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: I have been a volunteer at Lake Humane Society for 2+ years, and I also worked on their adoption team for over a year. I have also been pet sitting for friends and family for many years now, and I also own cats and fish!! I am currently available for pet sitting Monday through Friday, and I can also manage some weekends as well, and if needed I can do some holidays! I have experience with dog crate training, experience with giving dogs and cats medication, and I am also able to walk dogs, let them outside in a fenced area, or put them on outdoor leads. I also have lots of experience feeding multiple animals at a time as well.
“Nicole did a fantastic job caring for our pets! She came by twice to feed our dog Kashi and our cat Bumper, and made sure Kashi got time to run around and go potty. Everything was handled exactly as we asked, and we came home to happy, well-cared-for pets. Nicole was friendly, reliable, and clearly loves animals — we’d happily book her again and recommend her to anyone looking for a trustworthy sitter.”
“Elinor was amazing! She just love cats! The way she connected with our boys was just impressive! They loved her since the first day!! For us it was a relief, knowing that they liked her! Every time she played with them, gave a lot of pets!! That makes a difference. And she took care of my plants and tomatoes :) I wont hesitate to book with her again! Cause I know that our boys will be in good hands!!!! I only have good things to say about her!!! I appreciate all she has done while we were gone on vacations!”
“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.”
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!
“Ben really helped us out when we were in a bind for Christmas. He sent us a ton of pictures of warner which we love. He spent time with both our cat and dog, which wasn’t required, but he went above and beyond. We are so grateful! Thank you Ben!!”
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.
About: I have been rescuing & caring for animals for some time now, I have had experience with older animals and younger animals, with bottle feeding to giving them the medical care they need. My weekly routine in consistent and mostly flexible throughout the week, which makes it easier to tie things in between. Work and daily priorities. Pet sitting is where my main ideal routine would be. Giving them my upmost attention. Keeping them active and making sure they are well feed and taken care of. Being alert on essential needs they might have as well as making sure they are loved and adored.
About: Hi! I’m Hannah, and I absolutely love pets of all kinds. I’ve grown up with dogs my whole life and have cared for three of my own. I’ve also provided dog-sitting and cat-sitting over the years, which has given me a strong understanding of different personalities, routines, and care needs. I treat every pet like family and focus on creating a fun, safe, and loving environment. Pet care fits naturally into my daily routine because I prioritize giving each pet consistent attention, exercise, and companionship throughout the day. A typical day starts with morning potty breaks, fresh water, and a walk or play session to get their energy out. Throughout the day, I provide regular check-ins, feeding on schedule, enrichment activities, and lots of love. I stay flexible so I can match your pet’s normal routine as closely as possible. I follow whatever routine the owner prefers to make your pet feel comfortable and at home. I can take dogs on walks or runs, provide fresh water, give meals on schedule, and spend quality time playing or cuddling whatever your pet needs! Safety, clear communication, and trust are my top priorities.
“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!”
“Jessica has been fantastic during drop-in visits for our dog Buddy! It was clear the second she walked in our home that she knows and loves dogs. Buddy was instantly comfortable with her thanks to her warm and welcoming demeanor. Knowing Buddy has someone that we can trust to drop-in while we are at work is very comforting. Highly recommend Jessica!!”
About: I've had dogs off and on my entire life but it wasn't until we adopted our baby girl Coco that I really fell in love. We had 13.5 wonderful years with her, then after she passed we decided to foster dogs in her honor and have been doing this since Sept. 2020 with several local organizations. We have fostered 25 dogs and have sat 26 dogs to date, including puppies, senior dogs, and dogs with behavioral and medical special needs. Our pricing reflects the peace of mind of knowing that your pet is well cared for and part of our family during their stay with us. Or for in house sitting, we are mature, reliable and trustworthy and treat your home like our own. We look forward to hearing from you! My husband and I are retired so we are very flexible in our schedule and decided we want to do something meaningful and enjoyable in our retirement. We have a large 1.5 acre lot with a pond on property. It is very serene and peaceful here. Our yard is only partially fenced so we keep the dogs on leash when walking outside. We make frequent potty breaks and like to take dogs for walks in the woods behind our house. They dogs usually sleep on a bed on the floor in our bedroom but will be crated if we have to leave the house for their own safety.
The median cost per visit for dog sitting in Chesterland is $20
Dog 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?
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 dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for dog sitting - Chesterland
Select a filter and find qualifying sitters offering dog sitting.Sitters in Chesterland average 6 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 August 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 August 2026, there are 2,180 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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