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LODGING

Bed & Breakfast, Historic Inns & Hotels

  • Bay Breeze Inn (circa 1920's)
    5758 Main Street • Rock Hall, MD 21661
    410-639-2061
    The pet-friendly Bay Breeze Inn offers five guest rooms and the Carriage House for guest to enjoy. The fully-furnished Carriage House features one bath, an outside deck, a full kitchen, and open beam ceilings. A full continental breakfast is offered each morning, which guests can enjoy on the rear patio or in the dining room. more...  map

  • Black Duck Inn
    21906 Chesapeake Avenue • Rock Hall, MD 21661
    215-862-5504
    Overlooking the Rock Hall Harbor, this peaceful inn offers five comfortable guest rooms and docking for those arriving by ship. Guest rooms are all well appointed and beautifully decorated. A breakfast basket of fresh coffee, select teas, seasonal fruit, and fresh pastries is delivered to your room.

  • 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 the Brampton Inn, a meticulously restored Greek Revival Plantation House. The inn offers ten guest rooms each with private baths and most with working fireplaces. more...  map

  • Carriage House Bed & Breakfast Inn
    5877 Coleman Road • Rock Hall, MD 21661
    410-639-2855
    Towering over one and a half acres, the Carriage House Inn is just a short walk from the beach, restaurants, and shopping in Rock Hall. The inn offers two guest suites with antiques, queen size beds, and private baths. A full continental breakfast is served each morning in the cafe, Muskrat Alley, located below the inn. 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 home furnished with period antiques. There are two guest rooms some with fireplaces and a continental breakfast is served each morning. 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 in a traditional style with some antiques. There are four guest rooms available and a full breakfast is included with your stay.  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 estate rests alongside the waterfront. With 11 guestrooms, Great Oak offers the finest in a romantic luxury bed and breakfast inn, where all of your whims are cared for, day and night.  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 this three-story American Gothic style Victorian home. There are four guest rooms each with a private bath and decorated with English Victorian antiques. A full breakfast is served each morning along with evening sherry.  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 elegantly decorated guest rooms with Victorian antiques. Each room also features a private bath with heated towel racks. Two luxurious suites are also offered with a continental breakfast served each morning. Restaurant and bar on premises serving lunch, dinner, and Sunday brunch.  more...  map

  • Inn at Huntingfield Creek
    4928 Eastern Neck Road • Rock Hall, MD 21661
    410-639-7779
    Situated on the oldest land parcel in Kent County, this elegant 70-acre estate on the Huntington Inlet is an ideal location to hold small retreats, business conferences and other special occasions. The Inn at Huntingfield Creek offers peaceful accommodations with five guest rooms, one guest cottage, and the four-bedroom Riverhouse, located four miles down the road from the Inn. The Yarmouth Garden Cottage is furnished with a fireplace, full bath, and a well-equipped kitchen. 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 guest rooms and beautifully decorated parlors. A one-bedroom cottage with a fireplace is also available. Guests enjoy a full country breakfast and beverages each day. more...  map

  • Inn at Osprey Point
    20786 Rock Hall Avenue • Rock Hall, MD 21661
    Located on Maryland's Eastern Shore
    410-639-2194
    A full-service destination on the water's edge of Rock Hall, the Inn at Osprey Point offers elegant lodging, gourmet dining, and a world-class marina. The Inn houses seven guest rooms, each with cable television and a private bath. Enjoy a continental breakfast in the morning. The marina offers 160 slips with full length finger piers and hardwood decking. 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 single rooms with private baths, and two suites with private baths. A full breakfast is served each morning. more...  map

  • Moonlight Bay Inn & Marina
    6002 Lawton Avenue • Rock Hall, MD 21661
    Located 12 Miles from Chestertown
    410-639-2660
    Beautifully situated on the Chesapeake Bay, the Moonlight Bay Inn offers 10 rooms decorated in Victorian Queen Anne-style with private baths and fantastic views. Enjoy a full luxurious breakfast and afternoon tea. The marina can house 50 boats on two well-lit docks.  more...  map

  • Old Gratitude House Bed & Breakfast
    5944 Lawton Avenue • Rock Hall, MD 21661
    410-639-7448
    Originally built in a Victorian style about 1890, on the Chesapeake Bay in what was then called Gratitude, the Old Gratitude House Bed & Breakfast houses five beautifully decorated guest rooms and suites with private baths. Its three-bedroom, two-bath home, Rock Hall Retreat, is also available. It is fully furnished and can sleep up to six comfortably, making it perfect for families. A full gourmet breakfast is served each morning.  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 sunsets. Rooms have private baths, central air. Amenities include pool, bar, ships store, full service marina, canoe, pontoon & boat rentals, fishing equipment, private beach & wide lawns.  map

  • Spring Cove Manor
    21060 Spring Cove Road • Rock Hall, MD 21661
    410-639-2061
    As comfortable as a pair of favorite slippers with lots of great things to do (like kayaking, sailing, hiking, birding, bicycling, fishing or just quietly sitting around by the water in front of an old-fashioned (yet very new-fashioned) completely renovated country inn on 8 secluded, wooded and landscaped waterfront acres. Sit in one of their great wicker rockers, looking out over a placid tributary of the Chesapeake Bay, deciding whether to wander through the rustic fishing village of Rock Hall, with its many small shops and delightful restaurants. There are literally hundreds of miles of Chesapeake tributary waterways to explore. They specialize in weddings. Acres of manicured, landscaped lawn provides all the room.  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 and is beautifully furnished in Colonial style. Tea is served daily at 3pm.  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 Chestertown. There are three guest rooms and two suites avialable and a continental breakfast is served each morning.  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.

Lodges

  • 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 modern rooms, a restaurant, and a full service lounge. The lodge is the perfect place for business meetings and conferences, private parties, wedding receptions, hunting parties, or any other group event. Amenities include a full service marina with a fuel dock, swimming pool and hot tub, beach bar with live entertainment on the weekends, a nine hole golf course and other sporting activities, and a well stocked ship store. more...  map

Condos & Vacation Rentals

  •   Chestertown, MD,Vacation Rentals By Owner on VRBO® 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 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.

  •   Rentalo.com Rentalo.com
    saves you time! Click to inquire & compare offers from Vacation Rentals, Hotels, and Bed & Breakfasts in Chestertown, MD. Find the best deals on short term accommodations using this award-winning, traveler-tested website. Browse our extensive inventory offering leisure and business travelers a wide variety of lodging options; from a budget studio to a luxury villa on a private island, from a small boutique hotel or bed and breakfast to a 5 star resort. Find the perfect place to stay for every occasion including family vacations, romantic getaways, business trips, ski, beach or golf vacations.

  • Chestertown, MD, Vacation Rentals on Vacation Rentals.com Chestertown, MD, Vacation Rentals on Vacation Rentals.com
    Are you still making hotel reservations? At VacationRentals.com, customize your next vacation and take advantage of off-season discounts, last minute deals, and freebies! No matter what destination or property type or number of bedrooms you’re looking for, you can find an affordable vacation rental that will suit the needs of you and your fellow travelers. So, what are you waiting for? No matter how tight your budget, you can book your dream vacation on VacationRentals.com today!

  • 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 for daily, weekly, and monthly rental. Each apartment has a living room, kitchen, bedroom, bath, TV, and phone and are located within walking distance to all restaurants and shopping in Chestertown. more...  map

  • Tallulah's on Main
    5750 Main Street • Rock Hall, MD 21661
    410-639-2596
    Close to many antique shops and restaurants in downtown Rock Hall, Tallulah's on Main offers five fully-equipped guest suites and the Beach House. The guest suites vary in size but all come with private baths, full kitchens, heating and air conditioning, ceiling fans, and cable television. The two-bedroom beach property has a comfortable living room, spacious kitchen, full bath, air conditioning, and a washer and dryer. more...  map

Motels/Hotels

  • 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 refrigerator and microwave. Hotel amenities include a heated indoor pool, coffee and tea, and health club privileges.   map

  • Mariner's Motel
    5681 South Hawthorne Avenue • Rock Hall, MD 21661
    410-639-2291
    For over 30 years, the Mariner's Motel has been welcoming guests to the area. All guest rooms include two double beds, telephones, cable TV, refrigerators, coffeemakers, and air conditioning. On-site amenities include a pool, picnic gazebo, dog walk area, laundry facilities, horseshoes, bike rentals, and a playground. more...  map

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