Visitor Guide
Welcome to Chestertown
History on the Waterfront Audio Tour
View Online Bed and Breakfast Availability
Fall Family Weekend Promo
The Hampton Inn of Middletown, DE has rooms available for September 24 with a reduced rate for Washington College of $189
Chestertown, founded in 1706, served as a port of entry during colonial times. The town offers a unique array of shops and restaurants, as well as access to the Chester River, all within walking distance from the College. Chestertown offers students a beautiful setting in which to live and learn!
Whether sitting under a tree enjoying a book on a warm sunny day, canoeing down the Chester River, or sipping cappuccinos with friends at the local coffeehouse, students become part of this community. Chestertown becomes the home away from home for students and alumni!
Only minutes away there are breathtaking escapes to the quiet beaches at Rock Hall and Betterton, while the wildlife refuge at nearby Eastern Neck Island offers the tranquil beauty of a butterfly trail and spectacular sunsets.
Chestertown is also only 90 minutes away from three major cities—Washington, D.C., Baltimore, and Philadelphia—and less than an hour away from Annapolis, Maryland's state capital.
Local Accommodations
Within walking distance of the College
Comfort Suites
160 Scheeler Rd.
Chestertown, MD 21620
410-810-0555
Fax: 410-810-0286
Eastern Shore Vacation Rentals
Multiple Listings
21 S. Harrison Street (office)
Easton, MD 21601
410-770-9093
Hills Inn
114 Washington Avenue
Chestertown, MD 21620
410-778-1926
Rates: $130-150
Holiday Inn Express Hotel and Suites
150 Scheeler Rd.
Chestertown, MD 21620
410-778-0778
The Imperial Hotel
208 High St.
Chestertown, MD 21620
410-778-5000
Simply Bed & Bread
208 Mount Vernon Ave.
Chestertown, MD 21620
410-778-4359
Stepne Manor
406 S. Cross Street
Chestertown, MD 21620
410-810-7591
White Swan Tavern
231 High St.
Chestertown, MD 21620
410-778-2300
Widow's Walk Inn
402 High St.
Chestertown, MD 21620
410-778-6455
5 to 15 minute drive to the College
Brampton Bed and Breakfast Inn
25227 Chestertown Rd. (Rt. 20)
Chestertown, MD 21620
410-778-1860
Brittland Manor
211 Britland Farm Lane
Chestertown, MD 21620
410-810-7591
Claddaugh Farm
160 Claddaugh Ln. (off Rt. 213 South)
Chestertown, MD 21620
410-778-4894
Crow B&B
12441 Vansants Corner Road
Kennedyville, MD 21654
410.648.5687
Great Oak Landing
22170 Great Oak Landing Rd.
Chestertown, MD 21620
410-778-2100
Great Oak Manor House
10568 Cliff Road
Chestertown, MD 21620
1-800-504-3098
Kentfields Farm
5793 Quaker Neck Landing Rd.
Chestertown, MD 21620
410 778-4181
innkeeper@kentfieldsfarm.com
Langford House
7653 Broadneck Road
Chestertown, MD 21620
410-928-3372
Lauretum
954 High Street
Chestertown, MD 21620
410-778-3236
River Lodge
219 Britland Farm Lane
Chestertown, MD 21620
410-810-7591
Running Fox
23791 Ricauds Branch Road
Chestertown, MD 21620
410-810-7591
20-25 minute drive to the College
Bay Breeze Inn
5758 Main St.
Rock Hall, MD 21661
410-639-2061
The Black Duck Inn
1 Chesapeake Ave.
Rock Hall, MD 21661
410-639-2478
Carriage House
5877 Coleman Road
Rock Hall, Maryland 21661
and two-bedroom apartment overlook on 5761 Main Street
410-639-2855
Carrousel Horse
145 N. Main Street
PO Box 237
Galena, MD 21635
410-648-5476
The Cottage
20745 Rock Hall Ave.
Rock Hall, MD 21661
(800) 720-8788 (Gracious Inns)
Hampton Inn
117 Sandhill Drive
Middletown, DE 19709
302-378-5656
Inn at Huntingfield Creek
4928 Eastern Neck Road
Rock Hall, MD 21661
410-639-7779
Inn at Mitchell House
8796 Maryland Pkwy.
Chestertown, MD 21620
410-778-6500
Kitty Knight House
4028 Augustine Herman Hwy
Georgetown, MD 21930
410-648-5200
Mariner's Motel
5681 Hawthorne Ave.
Rock Hall, MD 21620
410-639-2291
Moonlight Bay Inn
6002 Lawton Ave.
Rock Hall, MD 21661
410-639-2660
Napley Green Country Inn
East Neck Island Rd.
Rock Hall, MD 21661
410-639-2267
Old Gratitude House Bed and Breakfast
5944 Lawton Avenue
Rock Hall, Maryland 21661
410-639-7448 or 1-866-846-0724
Osprey Point Yacht Club & Inn
20876 Rock Hall Ave.
Rock Hall, MD 21661
410-639-2194
Queenstown Inn
7109 Main Street
Queenstown, Maryland 21658
888-744-3407
410-827-3396
The River Plantation
Pintail Point
511 Pintail Point Lane
Queenstown, MD 21658
410-827-7029
1-800-697-1777
Rose Tree Bed & Breakfast
116 S. Commerce St.
Centreville, MD 21617
410-758-3991
Rosehill Farm
13842 Gregg Neck Rd.
Galena, MD 21635
410-648-5334
Spring Cove Manor
21060 Spring Cove Road
Rock Hall, Maryland 21661
410-639-2061
Swan Haven
20950 Rock Hall Ave.
Rock Hall, MD
410-639-2527
Swan Point Inn
21658 Wilkens Ave.
Rock Hall, MD 21661
410-639-2500
Tallulah's On Main
5750 Main Street
Rock Hall, Maryland 21661
410-639-2596
30 minutes or more from the College
The Anchorage
5667 Augustine Herman Highway
Cecilton, MD 21913
410-275-8700
Best Western Kent Narrows Inn
3101 Main Street
Grasonville, MD 21638
410-827-6767
bestwesternkninn@guestsinc.com
Comfort Inn
8523 Ocean Gateway
Easton, MD 21601
410-820-8333
Days Inn
7018 Ocean Gateway
Easton, MD 21601
410-822-4600
Hilton Garden Inn Kent Island
3206 Main Street
Grasonville, MD 21638
410-827-3877
Holiday Inn Express
8561 Ocean Gateway
Easton, MD 21601
410-819-6500
Inn at 202 Dover
202 East Dover Street
Easton, MD 21601
866-450-7600
Sleep Inn
101 VFW Ave.
Grasonville, MD 21638
410-827-5555