What are the top rated Pet Friendly Vacation Rentals in Maryland?

There are a lot of options in Maryland. If you plan on staying in the Maryland area, consider making a reservation for a few nights at one of these properties as these have been rated the top Pet Friendly Vacation Rentals in Maryland: <a href="/property/water-front-retreat-sunrise-and-sunset-water-views-lots-of-amenities/HA-321294688" class="class="static-page-link"">Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities</a> <a href="/property/captivating-chesapeake-experience/HA-3212968702" class="class="static-page-link"">Captivating Chesapeake experience</a> <a href="/property/family-and-pet-friendly-waterfront-with-pier/HA-321450640" class="class="static-page-link"">Family and Pet-Friendly, Waterfront with Pier</a> <a href="/property/directly-across-from-usna-gate-one-steps-from-the-waterfront-and-main-street/HA-321655455" class="class="static-page-link"">Directly Across from USNA Gate One &amp; Steps from the Waterfront and Main Street!</a> <a href="/property/boulder-ridge-cabin-a-private-chalet-in-the-woods/HA-3211101831" class="class="static-page-link"">Boulder Ridge Cabin -a private chalet in the woods</a> <a href="/property/rustic-cabin-in-thurmont-md/HA-121193185" class="class="static-page-link"">Rustic Cabin in Thurmont, MD</a> <a href="/property/sunny-escape-2-a-new-era-for-a-well-loved-lake-front-home/HA-1214760443" class="class="static-page-link"">Sunny Escape 2 - A new era for a well loved lake front home</a> <a href="/property/family-friendly-creekside-getaway-hideaway-and-enjoy-the-family-moments/HA-321465337" class="class="static-page-link"">FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS</a> <a href="/property/renovated-apt-in-historic-dist-w-2-parking-spots/HA-3211355581" class="class="static-page-link"">Renovated Apt In Historic Dist w 2 Parking Spots</a> <a href="/property/stunning-views-from-waterfront-log-cabin-with-fireplace-on-the-chesapeake-bay/HA-1214178435" class="class="static-page-link"">Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay</a>

How many pet-friendly vacation rentals are available in Maryland on Trippymates?

There are more than 4930 pet-friendly rentals available on Trippymates. Check prices and availability in Maryland and last updated on January 2026. Check an individual property if they have restrictions on the size or numbers of pets.

Which is the best dog-friendly place to stay in Maryland?

There are many dog-friendly vacation homes available in Maryland. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Maryland: 10 Clarke Hummingbird Inn 240' Private Beachfront @Kent Island Love Point - Great for Families Blue Heron Inn - A Bed and Breakfast LLC

Do you have any luxury vacation homes that allow pets in or near Maryland?

Most definitely! There are many luxury places to stay in Maryland. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Maryland. Though note, more expensive is not always better.