Pet Sitting Chesterland
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 19 pet parents in Chesterland have booked pet sitting
Chesterland, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I have owned and cared for more than 50 animals in my 38 years 🥰 I currently have a 3 year old cat, a 2 year old cat, and a 1 year old cat. I had 2 dogs over the course of almost 19 years (12 years old and 16 years old when they passed). I grew up with skunks, cats, dogs, hamsters, lizards, and more. I also have been fostering with local rescues for more than 10 years. Overall, I am just a big animal lover and find joy in watching other people's fur babies 🥰 I work from home full time, which allows me to have a flexible schedule. Evenings, weekends, and overnights can also be arranged. If you need anything overnight I prefer to stay at your home with your pets so they are comfortable and can stay in their normal routine. Let's discuss your needs! I am happy to follow whatever instructions you have for me to care for your furbabies! I know each pet is different. Generally, dogs go out to potty several times a day, as well as need fresh food and water daily. Cats also need fresh food and water daily, plus cleaning their litter boxes at least once a day.
“Alexis was a great care taker for our dachshund over the weekend! She was very open and receptive to any specific requests we had, shared pictures and videos. Overall our dog appeared to enjoy the time with her and we would definitely reach out again the next time we are out of town.”
“She stopped by for a check in on my dogs while we were out of town. My dogs absolutely loved her, she was very responsive on needs that needed to happen for my dogs and even sent pictures of them! Would definitely recommend her to anyone needing their dogs taken care of!”
“Joel is awesome. Super nice guy, good communicator, easy to work with & has taken great care of our pup. Gives solid updates at the end of each visit. He goes above and beyond while dropping in at your house. For example - our dog got into our garbage before one visit & Joel cleaned up all the trash off the floor. We appreciate the care he takes in looking after our pup as well as our home. Definitely recommend!”
“Courtney has been a phenomenal cat sitter. I've booked with her many times and I've been exceptionally pleased every time to her care, attention, and thoroughness of visits. Plus, my cat realllly likes Courtney, which is always a plus! Wonderful experience, highly recommend :)”
“Terry is a caring and attentive cat-sitter that we were delighted to have watching over our 5 cats. It’s not easy to handle the various food patterns and routine that each of our babies prefer, but she handled it with ease and kindness. We cannot say how much we appreciated her - she gave us detailed updates and made sure everyone was comfortable and happy while we were out for a week. Thank you!!”
“This is the second time we've booked with Makenna, and I'm yet again a happy customer! She's done a house sitting and drop in visit with fantastic through updates. I feel relieved she's taking such great care of my dog and cat.”
“Melanie was very responsive, kind and professional! She took great care of your two pups while we were out of town. Easy to coordinate with and look forward to working with her in the future!”
“Everything went super smoothly! I would highly recommend Celine, she took the time to ask questions and get to know our pups and was very helpful. Looking forward to booking her again!”
“Matthew did a great job with his drop in visits with Archie while I was working and my husband was away. Matthew was very timely and great at communicating. Archie enjoyed his time with Matthew and I look forward to booking him again!”
About: I’ve taken care of dogs since I was 11 years old whether that be my own or someone elses, and I’ve had a passion for training and raising service dogs as well. I plan to do so through multiple programs in college. The nights on weekends could be a little difficult as I work another job however anytime during the week I will more likely than not be overjoyed to take care of your special boy/girl. I always make sure the dogs are more comfortable than I am. It’s their home, they are always fed, walked, and cared for as if they were humans.
“Beth was wonderful! She came twice a day to feed/water/scoop for our two kitties while we were away. We received lots of updates and photos. The cats loved her and we were very happy with her care.”
“Brandon was great! I knew he was going to be great fit since the meet and greet. Our dog Benji loves him. Milo will take a bit of time but I'm sure over the next few visits Brandon will win him over too.”
About: Dogs have always been a big part of my life. When a couple of years ago we lost our senior family dog, I started volunteering with a local rescue and have fostered 20+ puppies over the past few years. Fostering has given me experience with everything from energetic, playful pups to post-surgery care—things like baths, basic grooming, medications (even injections), vet pickups, and lots of patience and love. I also help neighbors with dog walking and pet sitting, so I’m used to different personalities and routines. I truly just love being around dogs—and getting outside for walks is a bonus for me too! I’m available for afternoon and evening walks or check-ins during the week. On weekends, I have much more flexibility and I am available throughout the day for walks, check-ins, or multiple visits if needed. I’m also happy to stick to your dogs’s usual routine to keep them comfortable and happy. Your pet’s safety and comfort are my top priorities. During walks and check-ins, I follow your instructions closely, keep dogs secure on leash, and make sure they get the right balance of exercise, attention, and care. I’m attentive, reliable, and treat every pet like my own.
About: Hello! My name is Shawntel and I have been an animal lover for as long as I can remember. Growing up, my family had 2 dogs and 4 cats. Now I have three dogs that I couldn't imagine my life without them, with two of them being rescues. When I’m booked for house/dog sitting, my dad gets to stay and spend time with his grand-pups (: One is a German Shepard mix, another one is a Pitbull, Husky, Lab mix, and my newest addition is a golden doodle! The German Shepard is a senior so I am used to making accommodations for animals as well as giving mediations. It doesn't matter if they are young or old, big or small, boy or girl-- I love them all. I am currently a first grade teacher in Lake County which I recently took time away from dog sitting to focus on my new position. But now I’m back!! So I am available before and after the school day during the week for your animals and pretty free on the weekends. I am usually pretty flexible so if you need anything special for your animal, just let me know! I also dedicate my summers and school breaks to house/dog sitting! I truly believe that a well taken care of animal is a happy one, and who doesn't want their fur baby happy?! I look forward to meeting you and your sweet animal(s)!! I am currently a first grade teacher in Lake County which I recently took time away from dog sitting to focus on my new position. But now I’m back!! So I am available before and after the school day during the week for your animals and pretty free on the weekends. I am usually pretty flexible so if you need anything special for your animal, just let me know! I also dedicate my summers and school breaks to watching animals! I truly believe that a well taken care of animal is a happy one, and who doesn't want their fur baby happy?! I look forward to meeting you and your sweet animal(s)!! I know animals feel most comfortable in their own home so I mainly watch animals in the clients home. I do my best to give them the love and attention you give them while you are away.
“Molly was amazing! Upon doing meet and greet you could tell she was professional and reliable. She was quick to communicate and great with sending updates. You could tell she really cares about your pets. Will definitely book with Molly again!”
“Paula is my go-to for a while now and am so happy to have found her! I have had to run out of town a couple times now on short notice for sudden family matters and with Paula, the dogs are the one thing I don't have to stress about! I know they are taken care of and happy pups! She has bailed me out a couple of times now and I can't thank her enough! She even left me and the dogs a Christmas card the last time... so thoughtful of her! If you need someone for an upcoming weekend, I highly recommend her!”
The median cost per visit for pet sitting in Chesterland is $20
Pet parents share their Rover experiences - Chesterland
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?
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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.
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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. Search
Browse profiles of sitters near you who offer pet sitting
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Popular requests for pet sitting - Chesterland
Select a filter and find qualifying sitters offering pet sitting.Sitters in Chesterland average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Chesterland
Frequently asked questions about Rover
The average cost for Pet Sitting in Chesterland on Rover is $16.05 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .
As of August 2026, there are 2,256 sitters on Rover offering Pet Sitting across Chesterland. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chesterland stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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 .
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.
Yes, you can find sitters who have experience with handling special pet needs in Chesterland. On Rover:
- 96% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 96% 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.
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.
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