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... mapDriftwood 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 VRBOŽ
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... mapCarrousel 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... mapCladdaugh 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... mapGreat 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... mapGreat 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... mapHill'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... mapImperial 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... mapInn 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... mapLauretum 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... mapRiver 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... mapSimply 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... mapWhite 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... mapWidow'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 VRBOŽ
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
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