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

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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.
“We had an absolutely amazing experience with Faith! She was incredibly attentive to detail, kept our home spotless, and took such thoughtful care of our pup. You can tell she truly loves animals. She is patient, engaging, and our dog looked happy and relaxed in every update. Her communication was excellent, we received regular photos and updates, which gave us total peace of mind while we were away. She followed all instructions perfectly and made sure routines stayed consistent. If you're looking for a reliable, trustworthy, detail-oriented, playful, and communicative house sitter or pet sitter, I can’t recommend Faith enough. We will absolutely be booking with her 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!”
“Joshua was 100% exceptional from the 1st communication to the end of his stay with our German Shepherd, Kai. He came over twice before the stay to get acquainted with Kai, the house, the neighborhood etc. He communicated daily with pictures of Kai and letting us know how she was, that she was eating and exercising. He stayed in our home from Friday-Sunday. All was clean and in order when we arrived home. We highly recommend him!”


About: Worked at a few veterinary hospitals when I was younger. Pet sitting fits my busy mom life and I adore it. Super comfortable with any kind of animal and able to administer medication (even i.v) properly. Also able to recognize any signs of illness or injury in pets while you are out. This is all I do. Giving these pets all of my attention and professionalism is part of my everyday routine. Knowing they are with someone like me will make your day easy. I’ll care for your pets in your own home. This way they are very comfortable in their own environment. Safety and affection are my priorities while they are in my care. Whether it’s a potty break or a walk or even just a check in, they’ll know they are cared for.
“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!”

“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!!”

“Isabella did a great job caring for my two boys while I was away for a few days. She checked in daily with updates and adorable pictures - it was clear my babies took to her immediately which gave me such peace of mind. She was kind enough to water my balcony full of plants for me and kept the house super tidy, I could barely tell she was here it was so nice. Thank you Isabella for being so amazing!”

“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!”

“Diamond was a lifesaver! She was our house sitter for our dog and two cats while we were away for over a week. She arrived early, followed all special requests for the pets’ meals and activities, kept the house clean, and sent so many great pictures to keep us in the loop! Really put our mind at ease which made it easy to enjoy our trip 😊”

“Brittany took care of my 2 senior dogs while we were away for 3 days. One of our dogs requires meds 3 times a day, and she is an over reactive dog. Brittany handled a situation with another dog that was off leash very effectively! My dog does not like other dogs, and she picked up my dog to avoid a potentially dangerous situation. Overall she took very good care of their needs, even walking them a couple times a day when she could have just let them in the fenced yard. I would definitely recommend Brittany to watch over your pets and give them the best of care.”

“I couldn’t be more grateful for the care Tanya provided our two dogs! They are two rescues who can be a bit challenging at times, but she was so patient, understanding, and handled them with so much love. It gave me a real peace of mind knowing they were in such capable hands. Highly recommend!”

About: I have had pets all my life and love pets of all kinds! A dog owner forever, I am a recent cat lover and am happy to help your furry cats as well. I have experience in quick visits and long-term care for dogs and cats! I work on a school schedule, so I am available all evenings and weekends! I can always do morning care as well prior to the start of my work day. I have a friendly dog and cat who get along with all animals. I am able to crate your dog or provide a secluded space if needed! A private dog park is on my property.
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: 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!

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. 🐾💕
“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: I’ve taken care of families pets since I was 14 years old. As well, I have raised 3 puppies and just finished training my friends new 8 week year old puppy that’s growing up to be a great boy! I care for dogs and all pets and their lifestyle and overall health emotionally and physically to make sure they get all their needs. I am currently a college senior student working a front desk job at a salon and I’m looking forward to taking care of some pups. 😊 I am currently home from a college winter break yet I reside in Chicago. I am familiar with the area and have a huge love for animals and their care. I am currently working part time as a front desk receptionist and a salon in downtown Chicago and I am looking for something else to do that I enjoy on my free time. I want to prioritize a pets needs and wants, taking instructions by a pets owner comes first since they know their pet best! Taking insight on the pets breed and making sure you keep them on a consistent schedule and maintaining it is super important for a dogs happiness. Keeping them entertained and safe is key! I would make sure I treat all pets like they are my own.
Over 14 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.

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 $55
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 $55 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 794 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, 85% of Winthrop Harbor house sitters respond in under an hour.
House sitters in Winthrop Harbor have an average of 17 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.



