Best Boutique Hotels in Saint Michaels
This guide to the best luxury, boutique, and design-forward hotels in Saint Michaels is manually curated by our editorial team based on first-hand research, verified guest reviews, location analysis, and overall service quality. Each hotel is selected to meet high standards of comfort, authenticity, and guest experience.
Located on Maryland’s Eastern Shore, this colonial mansion features a full-service spa, various dining options, and panoramic views of the Chesapeake Bay. The Offshore Sailing School is on-site. Cable TV, free WiFi access, and an iPod dock are featured in every guest room at Inn at Perry Cabin. Decorated in crisp, bright colors and dark wood furnishings, the rooms also have an private bathroom. Guests can relax on the lounge chairs by the outdoor pool or use the fitness center where yoga classes are available. Guests can also stroll through the lush flower gardens and greenhouse at the Inn at Perry Cabin. Overlooking the water, Stars serves breakfast, lunch, and dinner. Enjoy a cocktail by the fireplace at Purser's Pub. Various shops and antique stores in St. Michael’s town center are within 10 minutes’ walk.
Guest Reviews:
- "Food" - "Top hotel with very friendly staff. It exceeded our expectations." - "Everything! Can’t wait to come back for another stay." - "Beautiful location, lovely staff" - "I made bad choices and did not enjoy my breakfast" - "Great location, beautiful property and hotel" - "The grounds were so stunning!" - "Excellent food and options for breakfast." - "PROPERTY WAS BEAUTIFUL, SAILING EXPERIENCE WAS VERY NICE FOOD WAS DELICIOUS STAFF WAS VERY FRIENDLY AND HELPFUL."
Superb
57 reviews
Where a bayside cool retreat awaits: a rebirth of an 1898 original boarding house where watermen ran the docks and crabs were piled high on picnic tables. The Wylder Hotel Tilghman Island, located on a 3-mile island on the Chesapeake Bay, is a remake of an iconic property. It is an all-season escape that honors hardworking fisherman of yesteryear in an irreverent manner. This waterfront hotel makes you feel right at home with its welcoming vibe and great offerings: Tickler’s Crab Shack & Restaurant, Bar Mumbo, a private marina with 25 boat slips, charter fishing trips, and plenty of fun-filled activities. Wylder Hotel Tilghman Island is an awesome location for overnight guests, locals, as well as private gatherings and celebrations. A short drive from Baltimore, Washington D.C. and Philadelphia, Tilghman Island is a relaxed, yet exciting Eastern Shore escape. Drive through St. Michael’s, past the farmland, corn stalks and pumpkin patches, and over the drawbridge across Knapp’s Narrow, and you’ll be on our 3-mile stretch of salty paradise. From charter fishing, to sailing and kayaking, Tilghman Island life is built around the Chesapeake Bay and its bounty of pleasures. Crack your blue crab in the glow of our super-sized sunset, wash it down with a cold one and give yourself a high five from us here at Tilghman Island.
Guest Reviews:
- "The staff were friendly and inviting . Food was good and the rooms clean ." - "The location, the amenities, and the staff." - "Well located with good amentirs" - "Lovely location, relaxed vibe, many amenities." - "The location was fantastic and the food, while pricey, was delicious. The pool was very relaxing. And the grounds were lovely. Although we didn’t use them, there were kayaks, canoes and paddle boards that anyone could use. Maybe next time!"
Very Good
84 reviews
