Pet Sitting & Drop Ins in Silver Spring, Milwaukee, WI
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Silver Spring pet sitters
“Anya is AMAZING! She has so much availability and is very responsive. She is absolutely wonderful to my sweet Lily! Even for drop in visits she always lets her out and then stays to play with Lily for a while! I could not recommend her enough!”

About: I got my first pet-sitting gig when I was 8 years old, feeding my neighbor’s cat. I had multiple farm jobs as a teen and have experience with a variety of species. I have worked for the Wisconsin Humane Society as an animal care technician and as a veterinary assistant at a Spay/Neuter clinic. I have received behavioral training for reactive and nervous dogs, and am willing to work with difficult animals. My schedule is very open and I have a lot of flexibility! I was badly injured last year and have been on extended leave from my career so I have had lots of time to dote on my three dogs and take on new Rover clients! Working with dogs has done so much for my healing process physically and mentally. I have a dream of starting a non-profit dog walking service for struggling teens and young adults one day and try to spread some of that healing around! When I’m building a relationship with a new dog I engage with them on a respectful level- meet them where they’re at and take the time to get to know their personalities, likes and dislikes. Their comfort and safety are paramount. I use positive reinforcement methods only, building trust with animals is more important to me than perfect obedience :)
“Katie was great with my kitty. She put a lot of effort into making my cat feel safe and entertained while visiting. The pictures she shared were adorable, my cat was obviously having a great time with Katie!”

About: Hello and welcome! We take care of/have taken care of all different kinds of pets. We have our own two dogs, as well as six cats. We have experience with multiple different breeds and types of animals, as well as being able to handle many at a time. (We have had up to 9 dogs in my care at one time!) I know how hard it is to leave your pet behind, which is why I will update you with pictures as much as you would like. I have a finished basement if your loved one would prefer to be separated, and also have many open rooms for them to choose from for slumber. The cats have a gated off cat room, only accessible to humans and kitties. The crew and I can't wait to meet you! (Or if you prefer the whole crew won't meet you :)). Dani is currently home full time. At this time Dani is home for almost the entire day, with occasional errands. You can request our schedule for any amount of time to confirm your loved one will be cared for properly and on time. We deep clean all items used after a pet stays, so that they are ready for the next pet to stay. We have extra blankets, beds, crates, bowls, and more. We keep our fishtanks neat and clean, as well as my home. My dogs are extremely friendly even with cats. My backyard is fenced in with access through a back door. When it's nice out we play outside with the dogs where they have access to a kiddie pool to play in the water. I have started to add more outdoor play equipment/toys.
About: Hi! We’re Maddie & Joseph — a pet-loving couple with a lifestyle built around dogs. We offer a calm, loving, and active environment where your dog is part of the family. I (Maddie) have grown up with dogs and cats my entire life and have always been hands-on with training. My grandpa has been breeding huskies since before I was born so dogs have always been a large part of my life. . I’m confident working with high-energy and large breeds, and I’m especially passionate about giving puppies the structure, love, and attention they need. I previously worked at a doggy daycare which has given me plenty of knowledge on caretaking and maintaining a happy and healthy home with multiple dogs. I (Joseph) have been learning to train service dogs for almost two years and currently work with clients in our neighborhood. I’ve always had a deep love for animals—I raised a kitten growing up and worked at a reptile store where I cared for reptiles, fish, and insects before traveling for a year. Together, we’re all about giving pets thoughtful, experienced, personalized care every step of the way. 🐾 We are both currently working from home so normally one of us is always home. If we do leave your pup will never be left alone for more than an hour. Our space includes a fully fenced backyard, a dedicated doggy room with a queen-sized mattress, cozy dog beds, and an XL crate if needed. Ring cameras and security system so we know our house is always watched. Maddie has trained her super well-mannered and playful 6-year-old Siberian Husky since birth who loves making new friends. We only take in 2-3 dogs at a time which is plenty of space for our house. Our neighborhood is quiet and safe with a playground, large field and lots of kids around. We follow your dog’s routine closely and send regular updates so you always feel connected—your pup will be treated like part of the family. 🐾
“Shelby took care of Mickey for a week. She followed his daily routine and kept us posted if there were changes, I.e. not going to potty when it was raining. Mickey gets anxious and sad when we leave, but Mickey was happy and evidently less stressed/anxious when we returned. Thank you Shelby!”

About: I've grown up with pets ever since I was little. I've been trusted even from young ages to walk, feed, and clean up after dogs. I've never had a bad experience and I'm always willing to encounter any and every kind of dog out there with lots of love and care! I have my own pet at home, had him for 10 years. Even after so long, it's so easy and even fun sometimes to do the little things for your pets like feeding them, walking them, and just making sure you spend some quality time with them! There's never a moment I don't want to be around my pet, or any pet for that matter! I always think the key to good pet care is real love and attention. Watching for what your pets want and giving them it will make them happy. If it's attention, bring on the cuddles! If it's a walk, let's do it! And that goes for pets that aren't mine as well. I always care for them like they're mine, and will pay attention to what they want as well as what their owners know is best too!
About: I have been around dogs my whole life. I grew up on a farm and we always had three dogs around. I frequently pet sit for my friend's 60 pound Pitt-mix. I can give medication, and am good with puppies. I can patiently train or work with dogs who are learning the ropes. I can provide daily exercise when your dog is with me, and lots of snuggles! I work less than ten miles from home, so on most days I can pop in for a walk or potty break. I can board the same dog for up to two weeks depending on the situation. I can only take one dog at a time so your dog will get all the attention! I always follow the owner's wishes, and guidance on how to best care for their pet. I don't go overboard with treats, but I do go overboard with affection.

“Cindy took great care of our dog and sent great pictures of him playing. I feel confident that she loved and cared for him just as we would have. We will be using her again!”

About: Animals have always been a part of my life. They show us so much love. Who are we not to give it back in return. Since the passing of our long time dog (Roc,15) we’ve been watching our friends and family dogs while they’re out of town. In each case the owners return with their dogs a little hesitant about wanting to return home. LOL. I work from home and I have no plans of switching to another job that would require me to go into the office. Therefore, I have plenty of time to play with your big and little babies. I also like to take walks at minimum twice a day. This is a perfect time for your fur babies to stretch their legs. After a nice long walk I clean their paws to make sure they leave the yucky stuff outside. I have a designated area where they can sleep. However, I like to keep them close to me during the day while I’m working. I think it sets them up for a positive visit. They immediately become part of the family. I also have the flexibility to take them out throughout the day. There is a highly recommended veterinarian within a two minute driving distance and maybe a ten minute walk in the event of an emergency.
About: I have 1 dog and 2 cats of my own. My dog is my world and its my mission to give him the best life possible. I will treat your family as my own. I would be happy to do training while I visit your pets if you leave out commands and instructions for me. I appreciate communication and direction with your specific needs. :) I have most mornings open as I work 2nd shift. After my dog gets his training and walk for the AM.. I am free to do some visits for families! My pup gets 2 walks a day and off leash play in our backyard. He requires quite a bit of attention as he's got alot of energy to burn. We are training for service work so most of my time with him is playing games, bonding, and training. I am open to walking, playing, cuddling, training, and anything else you may need.. just ask and I will see if I'm your girl!
“Stephen and Amelie are the best! They take excellent care of our babies and our home when we’re away and make us feel completely comfortable when we need to travel without the pups. Our dogs love them too!”


“I’ve booked with Kelsey twice now within the last few months and I would book her services again in a heartbeat! She’s very thorough when she is taking care of my cats, and she provides an adorable Rover card every visit. She is fast to respond to messages, and 100% trustworthy with my cats! Kelsey is awesome! 😸😺”

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1. Search
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2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
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Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
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Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Silver Spring.
Rover makes it easy to find Silver Spring pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.







