What are the top rated Vacation Rentals in St. Michaels?

There are a lot of options in St. Michaels. If you plan on staying in the St. Michaels area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in St. Michaels: <a href="/property/stay-in-the-heart-of-saint-michaels/HA-3211373700" class="class="static-page-link"">Stay in the HEART of Saint Michaels!</a> <a href="/property/hurry-reserve-your-stay-for-nsummer-fall-of-2025nstr-22-30/HA-3211294816" class="class="static-page-link"">Hurry, reserve your stay for nSummer &amp; Fall of 2025nSTR #22-30</a> <a href="/property/true-in-town-st-michaels-6-acre-waterfront-heated-pool/HA-3211342430" class="class="static-page-link"">TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool</a> <a href="/property/secluded-waterfront-property-on-3-acres-with-swimming-pool-and-dock/HA-1217191326" class="class="static-page-link"">Secluded Waterfront Property on 3 acres with swimming pool and dock.</a> <a href="/property/private-cozy-3br-2ba-1mile-to-historic-downtown-saint-michaels/HA-3212179153" class="class="static-page-link"">Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels</a> <a href="/property/watch-the-ever-changing-sunset-reflect-over-the-eastern-bay/HA-121246578" class="class="static-page-link"">WATCH THE EVER-CHANGING SUNSET REFLECT OVER THE EASTERN BAY</a> <a href="/property/grandview-main-house/HA-321232799" class="class="static-page-link"">Grandview- Main House</a> <a href="/property/waterfront-pier-acreage-to-run-play-pet-friendly-oct-nov-dates-open/HA-3212767076" class="class="static-page-link"">Waterfront - pier &amp; acreage to run &amp; play. Pet friendly Oct/Nov dates open!</a> <a href="/property/minutes-from-downtown-st-michaels-private-dock-kayaks-1000-ft-of-shorelin/HA-1219408012" class="class="static-page-link"">Minutes from Downtown St. Michaels | Private Dock | Kayaks | 1000 Ft of Shorelin</a> <a href="/property/minutes-from-downtown-st-michaels-private-dock-kayaks/HA-1219407068" class="class="static-page-link"">Minutes from Downtown St. Michaels | Private Dock | Kayaks</a>

Which is the best family rental in St. Michaels?

There are many large, family-friendly vacation homes available in St. Michaels; however, here are the most popular family rentals listed on our site: Baydream Believer Waterfront Retreat on Chesapeake Bay in St Michaels Walk to Everything House Baydream Believer

Can we get self-catering vacation rentals in St. Michaels?

Yes, there are 90 self-catering vacation homes in St. Michaels that have hot tubs, swimming pools, & other amenities.

What are the best luxury vacation rentals near St. Michaels?

There are more than 90 luxury villas and vacation homes in or near St. Michaels. Filter by price to compare find the most expensive places to stay on Vacationsrental.