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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 & Accommodations

Driftwood Inn
+1-888-389-4121
609 Washington Ave., Chestertown, MD 21620
  • Cheap Riverfront hotel
  • Check in: 2:00pm
  • Not very comfortable
  • Average value
Holiday Inn Expres & Suites
+1-888-675-2083
150 Scheeler Rd., Chestertown, MD 21620
  • Three Star Suburban property
  • Access to gym on-site
From$90
Very Good 4.0 /5Review Score CallBookMore Details
Red Roof Inn & Suites Chestertown
+1-800-716-8490
160 Scheeler Rd., Chestertown, MD 21620
  • Three Star Rural hotel
  • 3 floors in property
Quality Inn - Grasonville
+1-800-805-5223
101 Vfw Ave., Grasonville, MD 21638 ~18.57 miles southwest of Chestertown
  • Inexpensive Resort hotel
  • 59 rooms in property
Holiday Inn Express Annapolis East / Kent Island
+1-888-965-1860
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.98 miles southwest of Chestertown
  • Midscale Rural hotel
  • Complimentary breakfast is offered
From$180
Very Good 4.0 /5Reviews CallBookMore Details
Best Western Kent Narrows Inn
+1-888-788-5576
3101 Main St., Grasonville, MD 21638 ~19.07 miles southwest of Chestertown
  • Two-star Resort property
  • Fitness / Gym is on-site
  • Good service
  • Most guests said the beds were comfortable
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
  • Check in: 03:00PM
  • Excellent customer service
  • Nice rooms
From$121
Very Good 4.5 /5Review Score 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
  • Check-in time: 3:00PM
From$102
Very Good 4.0 /5Recent Reviews CallBookMore 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
  • Affordable Suburban property
  • Hotel has 120 suites
From$104
Very Good 4.5 /5Hotel Reviews CallBookMore Details
Wye River a Dolce Conference Center in Queenstown
+1-888-734-9421
600 Aspen Dr., Queenstown, MD 21658 ~20.82 miles south of Chestertown
  • High end hotel
Arborview at Riverside in Liriope in Belcamp
+1-888-841-5292
1307 Liriope Court, Belcamp, MD 21017 ~20.95 miles northwest of Chestertown
  • 4 star property
  • Check-in: 4:00 p.m.
Holiday Inn Belcamp Aberdeen Area
+1-888-455-5160
1326 Policy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Three Star Suburban hotel
  • Hotel has 3 floors
Holiday Inn Belcamp - Aberdeen Area - Belcamp
+1-888-965-8297
1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Mid-scale Suburban hotel
  • 3 meeting rooms in property
From$69
Average 3.5 /5Reviews CallBookMore Details
Americas Best Value Inn & Suites Aberdeen
+1-888-906-6358
424 South Philadelphia Blvd., Aberdeen, MD 21001 ~21.04 miles north of Chestertown
  • Low Cost hotel
  • 40 rooms in hotel
Sleep Inn & Suites
+1-888-749-6785
1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • 3 star Suburban hotel
  • Free breakfast
  • Free breakfast bar
  • Room was comfortable and well decorated
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 property
  • Check in: 3:00PM
Ramada Hotel & Conference Center by Wyndham Edgewood
+1-888-389-4485
1700 Van Bibber Rd., Edgewood, MD 21040 ~21.16 miles northwest of Chestertown
  • Low priced Suburban hotel
  • Fitness / Gym is on-site
Candlewood Suites Aberdeen - Edgewood-Bel Air
+1-888-389-4121
4216 Philadelphia Rd., Bel Air, MD 21015 ~21.20 miles northwest of Chestertown
  • Two-star Suburban property
  • Fitness center on property
  • Nice rooms
  • Clean rooms
Extended Stay America Baltimore - Bel Air- Aberdeen : 1361 James Way
+1-888-675-2083
1361 James Way, Bel Air, MD 21015 ~21.23 miles northwest of Chestertown
  • Cheap Highway hotel
  • 3 floors in hotel
Holiday Inn Express Edgewood-Aberdeen-Bel Air : 2118 Emmorton Park Rd.
+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
  • We enjoyed the pool
  • Clean property
From$119
Very Good 4.0 /5Read 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 Cost hotel
  • Hotel has 70 rooms
Quality Inn & Suites Bel Air I 95 - Edgewood
+1-888-965-1860
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Low-priced Suburban property
  • 2 floors in hotel
From$57
Very Good 4.0 /5Read Reviews CallBookMore Details
Quality Inn & Suites Bel Air I-95 Exit 77A
+1-888-788-5576
2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Two-star Suburban hotel
  • Hotel has 40 suites
Homewood Suites by Hilton Bel Air
+1-888-897-9207
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Midscale Suburban property
  • Check in time: 3:00pm
  • Pool is below average
  • Perfectly clean
From$159
Very Good 4.0 /5Reviews 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
  • Check-in: 3:00pm
  • Breakfast is average
  • Average sized rooms
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 Baltimore White Marsh and Quality Inn & Suites Bel Air I-95 Exit 77A 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, Holiday Inn Expres & Suites, 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, The Waterfront 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 Baltimore White Marsh, SpringHill Suites by Marriott Edgewood 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?

Quality Inn & Suites Bel Air I-95 Exit 77A, Sleep Inn & Suites and Quality Inn & Suites Bel Air I 95 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 Aberdeen - Edgewood-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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