House Sitting Winthrop Harbor

Find a loving house sitter to watch over your pets and your home.

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Over 18
pet parents in Winthrop Harbor have booked house sitting

Winthrop Harbor, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Joshua C.
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Joshua C.
from
$50
per night
4.8 out of 5 stars
19 reviews
9 repeat clients
7 years of experience
Kenosha, WI, 53142

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!

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Julie F.
Sitter Profile Image: Faith Q.
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Faith Q.
Star Sitter
from
$50
per night
4.9 out of 5 stars
54 reviews
38 repeat clients
20 years of experience
Gurnee, IL, 60031

Highly recommend Faith! She took incredible care of our dog & cat while we were away! She sent regular photos and updates and we came home to a clean house and happy pets!!!

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Terri B.
Sitter Profile Image: Alexis K.
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Alexis K.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
3 years of experience
Lindenhurst, IL, 60046

Alexis was phenomenal watching Isabelle. She has a given talent for dog sitting!! Isabelle enjoyed her company.

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Larry T.
Sitter Profile Image: Victoria-Anna K.
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Victoria-Anna K.
from
$30
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
4 years of experience
Kenosha, WI, 53944

About: I’ve had pets most of my life… I’ve had dogs, cats, bunnies and guinea pigs. I’ve house sat which included farm animals. I am patient and willing to give all my love to any animal even if they aren’t mine. I am a student so I would come between classes, before classes, and after to take care of any pets. I do not have a full time job. I want to work with whatever you have at your house. I will make sure that all of your rules are followed, and that your fur babies are well taken getting care of.

Sitter Profile Image: Trina R.
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Trina R.
from
$70
per night
5.0 out of 5 stars
10 reviews
1 repeat client
17 years of experience
Beach Park, IL, 60099

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!

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Lana M.
Sitter Profile Image: Michelle Z.
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Michelle Z.
Star Sitter
from
$70
per night
5.0 out of 5 stars
47 reviews
15 repeat clients
3 years of experience
Sturtevant, WI, 53177

Michelle was great with our 2 dogs. One dog is very shy, and nervous. Michelle gave her the space & time, to be comfortable with her. She took great care of the dogs, as well as, our home. She was great at communicating, sending updates, and pictures. We'll definitely be using her again.

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Jean B.
Sitter Profile Image: Elizabeth P.
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Elizabeth P.
Star Sitter
from
$70
per night
5.0 out of 5 stars
13 reviews
3 repeat clients
1 year of experience
Waukegan, IL, 60087

Elizabeth did a great job watching my dogs while I was away. She handled two pretty demanding dogs with ease and communicated proactively throughout to ensure all my concerns were addressed. I can tell my dogs had a great time with her and would highly recommend her to anyone.

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Tom B.
Sitter Profile Image: Tanya K.
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Tanya K.
from
$75
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
15 years of experience
Gurnee, IL, 60031

Tanya was the best. She stayed at our house watched our pets and house for a week. We have a dog with severe mobility issues, an 18 year old cat and 2 younger cats — all with unique needs and 2 that require meds. She was so wonderful with our fur family and home. HIGHLY recommend her services to anyone who cares about their pets being well taken care of and loved. She also dealt with packages and cleaning people and day to day household responsibilities with ease. She sent us pictures and kept us updated daily. Thank you!!!

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Kendra S.
Sitter Profile Image: Amanda M.
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Amanda M.
from
$28
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Kenosha, WI, 53140

Amanda was great. She followed instructions and sent lots of pictures. She communicated well. Dogs were treated with care and kindness. Great sitter

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Debbie G.
Sitter Profile Image: Daniel L.
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Daniel L.
from
$38
per night
7 years of experience
Winthrop harbor, IL, 60096

About: Always had 4+ animals in my household (fish as well!) and always enjoyed taking care of them and going on walks/runs and playing with them. I’m pretty flexible when it comes to scheduling and I’m happy to work around your needs and your pet’s routine. Whether you need someone for a quick drop in, a few days, or even a longer-term stay, I’ll be happy to help! I know how important it is to have someone you trust with your pets, and I’ll treat them like they’re my own while you’re away. 🐶🐾 I’ll do my best to make sure your pets are well taken care of and comfortable in your home. Whether that means playing with them, taking them for walks, feeding them, or even giving them a bath. I’ll treat your pets with the same care and attention I’d want for my own.

Sitter Profile Image: Leah J.
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Leah J.
Star Sitter
from
$40
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
6 years of experience
Kenosha, WI, 53140

Leah did a great job watching Harley (soft coated wheaten terrier) while we went on a short 4 day trip. Kept us up to date on how he was doing and made sure he had his walks and breaks.

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Deena N.
Sitter Profile Image: Karen C.
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Karen C.
from
$28
per night
4.0 out of 5 stars
2 reviews
2 repeat clients
2 years of experience
Pleasant Prairie, WI, 53158

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.

Sitter Profile Image: Isabella T.
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Isabella T.
from
$75
per night
5.0 out of 5 stars
23 reviews
12 repeat clients
18 years of experience
Beach Park, IL, 60087

We never used a dog sitter before in our home. Isabella was amazing and took such great care of our dogs. Highly recommend her and we will use her all the time now.

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Ed B.
Sitter Profile Image: Robert P.
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Robert P.
from
$25
per night
14 years of experience
Winthrop Harbor, IL, 60096

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.

Sitter Profile Image: Jahaira C.
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Jahaira C.
from
$30
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
4 years of experience
Kenosha, WI, 53143

About: I have taken care of cats, dogs, guinea pigs, chinchillas throughout several years. I have a passion for care taking all kinds of animals from all ages. I am very patient and have experience with things such as administering medications. I also am very attentive to details and flexible with any kinds of needs your pet may have! I recently completed graduate school as a PA and recently moved to the Kenosha area. I currently have plenty of time to care for your pets. I am generally free and available most days of the week and I can be flexible! I live in a safe friendly neighborhood with plenty of areas to walk dogs and play outside. I have no pets at home currently, I do have a small yard.

Sitter Profile Image: Cynthia G.
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Cynthia G.
from
$35
per night
5.0 out of 5 stars
1 review
1 year of experience
Pleasant Prairie, WI, 53158

About: Whether your pup enjoys long walks, playtime, belly rubs, or simply relaxing with someone nearby, I’ll make sure they feel comfortable, safe, and loved while you’re away. My goal is to provide a calm, loving environment where your pet receives plenty of attention, affection, and exercise. I am retired so have plenty of time to play with and walk your fur babies as much as needed. I can play with your dog in our fenced in yard or walk them on the Bike Trail, which is just a block away from our home. I’ll tailor my care to each dog’s individual personality and routine. I know how important consistency is, so I’ll follow your feeding schedule, medication instructions, exercise needs, and any special requests. I like to text or email regular photo updates and messages so you can relax knowing they’re having a great time, communication is just as important as great pet care.

Sitter Profile Image: Alissa K.
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Alissa K.
from
$40
per night
10 years of experience
Kenosha, WI, 53142

About: I've been dog-sitting my friends' & neighbors' dogs for years now. Everything from Shih Tzus to Labs to Collies and Pit Bulls, I do well with all types of dogs! I love taking dogs for walks and playing fetch! (Also, I love cats! (I'm a Cat Mom of 4)). I'm currently working part-time, so I have plenty of time to take care of your pet(s)! My weekly availability varies, but I keep my calendar up-to-date. I respond promptly to requests, so feel free to reach out and ask! I am always respectful of my clients' homes & make sure I take the dogs out frequently to use the bathroom & for walks/play, that litter boxes are cleaned, & that there is always fresh water/food given.

Sitter Profile Image: Sara J.
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Sara J.
from
$85
per night
5.0 out of 5 stars
30 reviews
4 repeat clients
13 years of experience
Pleasant Prairie, WI, 53158

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.

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Beric W.
Sitter Profile Image: Ethany I.
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Ethany I.
from
$55
per night
4.0 out of 5 stars
4 reviews
2 repeat clients
13 years of experience
Winthrop Harbor, IL, 60096

Ethany did a great job! She was very attentive to our pets and kept me informed. Thank you!!

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Corey S.
Sitter Profile Image: Savannah N.
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Savannah N.
from
$30
per night
2 years of experience
Waukegan, IL, 60085

About: My whole life I've grown up with dogs and other animals. I truly care about pets and their well being. I'm pursuing a degree in animal behavior and welfare. I also have watched family pets growing up. I'm currently without a job so I'm available to watch your animal(s) full-time, part-time, or over night if need be. I do live an apartment, but I have plenty of walking space outside, cat toys and trees for anyone with cats. I'm willing to work on a schedule if you need strict walking times or for feeding. I'm willing to train for free using reward-based training techniques and I'm willing to bathe for free if you'd like.

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The median cost per night for house sitting in Winthrop Harbor is $55

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Winthrop Harbor

Select a filter and find qualifying sitters offering house sitting.

Sitters in Winthrop Harbor average 4
repeat house sitting clients

FAQs for House Sitting - Winthrop Harbor

Frequently asked questions about Rover

The average cost for House Sitting in Winthrop Harbor on Rover is $59.97 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of September 2026, there are 2,480 sitters on Rover offering House Sitting across Winthrop Harbor. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winthrop Harbor walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Winthrop Harbor maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winthrop Harbor choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Winthrop Harbor. On Rover:

  • 93% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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