
Find hotels in Chestertown, MD from ¥8,382
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Chestertown
Pet friendly
Family friendly
Check prices for these dates
Our top choices for Chestertown hotels

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
7.2 out of 10, Good, (427 reviews)
The price is ¥11,320
¥12,565 total
includes taxes & fees
Feb 15 - Feb 16

The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
7.8 out of 10, Good, (77 reviews)
The price is ¥16,979
¥19,412 total
includes taxes & fees
Mar 1 - Mar 2

Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (873 reviews)
The price is ¥15,903
¥17,652 total
includes taxes & fees
Mar 1 - Mar 2

Super 8 by Wyndham Havre De Grace Aberdeen Area
Super 8 by Wyndham Havre De Grace Aberdeen AreaHavre De Grace
6.6 out of 10, (975 reviews)
The price is ¥8,352
¥9,354 total
includes taxes & fees
Feb 15 - Feb 16

TownePlace Suites by Marriott Edgewood Aberdeen
TownePlace Suites by Marriott Edgewood AberdeenAberdeen
9.0 out of 10, Wonderful, (103 reviews)
The price is ¥20,753
¥23,243 total
includes taxes & fees
Feb 10 - Feb 11

Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.6 out of 10, Exceptional, (712 reviews)
The price is ¥18,552
¥20,593 total
includes taxes & fees
Mar 2 - Mar 3

Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (869 reviews)
The price is ¥13,230
¥14,686 total
includes taxes & fees
Feb 11 - Feb 12

Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (132 reviews)
The price is ¥17,010
¥24,279 total
includes taxes & fees
Feb 10 - Feb 11

Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (959 reviews)
The price is ¥17,609
¥19,546 total
includes taxes & fees
Feb 22 - Feb 23

Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (59 reviews)

The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
9.4 out of 10, Exceptional, (435 reviews)
The price is ¥24,518
¥31,215 total
includes taxes & fees
Feb 10 - Feb 11

Candlewood Suites Aberdeen-Bel Air by IHG
Candlewood Suites Aberdeen-Bel Air by IHGBel Air
8.0 out of 10, Very Good, (481 reviews)
The price is ¥13,206
¥14,790 total
includes taxes & fees
Feb 11 - Feb 12

Super 8 by Wyndham Baltimore/Essex Area
Super 8 by Wyndham Baltimore/Essex AreaEssex
5.6 out of 10, (426 reviews)
The price is ¥11,634
¥13,437 total
includes taxes & fees
Feb 10 - Feb 11

Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very Good, (1,001 reviews)
The price is ¥13,115
¥14,557 total
includes taxes & fees
Feb 15 - Feb 16

Hilton Garden Inn Bel Air
Hilton Garden Inn Bel AirBel Air
9.2 out of 10, Wonderful, (242 reviews)
The price is ¥15,986
¥17,904 total
includes taxes & fees
Feb 20 - Feb 21

Courtyard Aberdeen at Ripken Stadium
Courtyard Aberdeen at Ripken StadiumAberdeen
8.6 out of 10, Excellent, (223 reviews)
The price is ¥13,230
¥14,818 total
includes taxes & fees
Mar 1 - Mar 2

Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,000 reviews)
The price is ¥19,209
¥21,321 total
includes taxes & fees
Feb 15 - Feb 16

SpringHill Suites by Marriott Edgewood/Aberdeen
SpringHill Suites by Marriott Edgewood/AberdeenBel Air
8.8 out of 10, Excellent, (366 reviews)
The price is ¥16,823
¥18,841 total
includes taxes & fees
Feb 20 - Feb 21

Fairfield Inn & Suites by Marriott Aberdeen
Fairfield Inn & Suites by Marriott AberdeenAberdeen
9.0 out of 10, Wonderful, (310 reviews)
The price is ¥17,212
¥19,278 total
includes taxes & fees
Feb 10 - Feb 11
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Stay near popular Chestertown attractions
Learn more about Chestertown
Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

Top Chestertown Hotel Reviews

Americas Best Value Inn Edgewood
10/10 Excellent
More cheap stays in Chestertown

Americas Best Value Inn Edgewood
1709 Edgewood Road Edgewood MD
The price is ¥7,484 per night from Feb 12 to Feb 13
¥7,484
¥8,382 total
Feb 12 - Feb 13
includes taxes & fees
5.6/10 (1,004 reviews)
Frequently asked questions
Explore a world of travel with Expedia
- Resorts in Queenstown
- Family Hotels in Annapolis
- Aberdeen Hotels
- Millington Hotels
- Town Houses in Western Shore of Maryland
- White Marsh Hotels
- Guest Houses in Maryland
- Adults Only Resorts & in Maryland
- B&B in Queenstown
- Ski Hotels in North East
- Luxury Hotels in Annapolis
- Resorts in Aberdeen Proving Ground
- Apartments in Pasadena
- Cheap Hotels in Brooklyn
- Cabin Rentals in Maryland
- Hotels near Queenstown Premium Outlets
- Cheap Hotels in Anchorage
- Cheap Hotels in Pasadena
- Business Hotels in Annapolis
- Rv Parks in Maryland
- Motels in Maryland
- Business Hotels in Pasadena
- Resorts in Kent Island
- Lodges in Annapolis
- Guest Houses in Dundalk
- Hotel with a Concierge Hotels in Baltimore
- Brooklyn Hotels
- Resorts in Pasadena
- Hostels in Maryland
- Green Hotels in Green Haven
- Cheap Hotels in Queenstown
- Cheap Hotels in Maryland
- Farmstay in Queenstown
- Beach Hotels in Maryland
- B&B in Annapolis
- Resorts in Edgewood
- Aparthotels in Abingdon
- Apartments in Centreville
- Harbor East Hotels
- Residences in Belcamp
- Boutique Hotels in Pasadena
- Capsule Hotels in Maryland
- Aparthotels in Belcamp
- Business Hotels in Chestertown
- Resorts in Maryland
- Hotels near Patterson Park
- Aberdeen Proving Ground Hotels
- Hotel Wedding Venues Hotels in Maryland
- B&B in Pasadena
- Hotels near Johns Hopkins Hospital
- Boutique Hotels in Queenstown
- Essex Hotels
- Resorts in Bel Air
- Hotels near Canton Waterfront Park
- Vacation Homes in Belcamp
- Aparthotels in Pasadena
- Fairfield Hotels
- Luxury Hotels in Queenstown
- Boutique Hotels in Brooklyn
- Bel Air Hotels
- Motels in Queenstown
- Hotels near U.S. Naval Academy
- Aparthotels in Anne Arundel County
- Cheap Hotels in Orangeville
- Hotels with Early Check-in in Fells Point
- Holiday Park Resorts in Maryland
- Perry Hall Hotels
- Apartments in Henderson
- Hotel with a Concierge Hotels in Pasadena
- All-Inclusive Hotel Hotels in Maryland
- Waterpark Hotels in Maryland
- Guest Houses in Bel Air
- Romantic Hotels in Pasadena
- Apartments in Essex
- Pasadena Hotels
- Queenstown Hotels
- Aparthotels in Queenstown
- Resorts in Cordova
- Hotels with Early Check-in in Maryland
- Hotels near Ripken Stadium
- Hotels near Bulle Rock Golf Course
- Annapolis Hotels
- Palaces in Annapolis
- Pet-Friendly Hotels in Maryland
- Hotels with Early Check-in in Baltimore
- Queen Anne's County Hotels
- Hotels near National Aquarium in Baltimore
- Hotels near Chesapeake Bay Bridge
- Hotels near Phillips Army Airfield
- Cheap Hotels in Annapolis
- Hotels near Annapolis Maritime Museum
- Hotels near Johns Hopkins Hospital Station
- Green Hotels in West Annapolis
- Edgewood Hotels
- Aparthotels in Aberdeen
- Nottingham Hotels
- Charlestown Hotels
- Hotels near Baltimore Inner Harbor Marina










































































