Chestertown, Maryland

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Chestertown, Maryland, USA

Lodging in Chestertown, Maryland

Hotels, Lodges, Extended Stay

  • Comfort Suites
    160 Scheeler Road, Chestertown, MD 21620
    410-810-0555, Located just one mile from Washington College, the Comfort Suites in Chestertown offers guests an indoor heated pool, high-speed Internet access, meeting rooms and... more info  map

  • Holiday Inn Express Chestertown
    150 Scheeler Road, Chestertown, MD 21620
    410-778-0778, High-speed wireless Internet, a heated indoor swimming pool and hot tub, fitness center, 24-hour business center, the Express Start breakfast bar, 650 square feet of... more info

  • Imperial Hotel
    208 High Street, Chestertown, MD 21620
    410-778-5000, The Front Room Restaurant & Bar and 11 deluxe rooms and two suites are available at the Imperial Hotel, convenient to shopping, sightseeing and Washington College. more info  map

Bed & Breakfast, Cabins & Cottages

  • Chestertown, MD, on VRBO®
    Renting a private vacation home offers the affordability, exceptional value, and personal attention that you deserve. Most private vacation homes offer considerably more space than you will find in the typical hotel room often at a reduced cost. Now, families can vacation together and still have room to breathe. View their list of vacation rentals now...

  • Brampton Bed & Breakfast Inn
    25227 Chestertown Road, Chestertown, MD 21620
    410-778-1860, A National Register plantation house on Maryland’s Eastern Shore, the award-winning Brampton Bed & Breakfast Inn is a Select Registry lodging establishment that offers... more info  map

  • Great Oak Manor
    10568 Cliff Road, Chestertown, MD 21620
    410-778-5943, Styled after an 18th-century English country retreat, the 12,000 square foot, Georgian-style Great Oak Manor features 12 guest rooms decorated in period themes; with... more info  map

  • Hill's Inn Bed & Breakfast
    114 Washington Avenue, Chestertown, MD 21620
    410-778-1926, Located on one and one thirds acres on a historic residential area near the center of town, this three-story American Gothic-style Victorian home has four guest rooms... more info  map

  • Inn at Mitchell House, The
    8796 Maryland Parkway, Chestertown, MD 21620
    410-778-6500, Situated on 12 manicured acres located less than one mile from the Chesapeake Bay, this lovely 18th century manor home features five guest rooms. A one-bedroom,... more info  map

  • Lauretum Bed & Breakfast Inn
    954 High Street, Chestertown, MD 21620
    410-778-3236, Listed in the National Register of Historic Places, Lauretum Bed & Breakfast Inn offers five guest rooms with private baths. A continental plus breakfast buffet is... more info  map

  • River Inn at Rolph's Wharf Marina, The
    1008 Rolph's Wharf Road, Chestertown, MD 21620
    410-778-6389, Six guest accommodations are available. more info  map

  • Simply Bed & Bread
    208 Mount Vernon Avenue, Chestertown, MD 21620
    Located 100 Yards from Washington College Campus
    410-778-4359, This cozy Cape Cod on Maryland's Eastern Shore, near the Chesapeake Bay; Simply Bed & Bread offers two spacious guest rooms. more info  map

  • White Swan Tavern
    231 High Street, Chestertown, MD 21620
    410-778-2300, The restored, pre-Revolutionary War White Swan Tavern is a bed and breakfast that offers six accommodations with full private baths, central heat and air conditioning,... more info  map

  • Widow's Walk Inn Bed & Breakfast
    402 High Street, Chestertown, MD 21620
    Located in the Historic District
    410-778-6455, Situated on Maryland's Upper Eastern Shore, near the Chester River, Washington College, many historic homes and buildings, gift shops and fine restaurants; Widow's Walk... more info  map

Lodging Guides and Directories

  • BedandBreakfast.com
    is a leading directory of bed and breakfasts, inns, and boutique lodgings throughout Chestertown and neighboring Maryland towns. Shop, compare, and book from their large selection of Chestertown B&B properties with many exclusive deals offered. Gift certificates are also available. BedandBreakfast.com has nearly 7,000 property listings throughout the United States with 50,000 reviews, 80,000 property photos, and interactive maps.

Condos & Vacation Rentals

  • Chestertown, MD,Vacation Rentals By Owner on VRBO%uFFFD
    Renting a private vacation home offers the affordability, exceptional value, and personal attention that you deserve. Most private vacation homes offer considerably more space than you will find in the typical hotel room often at a reduced cost. Now, families can vacation together and still have room to breathe. View their list of vacation rentals now...

  • HomeAway Vacation Rentals in Chestertown, MD
    Forget ordinary hotel rooms! Finding the perfect vacation getaway in Chestertown, MD is easy on HomeAway.com. Choose from 75,000 homes, condos, guesthouses, cottages, and cabins worldwide, and inquire directly with property owners through the site. HomeAway.com vacation rentals offer a unique local experience, often less expensive and more spacious than hotel rooms.

  

Lodging in Chestertown

Towns Near Chestertown