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... mapBlack 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... mapCarriage 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... 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 home furnished with period antiques. There are two guest rooms some with fireplaces and a continental breakfast is served each morning. 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 in a traditional style with some antiques. There are four guest rooms available and a full breakfast is included with your stay. 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 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... 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 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. 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 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... mapInn 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... 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 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... mapInn 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... 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 single rooms with private baths, and two suites with private baths. A full breakfast is served each morning. more... mapMoonlight 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... mapOld 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... 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 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. mapSpring 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... 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 and is beautifully furnished in Colonial style. Tea is served daily at 3pm. 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 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.
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
Chestertown, MD,Vacation Rentals By Owner on VRBO®
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HomeAway Vacation Rentals in Chestertown, MD
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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... mapTallulah'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
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. mapMariner'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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