What are the top rated Pet Friendly Vacation Rentals in Oyster Harbor?

There are a lot of options in Oyster Harbor. If you plan on staying in the Oyster Harbor 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 Oyster Harbor: <a href="/property/charming-bay-ridge-cottage-with-chesapeake-bay-views-just-steps-to-the-beach/HA-3214395560" class="class="static-page-link"">Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach</a> <a href="/property/discounted-for-usna-commissioning-week-2024-and-2025-short-term-and-weekends/HA-321379471" class="class="static-page-link"">DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.</a> <a href="/property/charming-annapolis-home-with-cozy-outdoor-hangout/HA-3214599681" class="class="static-page-link"">Charming Annapolis Home with Cozy Outdoor Hangout</a> <a href="/property/pet-friendly-spacious-home-in-annapolis/HA-3214626881" class="class="static-page-link"">Pet-Friendly &amp; Spacious Home in Annapolis</a> <a href="/property/bay-ridge-modern-home-with-vintage-charm/HA-3213323471" class="class="static-page-link"">BAY RIDGE MODERN HOME WITH VINTAGE CHARM</a> <a href="/property/pet-friendly-4-bedrooms-in-annapolis-md-less-than-2-miles-to-naval-academy/HA-3214766084" class="class="static-page-link"">Pet Friendly, 4 Bedrooms in Annapolis, MD less than 2 miles to Naval Academy.</a> <a href="/property/spacious-waterfront-5-bedroom-house-in-charming-annapolis-with-hot-tub/HA-3214857624" class="class="static-page-link"">Spacious Waterfront 5-bedroom house in charming Annapolis with Hot Tub</a> <a href="/property/wonderful-cottage-nestled-on-chesapeake-bay/HA-3214356208" class="class="static-page-link"">Wonderful Cottage Nestled On Chesapeake Bay</a> <a href="/property/charming-annapolis-retreat-with-hidden-wine-room/HA-3214599680" class="class="static-page-link"">Charming Annapolis Retreat with Hidden Wine Room</a> <a href="/property/annapolis-waterfront-dock-ur-boat-walk-2-beach/HA-3213771064" class="class="static-page-link"">Annapolis Waterfront: Dock ur Boat &amp; Walk 2 Beach!</a>

How many pet-friendly vacation rentals are available in Oyster Harbor on Bespokeusatravel?

There are more than 70 pet-friendly rentals available on Bespokeusatravel. Check prices and availability in Oyster Harbor and last updated on December 2025. 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 Oyster Harbor?

There are many dog-friendly vacation homes available in Oyster Harbor. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Oyster Harbor: Charming Annapolis WaterVIEW Home Oasis by the Bay - Waterfront Heated Pool Hot Tub Charming Annapolis WaterVIEW Home Water Views - Close to Downtown Annapolis

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

Most definitely! There are many luxury places to stay in Oyster Harbor. 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 Oyster Harbor. Though note, more expensive is not always better.