel Air
+1-888-389-4121
4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Economical Suburban hotel
  • 95 rooms in property
  • Pleased with the comfort
  • Most guests said the beds were comfortable
Extended Stay America Baltimore Bel Air in Bel Air
+1-888-675-2083
1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Low Cost Highway property
  • Check in: 3:00pm
Holiday Inn Express in Edgewood
+1-800-716-8490
2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.23 miles northwest of Chestertown
  • 3-star Suburban property
  • Check in time: 3:00 pm
  • Most guests complained about the bathroom
  • Excellent location
From$119
Very Good 4.0 /5Latest Reviews CallBookMore Details
Red Roof Inn Edgewood : 2116 Emmorton Park Rd.
+1-800-805-5223
2116 Emmorton Park Rd., Edgewood, MD 21040 ~21.26 miles northwest of Chestertown
  • Low priced hotel
  • Check in: 14:00
Quality Inn & Suites Edgewood Aberdeen : 2112a Emmorton Park Rd.
+1-888-965-1860
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Low priced Suburban property
  • Hotel has 2 floors
From$57
Very Good 4.0 /5Review Score CallBookMore Details
Comfort Inn & Suites Edgewood Aberdeen in Edgewood
+1-888-788-5576
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Inexpensive Suburban property
  • Complimentary breakfast is offered
Homewood Suites by Hilton in Bel Air
+1-888-897-9207
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Mid-scale Suburban property
  • Fitness center on property
  • Nice breakfast
  • Conveniently located
From$159
Very Good 4.0 /5Recent 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 hotel
  • Check-in: 3:00pm
  • The hotel itself was very nice and clean
  • Excellent value
From$106
Very Good 4.0 /5Latest Reviews CallBookMore Details
Next 25 Chestertown Hotels >  [1 - 25 of 50]    
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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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