House Sitting in Winthrop Harbor
Find a loving house sitter to watch over your pets and your home.

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winthrop Harbor house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Trina is such a lifesaver. We had a dog sitter lined up who had to bail on us about 12 hrs before we were supposed to leave on our first ever Disney vacation. She responded to my message immediately, was available on short notice and honestly spoiled the heck out of my dog! My dog is a senior citizen and takes 2-4 meds a day. She made sure he got all his meds, followed an intricate feeding schedule, and loved him as her own. She checked in with me daily to assure us he was doing well. She also helped feed our fish and turtle. What a lifesaver! We returned to happy animals and a very clean house. We will definitely be using Trina for all our vacations from here on out!”


About: I’ve worked hands-on with animals for over 12 years through shelters, rescue organizations, fostering, and TNR work. I’ve cared for everything from neonatal kittens to senior and special-needs animals, including medication administration and post-op recovery care. I’m calm, reliable, and experienced with animals that may be nervous, shy, energetic, or need extra patience. My goal is always to make pets feel safe, comfortable, and cared for while their owners are away. With my current work schedule, I’m available early mornings (5–6 AM) before work, again around noon, and throughout the evening. I make pets a top priority and can also provide late-evening check-ins to help pets settle in comfortably for the night. Based on your pet’s normal routine and comfort level, I can accommodate leash walks, supervised backyard time, or longer walks and exercise as needed.
“Faith was our first Rover sitter and will be our go to from here on out. She spent a week with our older dogs who require a lot of patience and care. She met their every need and then some. She goes above and beyond in every way. We received updates and pictures throughout her stay. She left the house clean and even left a wonderful letter and treats. Thank you, Faith, for all you did for our fluffy babies.”
“This was the first time using Rover. I could not be more pleased with the individual we picked when we chose Josh!!! He was readily available. He kept in great communication with us throughout the entire process from booking to his departure after watching our pups. He cleaned up and left house clean and tidy. Even kept the pups safe during a tornado warning. Cannot wait to book again with Josh!”


About: Hi! I’ve cared for pets for years through feeding, walking, playtime, and providing companionship. I understand that every pet has unique needs, and I strive to make them feel safe, loved, and comfortable while their owners are away. I currently work part-time, which allows me to maintain a flexible schedule and dedicate quality time to the pets in my care. I strive to provide reliable, attentive care through walks, playtime, feeding, and plenty of companionship. Your pet’s safety and comfort are my top priorities. I have a secure, fenced yard where dogs can play and exercise safely. I also have young children in the home who have been taught to be gentle and respectful around animals, helping create a loving, family-friendly environment for pets in my care.

About: I have experience working with all kinds of animals, as I grew up on a rescue farm. We rescued dogs of all ages and cats from multiple litters! I’m currently working full-time in a hospital, but I am looking for some extra work outside of it on the weekends and some weekdays. This is a great activity to decompress with animals and make extra money! I will ensure that I keep the clients home safe and secure when leaving. I will respect boundaries and ensure that I go and do my job, taking care and playing with your pets!
“Elizabeth was extremely professional, followed instruction, and took great care of my fur babies! I appreciated her consistent updates and I never worried during this sit so I will absolutely book again!”

“Sydney is awesome. She loves our dogs…and our dogs love her. She gave them all the attention and play time they could handle and were kept on a schedule that they were used to. She is awesome and our boys can’t wait to have her pup sit them again!”
“Sarah is amazing! From the first time I met her I knew my pets were in good hands. I was able to enjoy my time away knowing that my pup & cat would be happy and safe. She's already booked for our next vacation!!”

About: Hi, I’m Christine! I’ve been a devoted pet parent for over 30 years, and my love for animals is truly at the heart of everything I do. From playful pups to curious cats and every animal in between, I believe each furry (or feathery!) friend deserves love, care, and a whole lot of fun. I currently have an 8 year old Plott Hound who is recovering from her second TPLO surgery. I spend devoted time with her every day completing her physical therapy exercises and doing all I can to optimize her recovery and golden years ahead. She has been a major part of my life and we have had lots of adventures together! She has road-tripped with me to 21 different states and lived for 6 years in the high desert mountains of AZ. I pride myself on being patient, flexible, and truly attentive to every animal’s individual needs. Whether it’s a leisurely stroll or a playful adventure, I can’t wait to be a part of your pet’s journey! I am a certified wellness instructor and make my own client schedule- so- I have lots of flexibility and can work with most client’s individual needs. I am flexible and adaptive to each individual pet’s needs and environment. I love walking and am happy to give extra time to take in the sniffs- or enjoy a snuggle!
“This was the first time I've used Rover and found Sara. Communication was great from the get-go. As this was the first time I let someone else watch Iris (8 months old), rightfully so to be nervous and hesitant. Sara was very understanding and attentive as I went through what Iris needed, how her demeanor is, and all of the in-between. You could tell that Sara genuinely cares and enjoys caring for pets as a side gig. Sara was fantastic and we'll definitely book again.”


About: Hi! I’m a full-time stay-at-home animal lover with open availability, so your pet will always get my full attention 💕 I’ve grown up with animals, previously studied veterinary medicine, and volunteered at animal clinics, so I understand both the fun and the responsibility that comes with pet care. I have a busy, loving home with 3 kids, 2 dogs, and a bearded dragon, so your pet will fit right in! There’s always plenty of playtime, cuddles, and attention especially in the evenings when my kids love joining in 🐕✨ Whether I’m in your home or mine, I follow routines closely and treat every pet like family. You can count on your fur baby being safe, happy, and well cared for every step of the way 🥰 Pet care fits seamlessly into my daily life because I’m home full-time and already have a structured routine around caring for my own pets. From morning feedings and walks to playtime and evening wind-downs, taking care of animals is already a big part of my day not something extra I have to “fit in.” Adding your pet into my routine means they’ll naturally receive consistent attention, structure, and love as part of our everyday life. 🐾💕 I care for every pet based on their individual needs, routine, and personality. In my home, pets become part of the family right away they get plenty of attention, playtime, and a safe, clean environment. Since I’m home full-time, I’m able to keep a close eye on them, stick to feeding schedules, provide regular potty breaks, and make sure they’re comfortable and happy throughout the day. I also have a very active household with kids and pets, so there’s always engagement, exercise, and lots of love while still making sure your pet has space to relax if they need quiet time. When caring for pets in a client’s home, I make it a priority to follow their usual routine as closely as possible. I ask detailed questions about feeding, walks, behavior, and preferences so your pet feels safe and stress-free in their own space. I also keep the home tidy and provide updates so you feel at ease while you’re away. No matter where I’m caring for your pet, my goal is always the same: to make sure they feel safe, loved, and as comfortable as they would with you. 🐾💕
About: My family used to own 7 dogs when I was a preteen! 6 were chihuahuas and one was a pit bull, so I feel comfortable with any dog size. I would feed, walk, wash, and play with them. Now, I help my friends with their dogs whenever it’s needed. I know when they need space and when they want to be playful. I have a lots of energy, so I can ply with your pup for a long time! I’m a full-time student and work part-time for two days a week, but it only takes up in the morning. On any day of the week, I am available at any time after 4pm, and before 11am except on Tuesdays, Fridays, and Sundays. I’m always observing, partially because of admiration, but also watching out for any signs of discomfort. I can recognize when they need space, are uncomfortable, anxious, or threatened. I’m cautious when it comes to interactions while walking and will walk across the other side of the street from another dog for precaution.
About: I’m a retired professional firefighter. I’ve been caring for our pets, those of family and friends, and referrals for years. As a firefighter, I’m skilled and highly capable at handling any emergencies that could occur to your home in addition to providing the all important attention and care for your beloved furry family members. I retired from the fire service 5 years ago after a lengthy career and can attest to the statement that being a firefighter is the greatest job on earth. I’ve recently completed a major renovation of a unique custom home and have the time and desire to share my love of animals as well as my broad life experiences and skills in providing a special kind of care for your beloved furry friends while being able to handle any and all potential emergencies or inconveniences that could possibly arise. I believe that the best care that can be provided will always be best served in the environment that your pet calls their own home.
“Michelle cared for our two dogs at our home for the last 5 days/nights. We came home to happy dogs and a well cared for home. During our initial meet and greet, we immediately felt that we can trust Michelle with our dogs and our home and we were right. Michelle is a gem!!”

Over 20 pet parents in Winthrop Harbor have booked house sitting
Winthrop Harbor pet parents share their Rover experiences
Ariana was THE BEST!! I was so nervous leaving my three seniors for the first time, but on initial meet with Ariana I knew I didn’t have a thing to worry about. She kept me updated throughout and sent lots of pics. I had no expectations of any housesitting tasks/cleaning but she went above and beyond having my home tidy. Can’t say it enough, she’s the best !!!

Ariana did a terrific job caring for my two dogs while I was in the hospital for two days. She stayed over night with them, walked them, fed them and gave them their medications. Couldn't ask for better care for my pups--- a 14 year old ShihTzu and a 10 year old Poodle. I was relieved that my dogs were well taken care of. I highly recommend Ariana.

Ariana was AWESOME! She literally saved our weekend vacation after our original scheduled house/dog sitter no-showed on the morning we were supposed to leave. Ariana was able to come over a few hours after confirming, she asked appropriate questions and was attentive. I felt awful because we have two geriatric dogs. It turned out not to be as smooth of a weekend for Ariana, as we thought it would be. What has always presented to us as food eccentricities and separation anxiety in our 15 yr old Shih Tzu, may be end- of- life symptoms, as he refused to eat, drink, and had explosive diarrhea in the middle of the night and was spitting up on the last night we were away. Ariana handled everything in the most professional and respectful manner she could. She called me at 3:30 am (which I appreciate more than anything) and advised me Mushu had explosive diarrhea, he was spitting up, and wasn't eating, and asked what I wanted her to do. I appreciated this so much because I know my dog better than anyone, and have dealt with him "being Mushu" for 15 years, and I knew we would be leaving the following morning to come home. We got home yesterday. I called his vet and we made a plan to monitor him overnight to see if he returned to previous perkiness and started drinking/eating. Again, Ariana was very professional and used great instincts to overcome a difficult weekend.

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Winthrop Harbor is $50
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Sitters in Winthrop Harbor average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winthrop Harbor on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 2,530 house sitters in Winthrop Harbor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Winthrop Harbor house sitters respond in under an hour.
House sitters in Winthrop Harbor have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winthrop Harbor.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winthrop Harbor house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.




