House Sitting Winfield

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

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Over 40
pet parents in Winfield have booked house sitting

Winfield, 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: Gillian C.
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Gillian C.
from
$38
per night
5.0 out of 5 stars
8 reviews
4 repeat clients
10 years of experience
Schererville, IN, 46375

Gillian did great caring for my dog and 4 cats over night. They were all very comfortable with her and allowed for me to enjoy my night away from home.

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Damon S.
Sitter Profile Image: Madison B.
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Madison B.
from
$50
per night
5.0 out of 5 stars
1 review
1 repeat client
20 years of experience
St. John, IN, 46373

About: I’ve taken care of dogs and cats since I was a kid. I have house sat for at least three different people and took care of their pets! I’ve worked with senior dogs and puppies. I also have a part time job at a pet store so I have a decent amount of knowledge on pets and am more than happy to get things from the store for you! I have also administered medicine to a dog with health issues so I am comfortable administering medicine. I work part-time at a pet store! But I have time in between these things to drop in on pets and walk them, play with them, and even feed them. I’m happy to do whatever needs to be done’ My cat is older so she doesn’t play much anymore, but I’ve played with lots of kitties before. I’ve also played with dogs, big and small. My old home had a fenced in yard that I used to play with the dogs in. I no longer have that, but I love taking my own dog on long walks to burn off some of that energy!

Sitter Profile Image: April Y.
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April Y.
Star Sitter
from
$85
per night
5.0 out of 5 stars
57 reviews
16 repeat clients
15 years of experience
Merrillville, IN, 46410

April watched our gaggle of pups when we had to unexpectedly go out of town. She did an amazing job with them, was responsive, and I felt at ease knowing she had a handle on our crew. We have a puppy and an older guy needing medical care and she handled both so well. I would definitely recommend April!

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Allison S.
Sitter Profile Image: Brent D.
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Brent D.
from
$28
per night
5.0 out of 5 stars
1 review
1 repeat client
2 years of experience
Hobart, IN, 46342

About: Grew up having a dog (or 2 at times…as well as bunnies…and some other reptiles!). I currently live in an accommodation where I am not able to have a pet and I have become to miss animals more and more! There is no such thing as a bad animal, only a poorly trained one, and I treat them all with love and care. I’m available every Sunday, Monday, and Tuesday all day (and night)! My schedule can be as free as needed on those days and I am open to spending lots of time with your pets to make sure they get the best care possible! I am very careful and thoughtful around pets and other people’s property. I will treat your belongings and animals with the utmost respect and care.

Sitter Profile Image: Alexandria Q.
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Alexandria Q.
from
$80
per night
4.9 out of 5 stars
50 reviews
12 repeat clients
5 years of experience
Crown Point, IN, 46307

Alex was great! First time having a house sitter stay with our pup and everything went smoothly! Alex sent lots of updates and photos while we were gone. Will definitely use her for our next trip.

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Stephanie M.
Sitter Profile Image: Hannah B.
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Hannah B.
Star Sitter
from
$85
per night
5.0 out of 5 stars
109 reviews
40 repeat clients
15 years of experience
Demotte, IN, 46310

Hannah was great. She was so kind, a good communicator and helped my pups feel safe. She left the house in great order-- just as we left it. This was a last minute booking and she was so agreeable. I am very pleased with her services!

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Melanie J.
Sitter Profile Image: David R.
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David R.
from
$50
per night
5.0 out of 5 stars
47 reviews
15 repeat clients
18 years of experience
Highland, IN, 46322

We truly appreciate David’s care of our pup and home while we were away. He followed instructions to a T and was proactive with communication. We loved the routine updates and pictures, especially seeing that Bailey was getting his walks when weather allowed.

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Kathyjo S.
Sitter Profile Image: Gabriela L.
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Gabriela L.
Star Sitter
from
$30
per night
4.9 out of 5 stars
34 reviews
8 repeat clients
1 year of experience
Highland, IN, 46322

About: I have been around dogs and cats since I was a kid. Growing up I had an adorable pit bull that I would feed, walk, and bathe regularly. My family and friends also had cats that I would occasionally watch and feed as well. Recently I have excelled with sticking to strict dietary restrictions for a senior dog I sat to also helping leash train and walk my siblings 6 month old dog. I'm a full time college student and have a part time job. Luckily between my class schedule and work schedule I have more than enough flexibility to provide the service you and your pet need. I have personal dog walking experience and can provide a comfortable walking environment for your pet. I also have experience with rowdy dogs and can safely handle playtime.

Sitter Profile Image: Timothy G.
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Timothy G.
from
$30
per night
5.0 out of 5 stars
3 reviews
1 repeat client
3 years of experience
Valparaiso, IN, 46385

About: I’ve worked at a dog hotel, and I’ve pet sat for both cats and dogs. I’ve never met a dog that didn’t like me, and I’ve never met a cat that didn’t tolerate me. I’m a student pilot, so some days I have about 2 and a half hours where I won’t be available. Otherwise I have a very flexible schedule and can spend all day or any time caring for your pet. I don’t have any pets of my own, but I’m good at making anyone’s pets friendly with me. I’ve done daily check-ins and up to two weeks staying at someone’s house to keep their dog active and happy.

Sitter Profile Image: Gia C.
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Gia C.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
6 years of experience
Valparaiso, IN, 46385

Gia was an excellent house sitter and pet sitter. I have two older cats, and was a little nervous about leaving them for two weeks. But when I returned, my house was clean, my cats were happy and well fed, and my mail was stacked on the kitchen table. Gia contacted me several times during my vacation, and sent photographs and video of the cats at home. I highly recommend her!

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Elaine P.
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: Brenda D. B.
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Brenda D. B.
from
$34
per night
4.9 out of 5 stars
22 reviews
4 repeat clients
5 years of experience
Hobart, IN, 46342

Brenda stayed at our place and took great care of our cat while we were away. She communicated daily and provided updates and photos and I could tell she was sweet with him and he warmed up to her despite his shy nature. I could tell Brenda has a lot of experience with pets, and she was very diligent with our home and thoughtful in her communication.

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Monika H.
Sitter Profile Image: Emaretta H.
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Emaretta H.
from
$100
per night
5 years of experience
Crown Point, IN, 46307

About: I’m an adult who is passionate about providing dependable, loving care for animals of all ages while their owners are away. I’m especially comfortable with senior pets who may need extra patience, attention, slower walks, medication routines, or simply more companionship. I respect each pet’s individual personality and routine and want owners to feel completely comfortable knowing their animals and home are in caring, responsible hands. My pet-care schedule is flexible and built around my clients’ needs. I intentionally plan my week around bookings, allowing me to accommodate daytime visits, walks, overnight stays, weekends, and extended care. I enjoy making pet care a priority rather than trying to squeeze it into a busy schedule. I provide care in your pet’s own home, where they can stay comfortable with their familiar surroundings and routine. I carefully follow feeding, walking, medication, and household instructions and give each pet the individual attention they need. I’m respectful of both your pets and your home, with communication and updates while you’re away.

Sitter Profile Image: Briana M.
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Briana M.
from
$70
per night
5 years of experience
Crown Point, IN, 46307

About: I’ve been a dedicated dog mom for 6 years and have experience caring for dogs through all kinds of situations — from energetic puppy stages to recovery days that require extra patience, comfort, and attention. I understand how important trust is when leaving your pet with someone, and I’ll care for them like family. Pet care is already a big part of my daily life. My days naturally revolve around walks, playtime, feeding schedules, outdoor time, and making sure pets feel safe, comfortable, and loved. I genuinely enjoy spending time with animals, whether that’s going on walks, relaxing together, or giving extra attention when they need comfort and patience. When caring for pets in a client’s home, I do my best to keep their routine as normal and stress-free as possible. I follow feeding schedules, potty breaks, walks, medication instructions if needed, and make sure pets get plenty of attention, playtime, and comfort. I also respect my clients’ homes by keeping things clean, secure, and providing updates so they can feel at ease while they’re away.

Sitter Profile Image: Alexia W.
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Alexia W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
22 reviews
3 repeat clients
6 years of experience
Valparaiso, IN, 46383

Alexia was great with our dogs. She took great care of our dogs, the house and even checked on our chickens for us. She communicated with updates, pictures and even stayed a bit longer when our flight was delayed. Definitely recommend.

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Emily S.
Sitter Profile Image: Ashley B.
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Ashley B.
from
$40
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Schererville, IN, 46375

About: I have always cared for animals my whole life. I am a stay at home mama to a 1 year old that is trying to get out and see new animals! my schedule is very flexible. I am open majority of the day, the only time that I am not available is early morning 6 AM-8 AM. I am patient and willing to follow all requests asked. I have a very high maintenance dog- so I get all concerns! I just want to make clients happy!

Sitter Profile Image: Allie B.
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Allie B.
from
$45
per night
5.0 out of 5 stars
9 reviews
20 years of experience
Gary, IN, 46407

Allie was very attentive and communicated every time she stopped by the house to let the dogs out. She sent pictures every time as well as a couple videos. The dogs loved her company and they were well cared for!

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Alyssa G.
Sitter Profile Image: Shawn W.
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Shawn W.
from
$50
per night
4.6 out of 5 stars
17 reviews
3 repeat clients
7 years of experience
Fair Oaks, IN, 47943

Shawn did an awesome job of taking care of Oliver for 5 days, the longest we have ever left him. We came home to a happy boy and a tidy house! We are very grateful to Shawn for the peace of mind we had knowing Oliver was well taken care of during our absence.

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Barbara B.
Sitter Profile Image: Rebecca P.
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Rebecca P.
from
$40
per night
8 years of experience
Valparaiso, IN, 46385

About: Hello, I'm Rebecca. I'm 28 years old. I've always been an animal lover. I live with my parents who have had multiple dogs over the course of my lifetime. Being the only child still living with them, I've become their dog sitter anytime they leave for a trip, etc. I began experiencing disabling health issues right out of high school and resorted to dog sitting as a way to make money as I was not able to hold a "real" job. I grew to love it. I'm healthier now and looking to find more opportunities outside of friends, family, and neighbors. I would love to broaden my horizons and care for fur babies full time. I'm currently unemployed and have a very open schedule. I have experience caring for puppies, elderly dogs, and anything in between. I know how to administer medication and clean up accidents due to my past elderly dogs having health complications. I also have experience caring for rabbits and cats. After the passing of my 9 year old rabbit in June 2025, I felt like a piece of me was missing. Only a couple months later, I started dog walking for a woman in my neighborhood daily and it helped me through the grief of losing my bunny. That's what caused my desire to dog sit/walk to grow even more. It is said that "time heals all wounds" but the unconditional love from a furry friend really helps pass the time. I'm also a house plant lover. If needed I can water and care for any houseplants during overnight sittings. No more worrying about your beloved pets or plants while you're away! With me you can have peace of mind that they're all in good hands. I'm currently unemployed. I have a very open schedule except for weekdays from Noon-1pm (when I dog walk in my neighborhood). I have 2 separate church events scheduled on the 4th Saturday of every month. Scheduling walks or drop in visits can be tricky that day because the events don't always have a set time. I can dog sit at your home on those 4th Saturdays as long as I am able to leave for a couple hours for the events. During drop-in visits/walks I rinse and refill water bowls, replace empty treat toys, clean up any accidents that may have occurred, play with your fur baby to release any pent up energy they might have, and complete any other duties you may have for me. I pay close attention during potty breaks and notify the owners if anything is out of the ordinary. When dog sitting I can stay at your home overnight if needed. If not I can check in as often as you'd like. I can provide updates through out the day and pictures so cute you'll want to frame them.

Sitter Profile Image: Brianna T.
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Brianna T.
from
$75
per night
5.0 out of 5 stars
2 reviews
7 years of experience
Merrillville, IN, 46410

About: I bring 7+ years of pet care experience, including working in a daycare setting where I cared for multiple dogs at once. I focus on safety, structure, fun playtime, and personalized attention to every during alone time. Making sure they feel comfortable, confident, and excited to see me. I am currently completing an externship for school, which takes place earlier in the day. I have open availability after 2pm on weekdays and flexible availability on weekends, making it easy to accommodate walks, drop-ins, and extended care as needed. I prioritize safety, comfort, and routine whether caring for pets in my home or a client’s home. I closely follow feeding schedules, leash guidelines, and any special instructions provided. I maintain clean spaces, supervise all interactions, and communicate updates regularly so pet parents feel confident and at ease.

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The median cost per night for house sitting in Winfield is $50

Pet parents share their Rover experiences - Winfield

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5.0 out of 5 stars

Margaret has been watching my pups and home a few times now and each time she has just been fantastic. Great communication, my house is always left very tidy, my pups are happy and well cared for and just adore her. Going on vacation is a breeze now that I have someone amazing to stay.

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amy c.
House Sitting
5.0 out of 5 stars

Gabby took such good care of our pups and our house while we were on vacation. 5/5. Highly recommend:)

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Allison M.
House Sitting
5.0 out of 5 stars

Gabby was wonderful. Our girls were happy and well cared for. We came home to everything great!! Would use her again. She’s the best!

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Betsy M.
House Sitting
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
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Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Winfield

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Sitters in Winfield average 4
repeat house sitting clients

FAQs for House Sitting - Winfield

Frequently asked questions about Rover

The average cost for House Sitting in Winfield on Rover is $49.95 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 517 sitters on Rover offering House Sitting across Winfield. 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 Winfield 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 Winfield 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 Winfield 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 Winfield. On Rover:

  • 88% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 97% 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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