House Sitting Winfield

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

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Over 30
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: Jedidiah A.
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Jedidiah A.
from
$50
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
12 years of experience
Wheaton, IL, 60187

I can't recommend Jed highly enough! He truly saved the day by accepting my booking at the very last minute. He was incredibly accommodating, friendly, and professional. Most importantly, Mazi adored him. I will definitely be booking with him again!

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Esther C.
Sitter Profile Image: Ash B.
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Ash B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
197 reviews
63 repeat clients
7 years of experience
Wheaton, IL, 60189

Ashley was perfect for our nervous little girl!! Loved the updates and how prompt she was with her schedule. Will definitely use Ashley on future vacations!

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Caitlin N.
Sitter Profile Image: Amanda R.
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Amanda R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
24 reviews
6 repeat clients
5 years of experience
Naperville, IL, 60563

Amanda was extremely conscientious and caring while pet sitting our Golden, Addie!! She sent multiple pictures and updated us in our absence! We knew how much she enjoyed every moment with our dog. Thank you, Amanda!!!

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Nancy L.
Sitter Profile Image: Gavin S.
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Gavin S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
7 years of experience
West Chicago, IL, 60185

Gavin took care of our three dogs while we were away for a few days. He made sure they were fed, let outside, and cared for during our trip. We appreciate the time and effort he put into looking after our pups and helping us while we were out of town.

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Silvy A.
Sitter Profile Image: Sydney B.
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Sydney B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
5 years of experience
Winfield, IL, 60190

Sydney (Grace) was incredible with our boy, Sonny! He can be a little reactive on leash sometimes, so we were a little nervous about who was caring for him. Grace went above and beyond to make us and Sonny feel comfortable. She sent updates and pictures every day. Sonny absolutely loves her! We would recommend her to anyone.

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Katie C.
Sitter Profile Image: Mia M.
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Mia M.
Star Sitter
from
$40
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
5 years of experience
Naperville, IL, 60563

I was hesitant since this was our first booking, but mia put me at ease right away during the meet and greet. She was responsive, communicative, and considerate. Came home to such a clean house - and happy pets! Would book again.

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Lori T.
Sitter Profile Image: Luis A.
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Luis A.
from
$55
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
7 years of experience
Naperville, IL, 60563

About: My parents have a farm with three big dogs and many small ones, I’ve taken care of them many times over the years. I have neighbors and friends reaching out to care for their furry friends while they are out of town. I promise to give your loved furry one the love they would expect on a day to day basis I work from home so if I need to spend the day with your pet I can be there for them as I work! Outside of work hours I can give long walks and tons of play time. If you pet needs extra attention I can provide lots of head pets or give them space if they like to spend their time alone.

Sitter Profile Image: Bonnie D.
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Bonnie D.
Star Sitter
from
$70
per night
5.0 out of 5 stars
149 reviews
31 repeat clients
20 years of experience
Naperville, IL, 60563

Bonnie is amazing! Trustworthy and loves dogs. Bonnie watched our 2 dogs in our home for 10 days. Will be booking Bonnie again very soon. Thank you Bonnie!!

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Renee G.
Sitter Profile Image: Katherine B.
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Katherine B.
Star Sitter
from
$70
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
4 years of experience
Glen Ellyn, IL, 60137

Katherine stayed with our two dogs over Memorial Day weekend. She kept us updated, shared pictures, handled their allergy meds and somewhat complicated food situation, and was overall lovely to work with!

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Jake & Carlie B.
Sitter Profile Image: Glen S.
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Glen S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
134 reviews
57 repeat clients
14 years of experience
Naperville, IL, 60540

I had a great experience with Glen as my dog sitter. He was extremely reliable and attentive, especially when it came to administering medication, including eye drops, to my dogs. Not only did he take great care of my dogs, but he also kept the house tidy. I really appreciated how he sent frequent updates and pictures of my dogs, which put my mind at ease while I was away. I would highly recommend Glen to anyone in need of a trustworthy and caring dog sitter.

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Rachel M.
Sitter Profile Image: Abaigeal & Karen B.
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Abaigeal & Karen B.
from
$60
per night
5.0 out of 5 stars
18 reviews
2 repeat clients
18 years of experience
Wheaton, IL, 60189

Karen was absolutely amazing with our three dogs while we were away. Each of our pups has different needs, including one senior dog who requires medication and extra attention, and Karen handled everything with such care and compassion. She kept us updated throughout our trip with lots of pictures and videos, which gave us so much peace of mind. When one of our dogs wasn’t feeling well, she went above and beyond to make sure she was comfortable and well cared for. It was clear from every update that she genuinely loved and cared for our dogs as if they were her own. Coming home to happy, well-cared-for pups was the best feeling. We are so grateful for Karen and would highly recommend her to anyone looking for a trustworthy, attentive, and caring sitter. She truly went above and beyond!

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Silvy A.
Sitter Profile Image: Lee G.
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Lee G.
from
$50
per night
5.0 out of 5 stars
3 reviews
25 years of experience
Wheaton, IL, 60189

Leeann was wonderful with Mia and Pio! She came on time and cared for them as if they were her own. She sent photos through the day and communicated as requested. Both Mila and Pio were in great spirits when I came home. They took several walks and played puzzles. I’d highly recommend Lee to watch your pets!

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Peg H.
Sitter Profile Image: Michael J.
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Michael J.
from
$70
per night
4.8 out of 5 stars
5 reviews
10 years of experience
Wheaton, IL, 60187

About: I've taken care of cats and dogs for over 10 years for friends and family. I love animals, and bring a strong sense of care and joy to my work. I am a college student who is off for the summer, seeking gig work to pay the bills. I have a lot of free time. I treat clients with privacy and treat their homes as I would treat my own. The safety and well being of their pets is my first priority.

Sitter Profile Image: Grace A.
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Grace A.
from
$30
per night
5.0 out of 5 stars
4 reviews
1 repeat client
6 years of experience
Lombard, IL, 60148

Grace was AMAZING with Maple! Lots of picture updates while we were away and great communication. You can trust Grace to provide fantastic care for your pet!

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Brendan H.
Sitter Profile Image: Maria C.
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Maria C.
from
$45
per night
4.9 out of 5 stars
13 reviews
5 repeat clients
7 years of experience
Glen Ellyn, IL, 60137

Maria did a wonderful job taking care of Hazel and my two cats. She sent lots of pictures and daily updates, which allowed me to enjoy my vacation and not worry about my pets. Thank you!!

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Erin T.
Sitter Profile Image: Annika & Grant S.
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Annika & Grant S.
Star Sitter
from
$55
per night
4.9 out of 5 stars
23 reviews
12 repeat clients
20 years of experience
Carol Stream, IL, 60188

Grant and Annika did great with our senior dog and puppy. They are both rescues and nervous boys and require some specific attention including medication administration. They took care of our home and we came home to clean sheets and a house that was cleaner than we left it.

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Hannah W.
Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
121 reviews
25 repeat clients
4 years of experience
Lombard, IL, 60148

Ashley was great!! I had no worries about leaving my dog with her and she did such a good job at updating me throughout the day and responding quickly! Will 100% use her again if I need to!

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Michele R.
Sitter Profile Image: Melissa P.
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Melissa P.
Star Sitter
from
$60
per night
5.0 out of 5 stars
53 reviews
11 repeat clients
20 years of experience
Glen Ellyn, IL, 60137

Melissa is amazing! She treated our dogs like they’re her own. They felt so comfortable with her and loved snuggling with her! She was also so accommodating. Anything we asked of her, she never hesitated. We will definitely have her dogsit again!

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Wendy K.
Sitter Profile Image: Paula K.
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Paula K.
Star Sitter
from
$130
per night
5.0 out of 5 stars
70 reviews
16 repeat clients
10 years of experience
West Chicago, IL, 60185

Paula did an amazing job with Ozzy! We would definitely have her watch him again in the future.

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Jacob P.
Sitter Profile Image: Leila P.
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Leila P.
from
$80
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
8 years of experience
Wheaton, IL, 60189

About: I’ve had pets my entire life and grew up caring for both cats and dogs. Throughout childhood, my family had a cat and we frequently dog-sat for multiple dogs. In college, I continued pet sitting as a side job and gained even more hands-on experience. I regularly care for friends’ and family’s dogs when they travel. I’m comfortable with pets of all sizes, breeds, and ages, and I genuinely love animals. I especially enjoy walking dogs and making sure they get plenty of exercise, attention, and affection. I am available Friday-Sunday. I am work from home Friday, so I can help out during the day, and through the weekend. I am flexible to your schedule! When caring for pets in their own home, I focus on keeping their routine and environment consistent so they feel safe and comfortable. For drop-in visits, I make sure pets are fed on schedule, have fresh water, and get plenty of attention and playtime (my favorite!). I always check that doors, gates, and crates are secure before and after visits. I am extremely responsible as I have cared for pets my whole life. For walks, I use secure leashes and harnesses as instructed by the owner and stay aware of my surroundings at all times. I avoid unsafe areas, watch closely for other animals, and make sure each walk matches the pet’s energy level and needs. I have experience with all sizes of dogs. I treat every home and pet with respect and care, follow all owner instructions closely, and provide updates so pet parents feel confident their pets are safe and happy. I would love to care for your pet!

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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

Grant and Annika did great with our senior dog and puppy. They are both rescues and nervous boys and require some specific attention including medication administration. They took care of our home and we came home to clean sheets and a house that was cleaner than we left it.

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Hannah W.
House Sitting
5.0 out of 5 stars

Sydney (Grace) was incredible with our boy, Sonny! He can be a little reactive on leash sometimes, so we were a little nervous about who was caring for him. Grace went above and beyond to make us and Sonny feel comfortable. She sent updates and pictures every day. Sonny absolutely loves her! We would recommend her to anyone.

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Katie C.
House Sitting
5.0 out of 5 stars

Gavin was terrific! We hired him to watch our senior Yorkie for two nights in our home, and he was so wonderful! He was communicative, wasn’t afraid to ask for clarification about instructions, and sent us sweet photos and videos of our dog while we were gone! He was gentle and loving to our dog and took excellent care of our home as well! I highly recommend him!

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Jessica W.
House Sitting
5.0 out of 5 stars

Abbie and Karen take fantastic care of our Bernese mountain dogs. They make sure our boys are fed, pottied and played with and are great sharing photos and videos with uz. We are so grateful for their help and will continue booking with them!

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Nicole P.
House Sitting
5.0 out of 5 stars

Megan was responsive and did a great job with our lab puppy! He can be high energy at this age, but she let him run around a bunch in the yard and tired him out. We were grateful to know someone was watching him while we were away and that he was safe and cared for!

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Lana D.
House Sitting
5.0 out of 5 stars

We appreciate Alex watching our two cats in such short notice. He was a great sitter and home guest.

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Audrey W.
House Sitting
5.0 out of 5 stars

Jessica did a wonderful job and all the pets were well cared for! I received daily updates and pictures. I recommend her to others and will request her again!

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Darcy R.
House Sitting
5.0 out of 5 stars

Jack is excellent. My pups loved him. As a fellow Rover Sitter myself, I highly recommend him and hope to use him again in the future.

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Pamela R.
House Sitting
5.0 out of 5 stars

Jacob gave us peace of mind during a crazy weekend while he looked after our pets and stayed with them. He shared so many great pictures and kept me updated the whole time. I would gladly book him again! Thank you so much!!!

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Stephanie C.
House Sitting
5.0 out of 5 stars

Doggos seemed to have a great time and the house was in excellent condition when we got back! We really appreciated Emma's attention to detail and she was easy to stay in contact with while we were across the country.

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Jalen and Taylor M.
House Sitting
5.0 out of 5 stars

We are so appreciate Crissy was able to stay with Cyrus on such short notice and take care of him while we were away. She was very communicative, spent lots of time with him, and even went above and beyond by trying to take him for a walk, which is no easy feat. It was apparent that she genuinely cared about his well-being and we could tell he wasn’t lonely when we returned. Would definitely recommend her to anyone looking for someone to care for their pet!

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Sarah G.
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

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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 $54.95 per night (as of July 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 July 2026, there are 8,424 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:

  • 93% of sitters can help with special care needs
  • 95% 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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