LODGING
Bed & Breakfast, Historic Inns & Hotels
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... 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 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... 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... 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. 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.
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®
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.
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
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
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
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