Dog Sitting Chesterland
Book a Chesterland dog sitter to watch your dog in your sitter’s home or yours.
Over 15 pet parents in Chesterland have booked dog sitting
Chesterland, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: Hi my name is Yocheved, but a lot of people call me Yo, or Ava. I am an only parent to a wonderful, active middle schooler. We have a happy home full of love and laughter, and 2 kitties. After 14 magical years together, we lost our dog to old age, a couple years back. I miss the feel of having a dog around, but I know in my heart of hearts we are all a little older, and a little busier, and our home cannot house a new permanent four-legged resident. But I do not accept the lack of dogs in our lives! I said yes to dog sitting lately, and I have made so many new friends since. Hanging out with your dogs or cats when you're unable to be there- it's become a thing I look forward to in my home. I love walking the neighborhood or doing drop-ins to feed cats. Let me help you! I'm currently WFH part time, and tend to end my days on the early side, for parenting purposes. Because of this I'm pretty flexible and available throughout the week. I tend to all pets, like I would for my own. I cared for my dog through cancer, twice- so I'm pretty familiar with medicine, senior care, and all the extra effort needed for older or sick animlas. I love to walk, burn off energy, and snuggle. Happy to do light grooming (brushing), and send photos and videos throughout our time together!
“We had a wonderful experience with Elinor as our cat sitter! She was a great communicator from our initial request through her very last visit, which gave us a lot of peace of mind while we were away on an extended trip. Our cats don't always come out for strangers, so we were especially happy to see that they warmed up to her enough to come out for treats and even play with her during some of her visits. She sent us cute photos and thoughtful updates each day, which we really appreciated and loved seeing while we were away. Our flight home was unexpectedly delayed, and she was incredibly flexible about adding an extra day with the girls. It was such a relief knowing they were in good hands. We would definitely use her again and would highly recommend her to anyone looking for a reliable, caring, and communicative pet sitter!”
About: While growing up, I fed, watered, played with, and walked our family friends. I even picked up poop! As an adult, I've done it all, from cleaning major messes to administering meds. I love canines and felines of all varieties, from the smallest to the largest! I am available to care for your pet(s) throughout the business day. Although I am also doing some volunteer work, I keep a regular schedule. I will care for your pets according to your express instructions. They will be treated as my own with as much love and concern as I can provide.
“Respectful and Professional, got along great with my precious creature. Followed instructions perfectly, and reached out when needed. Could stand to be more assertive w/ dogs sometimes, but still a great sitter. 10/10 would book again :)”
“Anthony has been checking on my dog Cooper while I’m at work for about two weeks. He is great and very knowledgeable with dogs. He makes sure Cooper lets out some energy and takes him on walks. Highly recommend his business.”
“Nicole did a great job dropping in to visit my puppy, Luna, during the day while I was at work. Nicole did drop-in visits for several months, and she was always on time and was super easy to communicate with, even if I had to cancel last minute. I highly recommend Nicole for drop-in visits!”
“Our puppy loves Isabella! She goes above and beyond when visiting Rocky, playing with him, and taking him for a walk. We definitely recommend Isabella and will continue to use her service in the future.”
“Adara was absolutely wonderful with Javi and Tamale! From the start, it was clear she genuinely cares about the dogs in her care — she was attentive, gentle, and really listened to everything I shared about their needs and routines. The regular updates she sent gave me total peace of mind while I was away. I came home to two happy, relaxed pups, which says everything. We will 100% be booking with Adara again — highly recommend her to anyone looking for a sitter who treats your pets like her own!”
About: I have taken care of dogs and cats since l was 10, with friends, family, and neighbors asking for pet care since l remember. I always enjoy spending time with furry loved ones. I care for two of my own dogs so it’s an everyday routine for me to care and check in on them when I do have to leave the house. I don’t have a job that requires me to be on site all the time so it’s perfect for my dogs schedule now that I have more time to be around them. At home I watch my dogs everyday, they are well trained so I don’t have to be super vigilant on them because I know them won’t leave the yard. They are fed twice a day and I try to walk them everyday. As for a clients home it depends on their schedule and how they care for their dog, but whatever their dogs needs are I will provide the service of fulfilling it.
“Joel provided drop in visits for a week while we were on vacation and if we could give him 10 stars out of 5 we would. He is prompt, caring, follows up very quickly with availability and answering questions, and we recommend him to anyone looking for a pet sitter. His flexibility helped us a ton as our request was last minute and we felt a little scattered with our plans. We felt very comfortable, our new kitten loved him and he is extremely knowledgeable! Also, he met with us prior to watching Pearl and answered all our questions. Highly recommend!!”
“Paula is great! She has been my go to for a number of years now. My pups love her and our new cat now too! She always sends photos of the wagging tails which puts me at ease while I'm gone. I know I can rest at ease knowing Paula is on the job!”
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: I have been a pet owner and lover my entire life since I was a young girl I C always wanted to take care and charge of my family pets I have had numerous pets at a time I offer my full attention and love and concern always take my dogs to vets for any reasons any concerns because I want them extra healthy. I love dogs The most but I do enjoy all animals the same. I take pride in my care and affection and dedication to all dogs and their happiness every single day they make my day and so many others day a better day. Happy to serve your dogs any way I can! I am currently self employed I can work any time my schedule is very flexible I can visit and watch as many times as you need I’m very open and available for you. I have my dogs to attend to as well as yours:) I have a chain and fence for my dogs and my dogs are well trained they hardly even need any chain. I watch for any other dogs for possible interactions. I can walk yours I have a large neighborhood i with lots of space or yours as well
“Great with our dog, Stella. Briana was patient and kind as Stella became adjusted to a new person. She sent photos of Stella’s activities, which was appreciated. We have already scheduled Briana to come again!”
“Kelsey was so helpful in caring for my 6 week old kitten! She was communicative and sent pictures when she checked on him, everything was tidy when I got back home too. Thanks so much! :)”
About: growing up with a family dog, i’ve always looked forward to our long walks! since i've moved to care for my grandma and can’t have a pet at my current home, i’m looking to be the dedicated adventure buddy your pup deserves! i’m an avid walker who cleans up after your pet and loves exploring local parks and trails. i’m just as comfortable handling a brisk, high energy trek as i am a slow, 'sniff heavy' stroll for seniors or 4 legged friends who love getting distracted! all sizes welcome: i absolutely love dogs of all sizes, from tiny pups to extra large breeds. if you have a giant dog, you are in safe hands here! being a taller, sturdily built person gives me a natural physical advantage and a grounded presence :) i don't get easily knocked off balance or intimidated by heavy pullers, meaning your big dogs get the steady, confident, and secure handling they need! hot weather: for dog-friendly clients, i am able to provide low-stress trips to uncrowded, pet-friendly stores/facilities for stimulation and enrichment (including a potty break outside before and after, of course!). i am also happy to walk earlier/later in the day to avoid the heat as well! i also enjoy keeping pets company in-home, whether it's playing with toys, using lick mats, or just spending some time together! my growing services & training: i am now certified in dog training, and offer a train & walk bundle if you're interested!! :) my ultimate goal is to become a true one-stop shop for your dogs, so i am also currently working toward learning professional grooming to add to my services soon! because i work evening and overnight shifts, i have guaranteed availability every morning and midday for your dog’s routine. whether you need a recurring daily walker or a same-day visit because you’re running late, i'm local and ready to jump in! my current job is closing in a few months, so i’ll be even more available for your schedule soon :) in public, i use a short-leash grip, stay hyper-aware of our surroundings without distractions like phones/technology of any kind (aside from photos, of course!), and avoid unknown dogs to keep your pup protected. i pride myself on being a trustworthy, punctual communicator, providing frequent photo updates so you’re always in the loop. i am very confident in my ability to kennel/leash pets & i consider myself well-versed in administering medication. i am keen when reading animal stress signals, ensuring your pet feels safe and understood under my care! as of august ive completed my initial dog training certification and continue learning to better my understanding and confidence in dog training :)
About: I’ve always loved animals and enjoy giving pets the attention, care, and companionship they deserve. I’m comfortable caring for pets in their home, taking dogs on walks, and stopping by throughout the day for meals, potty breaks, playtime, and plenty of love. I understand that every pet has their own personality, routine, and needs, and I’m happy to follow your instructions to keep them comfortable and on schedule. Whether your pet needs an energetic walk, some company while you’re away, or a little extra attention at home, I’ll treat them like they’re my own. I’m reliable, communicative, and will keep you updated with photos and messages so you can feel confident your pet is happy and well cared for while you’re away. **For first time visits please book at least 3 days in advance so we can make sure we can schedule a meet & greet** I work remotely, which gives me a flexible schedule and allows me to be available for walks, drop-ins, and house sitting throughout the day. I’m able to work my pet-care schedule around my meetings and work responsibilities, and I’m happy to coordinate with your pet’s routine and needs. I’m especially flexible for daytime walks and drop-ins, as well as house sitting when needed. I’ll always make sure I have plenty of time to give your pet the attention, exercise, and companionship they need while still keeping up with my work commitments. I treat every pet like they’re my own and make sure they feel safe, comfortable, and cared for in their usual routine. I’m happy to follow your instructions for feeding, walks, medication, playtime, and any other special needs or preferences. Since I work remotely, I’m able to be flexible and provide plenty of companionship throughout the day while working around my meeting schedule. For walks and drop-ins, I’ll make sure your pet gets exercise, attention, potty breaks, and plenty of love. For house sitting, I’ll keep their routine as consistent as possible and make sure they’re never without the care and companionship they’re used to. I’ll also keep you updated with photos and messages so you can relax knowing your pet is happy and well cared for.
The median cost per visit for dog sitting in Chesterland is $20
Dog parents share their Rover experiences - Chesterland
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- 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.
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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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Popular requests for dog sitting - Chesterland
Select a filter and find qualifying sitters offering dog sitting.Sitters in Chesterland average 7 repeat dog sitting clients
FAQs for Drop-In Visits - Chesterland
Frequently asked questions about Rover
The average cost for Dog Sitting in Chesterland on Rover is $16.05 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .
As of September 2026, there are 2,154 sitters on Rover offering Dog 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.
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 Chesterland 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!
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.
A Meet & Greet is a short introductory meeting between you, your dog, 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Chesterland with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
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.
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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