LODGING
Luxury Hotels & Resorts
Bob Pascal's St. Michaels HarbourInn Marina&Spa 
BOOK
101 North Harbor Road • St. Michaels, MD 21663
410-745-9001, 800-955-9001
Within strolling distance to shops, museums and restaurants, the Harbour Inn features 46 lovely waterfront suites and guest rooms, some with jacuzzis and all with thoughtful amenities. The in-house Pascal's Restaurant and Tavern is known for creative preparation and intimate dining. The Spa at Harbour Inn is a full-service resort spa welcoming guests into elegant surroundings where friendly and professional therapists rejuvenate and restore the spirit. Fifty-two slip marina features all the amenities of an upscale resort and conference center. more... mapHarbourtowne Golf Resort & Conference Center
Martingham Drive • St. Michaels, MD 21663
Route 33
410-745-9066, 800-446-9066
This 153 acre resort offers comfortable waterfront guest rooms: six suites feature fireplaces and 24 guest rooms include wood-burning stoves. The resort has meeting space to accommodate groups from 10 to 250, a business center, a fitness center, a pool, and tennis court as well as dining and drinks at the Bayside Restaurant, Club House, Bayside Deck, Duckblind Bar, and the Country Club Lounge.
Bed & Breakfast, Historic Inns & Hotels
Five Gables Inn & Spa BOOK
209 North Talbot Street • St. Michaels, MD 21663
410-745-0100, 877-466-0100
Historic and charming, this luxury inn and spa offers twelve guest rooms and eight suites, all with spa tubs and fireplaces. Your stay includes an expanded continental breakfast, afternoon refreshments, access to the indoor pool, sauna and steam room, fax service and much more. The on-site Aveda concept spa offers multiple treatments designed to relax you. more... map
Old Brick Inn (circa 1816)BOOK
401 South Talbot Street • St. Michaels, MD 21663
410-745-3323
The perfect romantic getaway, serving a lavish full breakfast and offering 14 guest rooms, all with private baths. Some rooms include fireplaces and porches, some are traditional in decor, and other are very unique with distinct themes. The Inn also offers complete conference facilities for meetings, seminars and retreats. more... mapBob Pascal's St. Michaels HarbourInn Marina & Spa
101 North Harbor Road • St. Michaels, MD 21663
410-745-9001
Within strolling distance to shops, museums and restaurants, the Harbour Inn features 46 lovely waterfront suites and guest rooms, some with jacuzzis and all with thoughtful amenities. The in-house Pascal's Restaurant and Tavern is known for creative preparation and intimate dining. The Spa at Harbour Inn is a full-service resort spa welcoming guests into elegant surroundings where friendly and professional therapists rejuvenate and restore the spirit. Fifty-two slip marina features all the amenities of an upscale resort and conference center. mapDr. Dodson House Bed & Breakfast (circa 1799)
200 Cherry Street • St. Michaels, MD 21663-0956
Historic District
410-745-3691
Queen size canopy beds, antique quilts, fireplaces, private bathrooms, and evening hors d'oeuvres served in this historic home. A full breakfast is included with your stay. more... mapGetaway Bed and Breakfast
P.O. Box 928 • St. Michaels, MD 21663
Waterfront Estate
410-745-2094
This secluded waterfront estate offers three guest rooms with king or queen size beds and private baths. Also available is a private English-style guest cottage or a beautiful one-bedroom, second-floor apartment in separate building. A continental breakfast is served. more...Hambleton Inn (circa 1860)
202 Cherry Street • St. Michaels, MD 21663
Located on the harbor
410-745-3350
Distinctive lodging in the heart of St. Michael's, close to restaurants, antique shops, and boutiques, spacious guest rooms at this Inn are tastefully in Ralph Loren decorated and offer private baths, king or queen sized beds, wi/fi, television, air conditioning, and great views of the harbor. Entire inn can be booked for business or weddings. more... mapInn at Perry Cabin Hotel (circa 1812)
308 Watkins Lane • St. Michaels, MD 21663
Located in the Banks of Chesapeake Bay
410-745-2200, 800-722-2949
Housed in a beautiful 19th century mansion, this prestigious inn has been known through generations as the finest hotel on Maryland's Eastern Shore. The Inn at Perry Cabin has 81 guestrooms and suites. Its traditional style is complemented by such modern amenities as access by helicopter, an outdoor pool, and fully equipped conference rooms. Guests can also enjoy fine dining and musical entertainment.Parsonage Inn (circa 1883)
210 North Talbot • St. Michaels, MD 21663
Historic District
410-745-5519
Eight lovely guest rooms with private baths, three with fireplaces, all feature Laura Ashley linens and Queen Ann reproduction furnishings. A full lavish continentals is served. more... mapPoint Breeze Bed & Breakfast
704 Riverview Terrace • St. Michaels, MD 21663
410-745-9563
Come home to the relaxing, comfortable elegance that is Point Breeze. Gracious family home with 400 feet of harbor-side waterfront, two first floor bedrooms, a screen porch, decks and beautiful grounds. A full breakfast is served. more... mapRigby Valliant House Bed & Breakfast (circa 1832)
123 West Chestnut Street • St. Michaels, MD 21663
410-745-5647
Lovingly restored, guest room amenities at this bed and breakfast include refrigerators stocked with refreshments, fruits, fresh baked pastries, cereals and hot beverages. This location also offers a hot tub, free guest parking, nearby golf and non-smoking rooms. Children are welcome, but no pets. mapTarr House Bed & Breakfast (circa 1867)
109 Green Street • St. Michaels, MD 21663
410-745-2175
Built in 1667, Tarr House Bed & Breakfast offers two lovely rooms on a quiet street overlooking the St. Michaels Harbor. A full gourmet breakfast is included on your stay. map
Bed & Breakfast Guides and Directories
BedandBreakfast.com
is a leading directory of bed and breakfasts, inns, and boutique lodgings throughout neighboring Maryland towns. Shop, compare, and book from their large selection of 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.
Cabins & Cottages
Eastern Shore Vacation Rentals
28282 St. Michaels Road • St. Michaels, MD 21601
410-770-9093
Eastern Shore Vacation Rentals offers a large portfolio of cottages, vacation homes and estates on Maryland's Eastern Shore. Weekly, weekends or seasonal rentals are available. more... mapGrandview At Pleasure Point
6601 Bozman Neavitt Road • Neavitt, MD 21652
717-392-4876
Private five and a half acre Victorian Country Estate with 4 bedroom main house, a 2 bedroom cottage, and 2-1 bedroom units in a second cottage. There are two and a half piers, 1,300 feet of waterfront, an inground pool, boat house, fireplaces, poster beds, and newly renovated cottages. Grandview sleeps a total of 13 in the Main House, 6 in the two bedroom and 4 in each 1 bedroom. A row boat per unit is available. more... map
Condos & Vacation Rentals
St. Michaels, 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 St. Michaels, MD
Forget ordinary hotel rooms! Finding the perfect vacation getaway in St. Michaels, 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 St. Michaels, 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.
St. Michaels, MD Vacation Rentals by AlwaysOnVacation.com
Find the perfect vacation rental to match your budget without compromising on luxury and comfort. Search from a wide selection of vacation homes, villas, condos and other property types. Browse photos, rates, availability and book properties directly from owner in St. Michaels and surrounding areas.
St. Michaels, 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!Tidewater Vacations
207A South Talbot Street • St. Michaels, MD 21663
410-745-5255
Offers a fine selection of vacation rental homes near St. Michaels, Maryland, on the Eastern shore of the Chesapeake Bay. more... map
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