House Sitting in Winfield

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Top rated Winfield house sitters

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: Sabrina A.
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Sabrina A.
from
$100
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
20 years of experience
Merrillville, IN, 46307

Sabrina was amazing with my pups. Sabrina was very professional. Sabrina was quick to respond to messages and work with us on such short notice. If your looking for the perfect sitter, look no further than Sabrina.

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Tamara P.
Sitter Profile Image: Alexandria Q.
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Alexandria Q.
from
$70
per night
4.9 out of 5 stars
49 reviews
12 repeat clients
5 years of experience
Crown Point, IN, 46307

So glad I found Alexandria to take care of my cat when I was gone. She is very dependable and was loving toward Bruno. You would not be disappointed to book with her.

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Rick G.
Sitter Profile Image: Eli W.
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Eli W.
Star Sitter
from
$55
per night
5.0 out of 5 stars
39 reviews
11 repeat clients
10 years of experience
Merrillville, IN, 46410

Eli did a fantastic job house sitting with our dog and senior cat this weekend. He was so good attending to all their needs, and constantly kept us updated with photos. We'll definitely be booking in the future! Thanks Eli

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Louise B.
Sitter Profile Image: Sydney H.
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Sydney H.
from
$55
per night
5.0 out of 5 stars
5 reviews
6 years of experience
Saint John, IN, 46373

About: Hi! I’m Sydney, and I have over 6 years of hands-on experience caring for dogs of all sizes, ages, and personalities. I previously worked as a kennel attendant at a local animal shelter, where I was responsible for feeding, walking, cleaning, monitoring behavior, and ensuring the overall health and safety of the dogs in my care. I am experienced with senior and special needs dogs, including administering oral medications and carefully following detailed care instructions. I understand how important patience, consistency, and attention to detail are, especially for pets who need extra support. I’ve cared for puppies, high-energy dogs, anxious dogs, and pets with strict routines. My goal is always to keep your pet comfortable, safe, and on their normal schedule while you’re away. I treat every dog like my own and provide regular updates so you can feel confident and at ease! Pet care is my full-time focus, which allows me to dedicate consistent time and attention to every pet I care for. I structure my daily routine around feedings, walks, playtime, and any special care needs to ensure each pet receives reliable and attentive care. Because this is my primary job, I am able to be flexible, maintain consistent routines, and provide dependable updates while you’re away. Your pet’s safety, comfort, and well-being are always my top priorities. I provide care exclusively in my clients’ homes so pets can remain in their familiar environment and routine. I understand that staying in their own space reduces stress and helps them feel safe and secure while you’re away. I carefully follow all care instructions, including feeding schedules, walks, medication, and any household rules. I am respectful of your home and maintain a clean, secure environment at all times. I ensure doors, gates, and crates are properly secured and prioritize your pet’s safety during walks and outdoor time. Clear communication is very important to me, and I provide regular updates and photos so you can feel confident and at ease while you’re away.

Sitter Profile Image: Karina R.
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Karina R.
from
$65
per night
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Hobart, IN, 46342

I’m so glad I tried looking for another sitter and found Karina! She did a fantastic job! She truly cared for Zoey and made time to know her, and eventually they became buddies! Zoey has a separation anxiety and could be difficult to handle (she won’t leave the house even to go potty). But Karina took effort & was so patient with Zoey and made sure she got to potty for the day. The house was the same as how we left it. I definitely will book Karina again even for drop ins! Thank you so much, Karina! We appreciate you so much!

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Jennifer P.
Sitter Profile Image: Hannah B.
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Hannah B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
98 reviews
37 repeat clients
15 years of experience
Demotte, IN, 46310

Hannah is seriously the best! One of our dogs had an unexpected medical issue that came up (not requiring a vet) hours before we were supposed to leave town and Hannah was comfortable keeping a close eye on him and keeping us updated throughout the weekend. She’s our go-to sitter!

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Erika T.
Sitter Profile Image: Holly S.
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Holly S.
from
$30
per night
15 years of experience
Valparaiso, IN, 46383

About: I've taken care of family pets (cats and dogs) for 15+ years now, and on my own I a have two cats. My schedule is flexible, though my apartment does not allow for dogs and I prefer to pets sit at the pet's home, where they are most comfortable and familiar. I do not have experience caring for pets with serious medical conditions, but I have given dogs their medication on previous jobs. I am currently only available on weekends, though as I transition out of teaching my schedule will open up. I am available for any emergencies over the holidays. My apartment does not allow for dogs, and would prefer not to test how my cats would respond to other animals as it has been just them in my apartment for a few years now. I also believe that it's best to sit for apet in their own home where I am the only thing they have to adjust to. I am fastidious about following owner directions. My cats are fairly low-maintenance, but I also have experience with high-energy dogs like boxers, and pet size does not matter.

Sitter Profile Image: Anna W.
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Anna W.
from
$35
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
3 years of experience
Merrillville, IN, 46410

Anna was absolutely wonderful, and we are so thankful for her! We were a little nervous, as we haven't had to leave our dog with someone other than my parents before, and we were going overseas for a trip with my parents. But Anna was delightful, good at communicating with us, and seemed to care so well for our dog!

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Rachel Elizabeth S.
Sitter Profile Image: Samantha M.
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Samantha M.
from
$30
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Gary, IN, 46404

Samantha was amazing! She was very professional and my dogs immediately took to her. I have never had someone watch my dogs at our house and I was very nervous but she put my mind at ease and I will definitely be using her for future bookings!

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Brittany H.
Sitter Profile Image: Pablo B.
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Pablo B.
from
$42
per night
5.0 out of 5 stars
6 reviews
12 years of experience
Hobart, IN, 46342

Pablo was wonderful in taking care of our two very sweet, but fairly high-maintenance dogs over a five-day weekend. He was caring, organized, and very responsive. We came home to happy dogs and a neat house. Thank you so much.

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Aaron S.
Sitter Profile Image: Kimberly V.
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Kimberly V.
Star Sitter
from
$123
per night
4.9 out of 5 stars
51 reviews
9 repeat clients
40 years of experience
Valparaiso, IN, 46383

Kimberly was so attentive to all of our dogs needs! She made sure they were safe, happy, & healthy. We have more high maintenance dogs and she was the perfect sitter for them. In addition to making sure our dogs were perfectly taken care of, she went above and beyond with house sitting too! My house is going to be sad I’m back because Kimberly took such great care of the house and garden! 🥰

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Kortney S.
Sitter Profile Image: Juana P.
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Juana P.
from
$45
per night
5.0 out of 5 stars
5 reviews
1 repeat client
16 years of experience
Crown Point, IN, 46307

About: I’m the person people rely on to baby sit. I have the love and passion to care and attend to dogs as my own. I have experience as a medical assistant which allows me to make rational decisions to maintain a safe environment for your beloved pet. Self taught cpr and other emergency procedures. I’m currently a home stay dog mom and would love to give my love and attention to other dogs and cats. I’m available and flexible to work with the parent. I have a friendly dog that loves company and would help your dog settle in for a fun baby sitting date. Safe uncluttered clean environment pet friendly. Walking paths available for the dog to enjoy for a potty break. Back yard available, spacious two floor.

Sitter Profile Image: Racheal J.
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Racheal J.
from
$50
per night
3.0 out of 5 stars
3 reviews
1 repeat client
25 years of experience
Lake Station, IN, 46405

Racheal is the best dog sitter! We love her!

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Lisa E.
Sitter Profile Image: David R.
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David R.
from
$50
per night
4.9 out of 5 stars
40 reviews
14 repeat clients
18 years of experience
Hammond, IN, 46324

David did a wonderful job taking care of our cat and dog. He sent pictures daily, and was attentive to our cat who his shy around new people. Would definietly recommend, and we have already rebooked !

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Sarah K.
Sitter Profile Image: Ken W.
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Ken W.
from
$80
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
40 years of experience
Crown Point, IN, 46307

Ken was great. My dogs fell in love with him. they ask about him every day. Ken is very pragmatic, has a list he goes over. I will only use him moving forward. This is is full time gig. Thus it isn't a hobby, or a side job. He takes this very seriously. It showed!!!!!!!!!!!!!

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Eric T.
Sitter Profile Image: Jacob R.
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Jacob R.
from
$70
per night
6 years of experience
Crown point, IN, 46307

About: As a husband and wife team, we offer a level of attention and dedication that ensures your furry friend feels safe, comfortable, and loved. What sets us apart is that one of us is always home with your pup, providing constant care and companionship. Whether it's a boarding stay or a daily walk, each pet receives attentive, tailored care to meet their specific needs. If I'm not out walking or doing drop-in visits, I'm right here, helping support Jacob and ensuring every pet gets the attention they deserve. We're experienced in administering oral or insulin medication, following special diets, and adhering to specific let-out instructions, ensuring their comfort, safety, and your peace of mind. With us, you're not just hiring a pet sitter; you're entrusting your pet to a caring team dedicated to their happiness and well-being. Pet care fits seamlessly into our daily routine. We offer flexible boarding and dog walking/drop-ins daily from 8 AM to 8 PM, ensuring your pet always receives consistent, professional care. We prioritize safety and comfort for pets in our care, whether in my home or theirs. Keeping boarding limited! My home offers a huge fenced backyard with monitored outdoor fun! Can cage if necessary for bedtime. In clients homes, we follow their routines closely. Either way, we focus on creating a nurturing environment with personalized attention.

Sitter Profile Image: Lindsey H.
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Lindsey H.
from
$40
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
30 years of experience
Lowell, IN, 46356

Lindsey was great. My dog had a great time w lots of attention & walks. She was great w my Doberman who is a bit leery of new people & has lots of energy. I’ll definitely be using her again!

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Kelly C.
Sitter Profile Image: Rob S.
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Rob S.
from
$47
per night
4.9 out of 5 stars
39 reviews
9 repeat clients
8 years of experience
Hammond, IN, 46327

Hi Rob, is a good person and a lifesaver. He came over and Housesat for me in an emergency with only 3hrs notice when I had a last minute cancellation. I would recommend him again to watch my pets anytime

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Tyrone L.
Sitter Profile Image: Patti F.
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Patti F.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
40 years of experience
Valparaiso, IN, 46383

About: What can I say other than l love dogs. Actually I love all animals but especially dogs. I have had or been around dogs my whole life. We currently have a 5 year old Black Labrador named Veva Marie. In October of 2018 we had to have our 16 year old Lhasa apso Sadie put to sleep. One of the hardest days of my life by far. Dogs have always been more than just a pet to me, they are definitely family.I want you to feel confident knowing i will care and love your pet as if it were my own while you are away or at work. I also have experience in caring for cats and would love to help in caring for them also if you need me to. I look forward to meeting you and your fur baby and helping you with taking care of them. I am currently self employed part time, therefore I am extremely flexible with whatever you need in caring for your pets and look forward to hearing from you. I live on 2 acres in Wanatah, Indiana. My preference is to walk in neighborhoods and parks that are local for your pets or whatever you prefer! I currently work a full time day job but am looking to help people with their fur babies on the side. Luv 4 legged animals❤️ I am available for walks, drop in visits, and also house sitting if needed. Reach out and let me know how I can help you!

Sitter Profile Image: Sydney T.
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Sydney T.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
16 years of experience
Crown Point, IN, 46307

Sydney was excellent! She housesat and watched our pups for a few days on a last minute trip. She took great care of both, sent regular updates, and made sure all was tidy before we returned. She will be out first call when we need a sitter again.

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Shawn W.
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Winfield pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

AMAZING every sit! I never have to worry about anything when Margaret is sitting and my dogs adore her! Couldn't reccomend her more! House is always so clean too! Thank you!

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amy c.
House Sitting
5.0 out of 5 stars

Dogs were happy with Veronica watching them for the first time. Home was left neat and clean. Definitely recommend her.

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Marilyn K.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 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. 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 Winfield 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 Winfield 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 Winfield on Rover as of Mar 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.

If you’re searching for a Winfield house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Mar 2026, there are 315 house sitters in Winfield. 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, 87% of Winfield house sitters respond in under an hour.

House sitters in Winfield have an average of 14 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 Winfield.

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. Winfield 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.