Chestertown Maryland Lodging

Hotels, Lodges, Extended Stay

• Comfort Suites Chestertown
  160 Scheeler Road • Chestertown, MD 21620
  410-810-0555
  A three story modern hotel offering 53 suites each with a sitting room and a bedroom with a... more...  map

• Driftwood Inn
  609 Washington Avenue • Chestertown, MD 21620
  410-778-3200
  Combining traditional hospitality and luxurious accommodation, they offer guests outstanding... more...

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 Inn (circa 1860)
  25227 Chestertown Road • Chestertown, MD 21620
  410-778-1860
  Listed on the National Register of Historic Places, surround yourself with 19th century decor of... more...  map

• Carrousel Horse Bed & Breakfast (circa 1880)
  145 North Main Street • Chestertown, MD 21635
  14 miles from Chestertown in Galena
  410-648-5476
  Located just one mile from the Sassafras River, The Carrousel Horse is a three-story Colonial-style... more...  map

• Claddaugh Farm Bed & Breakfast (circa 1904)
  160 Claddaugh Lane • Chestertown, MD 21620
  410-778-4894
  Located on eight acres surrounded by farmland sits this three story Victorian farmhouse furnished... more...  map

• Great Oak Landing Lodge
  22170 Great Oak Landing Road • Chestertown, MD 21620
  Fairlee Creek
  410-778-2100
  Perched on a hill with breathtaking views of Fairlee Creek, the Great Oak Landing Lodge offers 28... more...  map

• Great Oak Manor Inn (circa 1938)
  10568 Cliff Road • Chestertown, MD 21620
  410-778-5943
  Tucked away on the outskirts of Chestertown, Maryland, this magnificent 18th century country-style... more...  map

• Hill's Inn Bed & Breakfast (circa 1873)
  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, sits... more...  map

• Imperial Hotel & Restaurant (circa 1903)
  208 High Street • Chestertown, MD 21620
  Historic District
  410-778-5000
  Located in the heart of Chestertown's historic district, this delightful small hotel offers eleven... more...  map

• Inn at Mitchell House, The
  8796 Maryland Parkway • Chestertown, MD 21620
  410-778-6500
  Situated on 10 acres overlooking Stoneybrook Pond, this historic, 18th century home offers six... more...  map

• Lauretum Inn Bed & Breakfast (circa 1881)
  954 High Street • Chestertown, MD 21620
  410-778-3236, 800-742-3236
  This unique, historic Victorian home with gracious porches and a three story staircase offers three... more...  map

• River Inn at Rolph's Wharf (circa 1830)
  1008 Rolph's Wharf Road • Chestertown, MD 21620
  410-778-6347
  Victorian farmhouse on five acres located on the scenic Chester River with spectacular views and... more...  map

• Simply Bed & Bread
  208 Mount Vernon Avenue • Chestertown, MD 21620
  Located 100 Yards from Washington College Campus
  410-778-4359
  Two bright, spacious, allergy-friendly rooms in a cozy 1947 Cape Cod in a great location. Only a... more...  map

• White Swan Tavern
  231 High Street • Chestertown, MD 21620
  Located in the Historic District
  410-778-2300
  Exquisitely decorated with antiques, this 1733 residence was enlarged in 1739 for use as a tavern... more...  map

• Widow's Walk Inn Bed & Breakfast (circa 1877)
  402 High Street • Chestertown, MD 21620
  410-778-6455
  A beautifully furnished clapboard Victorian home that is located in the Historic district of... more...  map

Bed & Breakfast 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®
  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.

• Bittersweet Guest Suites
  239 High Street • Chestertown, MD 21620
  410-778-2300
  Located next door to the White Swan Inn above a downtown shop, these two apartments are available... more...  map