5 Star St. Michaels Hotels In 2026

Check prices on hotels in St. Michaels

Sep 22 - Sep 23 Sep 23 - Sep 24 Sep 25 - Sep 27 Oct 2 - Oct 4

Featured St. Michaels 5 Star Hotels

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

The Inn at Tacaro Estate

6220 Town Point Rd Tracys Landing MD

Inn at 202 Dover

202 East Dover Street Easton MD

See all 1,287 properties in St. Michaels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Five Star Hotel Guide for St. Michaels, Maryland

After years of hard work, you deserve nothing less than the royal treatment. We’re talking first-class service, VIP-worthy spa treatments, and luxurious amenities. Thanks to the AARP Travel Center Powered by Expedia, we present you with 5 star AARP hotels in St. Michaels, Maryland, which will provide you with the luxury pampering you crave at rates, which won’t wipe out your retirement funds. Our five star hotels for AARP members and seniors in St. Michaels spoil you to world-class cuisine at on-site restaurants and convenient access to the city’s most popular attractions and must-see sights.

Perhaps you’re traveling to celebrate the freedom of your retirement or to attend your daughter’s wedding, but regardless of the reason for your travels, our St. Michaels hotels with 5 stars for AARP members are certain to complete your perfect getaway. Expedia and ARRP have combined efforts to present you with the best deals and discounts on first-rate accommodations. Browse our selection to find the hottest specials around, because treating yourself to luxury shouldn’t break the bank.