Shady Side pet-friendly rentals

We found 234 pet-friendly rentals — enter your dates for availability

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any pet-friendly holiday homes in Shady Side?
Stay in one of our three pet-friendly holiday homes in Shady Side and you'll have an ideal base for your next travel adventure with your furry friend. Beverly Beach, Cape Anne and Deale Beach are among the city's most sought-after areas.
How much does it cost to stay in a pet-friendly holiday home in Shady Side?
Where you stay, what time of year you travel and the length of your trip will influence how much you pay for a pet-friendly holiday home in Shady Side. Key in your travel dates on Stayz to easily compare properties and then select the right one for you and your pup.
When is the best time to book a pet-friendly holiday home in Shady Side?
Consider taking a trip to Shady Side in July, when the average temperature is between 22ºC (22ºC) and 30ºC (30ºC). This is the most popular month for Stayz guests to book a pet-friendly holiday home in this well-known destination, which is located in Southern Maryland.
Where can I rent a pet-friendly holiday home with great views?
Enjoy Shady Side from a new perspective when you settle into a pet-friendly holiday home with a view. Book one that's right for you by applying the "Location" and "Recommended" filters. Another fantastic tip? Search for a property that comes with an outdoor area from where you can soak up the views while playing Frisbee with Fido.
Can I book a pet-friendly holiday home near the beach?
Choose a pet-friendly holiday home by the beach in Shady Side and look forward to some seaside fun with your furry friend. Consider staying around Triton Beach or Bay Ridge Beach. These are two great spots for playing ball, tossing a Frisbee or simply relaxing near the shoreline.
Do any pet-friendly holiday homes in Shady Side have a garden?
Some of our pet-friendly holiday homes in Shady Side include an outdoor area for your four-legged friend to run around in. Discover these stays by choosing "Garden or backyard" under the features and amenities filter. Closely read the property details to find out more, such as whether they have a fenced-in yard or are close to dog parks or pet-friendly hiking trails.
Can I book a pet-friendly cabin or lodge in Shady Side?
Grab the leash and take the dog along to one of our pet-friendly cabins or lodges in Shady Side. To find properties where your four-legged friend can also enjoy a holiday in the great outdoors, use our handy "Pet-friendly" filter.
What are the top things to do in Shady Side?
The family will love visiting top-rated attractions like William Paca House and Navy-Marine Corps Memorial Stadium during your trip to Shady Side. If you have energy for an extra stop, Westfield Annapolis Mall is another one for your to-do list. And you won't have to leave Fido behind. Book one of Stayz's pet-friendly holiday homes so every member of your group can enjoy the trip together.