Photo by Richard Remington

Woodlawn pet-friendly rentals

We found 26 pet-friendly rentals — enter your dates for availability

Find spaces that suit your style

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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 Woodlawn?
Create new memories with your beloved dog at one of the nine pet-friendly holiday homes in Woodlawn. Stay in this neighbourhood and you'll be within easy reach of top attractions like University of Chicago, Chicago Museum of Science and Industry and Jackson Park.
How much does it cost to stay in a pet-friendly holiday home in Woodlawn?
Prices vary according to the time of year, length of stay and exact location, so key in your trip details to discover what's available. Whatever your plans or budget, Bookabach has pet-friendly holiday homes in Woodlawn for every kind of guest, your four-legged companion included.
When is the best time to book a pet-friendly holiday home in Woodlawn?
March is the most popular month to secure a pet-friendly holiday home in Woodlawn. But the right time to stay depends on you and your furry companion. Besides the weather, also consider if you prefer to travel in the peak season or when things are quieter.
Where can I rent a pet-friendly holiday home with great views?
The only thing that beats relaxing in a pet-friendly holiday home is staying in one that comes with great views. Use our filters to tailor your search for a Woodlawn holiday home with the vistas you want and amenities that'll keep both you and your furry friend happy. Start by selecting "Highly rated for location" under "Property reviews" or fine-tune your results with the "Location" filter.
Can I book a pet-friendly holiday home near the beach?
Let your four-legged friend run off leash at one of our pet-friendly holiday homes by the beach in Woodlawn. Browse our options near popular spots like Oak Street Beach and Ohio Street Beach and spend your days taking long walks along the seashore or playing fetch.
Do any pet-friendly holiday homes in Woodlawn have a garden?
Some of our pet-friendly holiday homes in Woodlawn have an outdoor area for your pooch to run around in. Find 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 an enclosed yard or are close to pet-friendly hiking trails or dog parks.
Can I book a pet-friendly cabin or lodge in Woodlawn?
Grab the leash and take the dog along to one of our pet-friendly cabins or lodges in Woodlawn. To find stays where your four-legged pal can also enjoy the great outdoors, use our "Pet-friendly" filter tool.
What are the top things to do in Woodlawn?
There are plenty of family-friendly sights to explore around Woodlawn, such as Chicago Museum of Science and Industry, Robie House and Jackson Park. With pet-friendly holiday homes for every type of guest, including four-legged ones, Bookabach is the gateway to amazing family adventures.