House Sitting Highwood
Find a loving house sitter to watch over your pets and your home.
Over 53 pet parents in Highwood have booked house sitting
Highwood, 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.
“Dylan was very thorough obtaining all the information required to take good care of my dog. He was sensitive to my dog's needs and treated him appropriately. I will definitely use him again.”
“Sarah took care of our cat for four days at our house while we were away. He has to be given medication at certain times during the day and also loves human attention. Sarah was caring and responsible, spent time hanging out with him, and made sure he got his meals and medicine at the right times. She also checked in with us, asked good questions, and responded quickly when we checked in with her. We hope to hire Sarah again, and highly recommend her for petsitting and housesitting.”
“Marissa took wonderful care of our greyhound, Cash, while staying in our home. She was thoughtful, neat, and left everything very clean when we returned. Throughout her stay, she sent great photos of Cash, which gave us real peace of mind while we were traveling. Most importantly, Cash was very happy and well cared for. We were extremely pleased with Marissa and would absolutely recommend her to anyone looking for a reliable, caring, and respectful pet sitter.”
“Michael was fantastic! We have 2 large dogs, one has pretty bad anxiety, he handled him so well! He communicated, sent pictures, and really cared about taking care of our dogs! I would recommend him to anyone. He did some training with our dogs as well which helps with getting energy out, I just really appreciate how caring he was with our dogs!”
“Hope house sat and watched my dog while I was out of town for 6 nights. She was punctual, quick to respond, and sent daily updates (and also she was very friendly). Hope left my house as clean as when she arrived, and my dog was very happy with all of the attention and exercise she received. I would recommend Hope for house sitting in the future and will be happy to have her watch Kaya again!”
About: Growing up surrounded by pets, I developed a deep understanding of their needs, behaviors, and the patience required to make them feel safe and loved. Whether it’s daily walks, feeding, or just providing companionship, I treat every pet as if they were my own! I’m currently a senior at Dominican University so my flexible schedule allows me to adapt to different routines, ensuring that pets stay comfortable and happy while their owners are away :) With years of experience of caring for my own pets I understand the importance of following routines and recognizing pet behaviors. I like to talk to my clients about routines and dietary instructions before I take care of their furry friend to really get a feel for what is best for them. I have a pretty strict diet with my own dogs so I like to make sure I can trust someone to do the same as I would as well :) Pet owners can rely on me to be punctual, responsible, and communicative, giving them peace of mind knowing their furry friends are in trustworthy hands.
“Arianna was fantastic house sitting my two pets. She understood their personalities and took such great care of them while I was out of town for a work trip. Highly recommend!”
“Outstanding care. What more can you ask for when you leave your home and pets in someone else's care? That's what Donna delivered in spades. Donna was responsive, proactive, caring and considerate. She was in instant contact and everything was breezily coordinated prior to our trip. Once we left, Donna kept in constant communication and delivered on everything she said she would do. When I came home my pets were healthy and happy but I was stunned to discover how neatly everything had been left. 10/10, will ask for again, thank you, thank you, thank you, Donna.”
About: I’ve had dogs in my family since I was in elementary school. I’ve been responsible for things like feeding them, walking them, and taking them out at night and in the morning Right now, my only commitments are on Sunday mornings, when I teach religious school in Deerfield. I’m looking for my next full time job currently, and heard about Rover through word of mouth. I’ll take your dog out first thing in the morning and last thing before bed. I’ll feed them right after they go out in the morning, and before I have dinner myself. I’ll also walk them at least once a day, weather dependent
“I was terrified about finding someone to watch my little Velcro baby. But Rebeca put me at ease. Her communication with me and love she gave my baby is beyond what I could have expected. I am so happy to have book with Rebeca and next time I am in Chicagoland I will definitely book with her again! Thank you Rebeca!!!”
“Katelyn was great with our fur babies! She sent plenty of photo updates throughout the booking. She updated us about anything going on with the kids and asked questions along the way. We really appreciated her communication! The dogs loved her during meet and greet. I’m sure they wanted her to stay with all the doggy cuddle puddles! Would definitely book her again! It was so reassuring to have someone reliable, communicable, and compassionate. Made our vacation a breeze. We missed our doggos, but didn’t have to worry or stress with Katelyn!”
“Jennifer took such great care of Ref while we traveled for spring break. She took him on multiple walks a day, spent quality time playing with him, and even went above and beyond by helping with laundry. It gave us so much peace of mind knowing he was not only well cared for, but truly loved while we were away. We came home to a happy pup and a spotless home, couldn’t ask for more. Highly recommend Jennifer!”
About: I have spent my whole life surrounded by dogs. I grew up with dogs and grew up caring for them, walking them and cleaning up after them. As a college athlete. I am looking to help out the community any way possible. I think my active lifestyle can translate well with what it takes to be successful in Rover. I have a high motor and am an extremely determined hard worker. I care for pets as if they were my own, with a strong focus on safety, consistency, and respect for each client’s home. In clients’ homes, I follow all care instructions closely, including feeding routines, walk schedules, leash preferences, and any behavioral or medical needs. I make sure dogs get attentive, unrushed walks with plenty of positive reinforcement and appropriate exercise based on their age and energy level.
About: I have been an animal lover my whole life and have had pets since I was 5 years old. I currently have two cats who I am the primary care giver. My late dog, Mara (a black lab), became diabetic when she was 11. For the last 3 years of her life, I administered her insulin shots twice a day. From March 2019-March 2020, I volunteered at CARE Skokie and have watched friend’s cats and dogs over the years while they were away. Animal welfare means a lot to me and I understand the importance of providing consistent and loving care. I would love to have the opportunity to be of service to you and your four-legged family member(s)! I recently resigned from my job in Wealth Management and am focusing on doing things that are more fulfilling and I love animals. I am currently working part time at a local garden shop and have a flexible schedule that allows me time to tend to your pet(s) as needed! I grew up with a dog and have two cats at home who I am the primary care giver for. I am an advocate for all animals to be well taken care of and understand the importance of their needs being met through consistency and loving care.
About: Hi! I’m an animal lover with experience caring for dogs and cats of all ages, breeds, and personalities. I grew up with two dogs of my own and have since had the opportunity to pet sit for many different kinds of animals. One of my most memorable experiences was caring for 10 newborn puppies by myself, which taught me just how much patience, attentiveness, and responsibility goes into caring for animals. Whether I’m looking after a playful puppy, a senior pet, or a cat who prefers to do their own thing, I always take the time to understand each animal’s individual needs and personality. For me, the most important part of pet sitting is building trust, both with your pet and with you. I want you to feel completely comfortable knowing that your animal is safe, happy, and well cared for while you’re away. I treat every pet like they’re my own and would love the opportunity to care for your furry friend! I work remotely, which gives me a flexible schedule and allows me to work around your pet’s routine and needs. I’m happy to accommodate your preferred feeding, walking, playtime, and care schedule whenever possible. Your pet’s safety and your peace of mind are my top priorities. I’ll carefully follow your instructions, learn your pet’s routine and personality, and keep you updated with photos and messages so you know they’re happy and safe.
About: I've owned two dogs and cared for both from puppyhood through their senior years, so I'm familiar with the different needs that come with each stage of life. My second dog also managed to get into more than a few unexpected situations, which taught me to pay close attention, stay calm, and recognize when something doesn't seem right. In addition to caring for my own dogs, I've dog sat for a number of others, each with their own personalities, routines, and preferences. I know every dog is different, and I enjoy getting to know what makes each one feel comfortable and happy. I treat every dog in my care like they're my own and always do my best to make sure they feel safe, loved, and well cared for while you're away. I currently work at Starbucks as a supervisor. I have semi-flexible hours and given enough notice I can make myself more available. (3 or so weeks) I always work try and work my schedule around yours. I typically work 8 hours a day and can’t usually step away to do a pop in during that time. I always strive to leave your home as you left it and your pups happy to see you arrive home again! If you need me to do house duties while I’m there I will do my best to assist with it.
The median cost per night for house sitting in Highwood is $55
Pet parents share their Rover experiences - Highwood
Bryn has been my dog sitter twice and each time has done an amazing job. My dog Bruno is a very large Bullmastiff and she had no issue watching him and it’s very obvious Bruno feels comfortable with her. She’s conveniently close by and does a great job communicating and keeping me posted on how things are going. I will continue to use Bryn in the future when she’s available. Five Stars!!!!
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.
How to book house sitting
1. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Highwood
Select a filter and find qualifying sitters offering house sitting.Sitters in Highwood average 4 repeat house sitting clients
FAQs for House Sitting - Highwood
Frequently asked questions about Rover
The average cost of House Sitting in Highwood is $56 per night as of November 2026. Most bookings cost between $41 and $70 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 7,474 sitters on Rover offering House Sitting across Highwood. 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 Highwood 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 Highwood 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 Highwood 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Highwood. On Rover:
- 87% of sitters can help with special care needs
- 91% can help with giving oral medications or injections
- 95% 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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