House Sitting Winfield

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

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Over 42
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: April Y.
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April Y.
Star Sitter
from
$87
per night
5.0 out of 5 stars
55 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: Ashley H.
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Ashley H.
from
$60
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Crown Point, IN, 46307

About: I’ve owned pets my entire life, chose it as a career, and started working as a veterinary assistant. Now I work as a dog trainer! I’m excited to meet you and your pets! Right now I work part time, so I’m available most days in the afternoon/ evenings! I will have plenty of time to hangout with your fur babies! Let’s talk about the best day and time for you! The goal is to make sure your pups are happy and cared for as if you were home with them! I will always be prepared, always have treats, and always communicate with you!

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

This is long overdue. Hannah was very reliable and took great care of our two energetic pups while we were away. They absolutely loved her. She constantly updated us which puts our mind at ease while we were away on vacation. She is highly recommended.

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Emmanuel d.
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: David R.
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David R.
from
$50
per night
5.0 out of 5 stars
45 reviews
14 repeat clients
18 years of experience
Highland, IN, 46322

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: Natalie S.
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Natalie S.
from
$24
per night
5.0 out of 5 stars
5 reviews
1 repeat client
2 years of experience
Crown Point, IN, 46307

Natalie is amazing. She spent time getting to know our two dogs before house sitting and is a delight to chat with. She is dependable, responsible, respectful, and took the best care of the dogs (and the plants!). Very blessed to have found her and will absolutely rebook with her in the future.

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Allison M.
Sitter Profile Image: Gia C.
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Gia C.
from
$40
per night
5.0 out of 5 stars
2 reviews
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: Gillian C.
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Gillian C.
from
$40
per night
5.0 out of 5 stars
7 reviews
3 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: Rob S.
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Rob S.
from
$45
per night
4.9 out of 5 stars
40 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: 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: Tracy M.
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Tracy M.
Star Sitter
from
$145
per night
5.0 out of 5 stars
9 reviews
6 repeat clients
40 years of experience
Lowell, IN, 46356

About: House sitting, dog walks, training and drop in visits for all pets. I have cared for animals my entire life, from dogs and cats to small pets. I am actively training dogs with structured leash and behavior support during walks. I have raised puppies through two litters, so I understand the patience, attention and care they need at every stage. Animals have always been part of my family, loving companions and treated as such. I treat every pet I meet as I would treat my own. Whether it's walks, playtime, or keeping them comfortable in your home, I provide dependable, loving care that keeps tails wagging and the owners at ease. I know dogs thrive on routine, so I'm happy to provide weekly care at consistent times; walks, play or just someone to sit with while you're at work or on vacation. Premium overnight care for pets who deserve a calm, experienced caregiver. Thoughtful communication, respectful home care, and personalized attention while you're away. Daily walks are part of my own health and wellness routine, and caring for pets fits right in. Sadly, my own dogs have passed, and the right one hasn't come into my life yet. Until then, I would love the chance to share my time, energy and affection with other's people pets. Dogs especially bring me joy, and walking them keeps both of us happy, active and cared for. I'd like your dog to know me as their regular walking buddy. I follow each pet parent's instructions closely and respect their home. My focus is on your pet's safety and comfort, and well-being so you can feel confident they are cared for while you're away. I am available for consistent weekly walks, drop-ins, and over night house sitting.

Sitter Profile Image: Diane B.
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Diane B.
Star Sitter
from
$70
per night
5.0 out of 5 stars
47 reviews
16 repeat clients
40 years of experience
River Forest, IL, 60305

Diane is amazing! Our dog Juni is really tough. She's petrified of strangers and sometimes nips. She's very slow to warm up and sometimes won't even let sitters let her outside. There have been times when she boycotted eating for days, and even when we have family watch her, she's often sick for days after we get back because of stress. Diane worked with Juni and treated her with kindness, patience, and understanding. She gave her space and even did some emotion/body coding work with her which I thought was really cool. She treated our house with respect and we returned to it spotless. I felt very safe and comfortable having her stay in our home, and I think Juni did too. She was in great spirits when we got back and she even had a great few days of eating, no stress sickness. We so appreciate Diane's willingness to work with her! In addition, she was very communicative and thorough when it came to the details/logistics of the stay, and came by in advance to meet us and Juni. I would recommend Diane to anyone.

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Jennifer C.
Sitter Profile Image: Sydney H.
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Sydney H.
Star Sitter
from
$60
per night
4.9 out of 5 stars
18 reviews
3 repeat clients
6 years of experience
Saint John, IN, 46373

Sydney was a godsend with our 2 dogs. She met them twice before our trip since we have a nervous pup & she put her right at ease. I've never seen our girl be so good with someone so quickly. We got regular updates & pictures & I know that our doggies were in the best hands while we were gone. Will 100% be contacting her again! She's the best!

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Alyssa O.
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

We couldn’t be happier with our experience! Alexia went above and beyond to make sure Cinco was comfortable, loved, and well taken care of. Communication was excellent, and it gave us total peace of mind while we were away. We will definitely be using her again!

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Autumn C.
Sitter Profile Image: Mary S.
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Mary S.
Star Sitter
from
$50
per night
4.9 out of 5 stars
241 reviews
82 repeat clients
20 years of experience
Michigan City, IN, 46360

Mary was AMAZING!! She sent us a bunch of pictures of my service dog when we were in Hawaii for our daughter's wedding (the state wouldn't allow her entry). Nuela was in love with Mary by the time we got home! Will Definitely use her in the future if she's available.

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Lori S.
Sitter Profile Image: Gabriela L.
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Gabriela L.
Star Sitter
from
$20
per night
4.9 out of 5 stars
34 reviews
7 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: Annie X.
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Annie X.
from
$75
per night
4.9 out of 5 stars
159 reviews
114 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

Amazing!!! Annie is great with out shy dog and went out above to build trust with our dog. Annie was very good about communicating with us. We will definitely be using Annie as a pet sitter again!

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Angelina L.
Sitter Profile Image: Michelle G.
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Michelle G.
from
$90
per night
5.0 out of 5 stars
18 reviews
9 repeat clients
10 years of experience
Joliet, IL, 60435

Michelle is the best!! Our dog has some special requirements because she is reactive and Michelle is so so great with her. 1000% will want to book again and again with her!

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Brittany T.
Sitter Profile Image: Juana P.
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Juana P.
from
$25
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
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.

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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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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 - Winfield

Select a filter and find qualifying sitters offering house sitting.

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 August 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 August 2026, there are 519 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:

  • 91% 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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