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

Chesterville, 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.
“Busara was an incredible dog sitter! From the moment she came for the meet and greet, I was impressed. My dog was calm and took to her immediately, which gave me so much peace of mind. She even took notes about his care, showing how attentive and thorough she is. After the meet and greet, she sent a detailed care summary and promptly accepted the booking. Throughout our trip, she communicated amazingly, sending multiple updates and photos of our baby every day through out the day. It made being away so much easier knowing he was happy and well cared for. When we returned home, everything was in perfect condition. She brought in our mail, watered our plants, and most importantly, our dog was happy, relaxed, and clearly well loved. I would absolutely recommend Busara to anyone looking for a trustworthy, caring, and professional pet sitter. We will definitely be booking with her again the next time our family travels!”

“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”

“Madison did an excellent job taking care of our 12 year old St.Bernard/Staffy mix, Charm! Madison was very capable, patient, kind and moved at Charm’s pace, making Charm very comfortable with her. Madison provided great communication during her service so we were worry-free during our trip! Will rebook with Madison in the future! 😊”

“Rebecca did an excellent job staying at our home with Pippin! She was really prepared with questions to help the weekend good smoothly and to understand his needs. She was very responsive to messages and sent detailed updates and pics. Our pup had a great time!”

About: I work professionally in dog daycare as a Team Lead, where I care for dogs of all sizes, breeds, ages, and personalities. I’m experienced with group play, individual care, feeding routines, senior dogs, puppies, basic training and behavior management. I’m comfortable reading canine body language and adapting my care to each dog’s individual needs. I also have experience with large breeds and higher-energy dogs, and I treat every pet in my care like one of my own. Pet care is already a big part of my daily routine through my work in dog daycare. Outside of work, I’m available for drop-ins, walks, and other pet care services depending on the day. I’m happy to work with your pet’s usual routine and provide consistent, attentive care while you’re away. I always prioritize safety, comfort, and each pet’s individual needs. I pay close attention to body language, behavior, and stress signals, and I’m comfortable following detailed feeding, walking, medication, and care instructions. I believe in keeping pets on a familiar routine and giving them the space, enrichment, exercise, and affection that works best for them.
About: I have lots of compassion when it comes to animals, and I have years of experience working for cat/dog rescues as well as pet transports, I currently have a four day weekend at my current job and have way too much free time! I also have no problem with early mornings or late nights! I have two small dogs that I take for a couple walks a day, and I Help prepare their food which is home made and all natural. I also have a cat with urinary tract issues so I’m used to keeping their litter boxes spotless.

About: Welcome to Safe Hayven Fields At Safe Hayven Fields, we’ve created more than just a place for pets—we’ve created a peaceful sanctuary where every furry friend is treated like family. Nestled on our beautiful horse farm in lower Cecil County, our little slice of paradise offers breathtaking views, fresh country air, and plenty of room for adventure. Whether your pup loves splashing in the pool, running and playing in our safe, clean, and secure outdoor spaces, enjoying cozy snuggles inside, or taking a stroll to visit the horses, every day is filled with love, fun, and personalized care. We believe the most important thing we can give your pet is love. We care for each guest as if they were our own while always respecting and following every parent’s wishes, routines, and special instructions. Your pet’s happiness, comfort, and safety will always come first. Our hope is that Safe Hayven Fields becomes your pet’s home away from home—a place they’ll be excited to return to, with wagging tails and happy hearts every single visit. We can’t wait to welcome your family into ours. ❤️ My entire life revolves around my farm and caring for all of my animals. I am on the property 24/7 as this is my full time job. And luckily it’s my passion. We have a beautiful fenced in pasture with lots of space to run. We are in a very private and rural area. We also have a pool- only if parents are OK and the Pup chooses to take a dip! Your Pup will always be supervised. If there are restrictions we will always abide by them. We also have dog crates if needed or requested and a beautiful inside area as well. Basically your Pup is gonna have free range and feel a home away from home.
“Our dog has so much anxiety and Kathleen was amazing with him! He warmed up to her with her patience and it was a great weekend! She kept us updated and in turn we had a great time away, not worrying at all. She communicates well and quickly, she kept our house clean and in great condition. We would love to have her stay and take care of our dog again. Definitely recommend her to anyone else looking.”

About: Taken care of many of my neighbor’s, family’s, and other’s pets over the years. I’ve done overnight stays as well as drop ins and walks. I have pretty wide availability so just let me know what you need! I’m in a graduate program so I can do overnight stays & walks/drop ins. I’m pretty flexible so just let me know when you need me and we can likely make it work! I maintain a safe environment and closely follow instructions from the owner! I’ll always reach out if I’m unsure of something to make sure I can give your babies the best care!
“Krista did an amazing job! She was very friendly and our dog Molly did great with her. Krista was very attentive to Molly and was very respectful of our home. She kept us updated and sent pictures! We will definitely be having Krista watch our fur baby again! Thank you Krista ❤️”


About: Ive taken care of many animals my whole life ive owned a few dogs one of which was born deaf and i had one who went blind at an early age so i know how to handle special need dogs and other pets and have been dog-sitting and cat-sitting for many people since I was 12, I love all animals and will take care of them as if they were my own. I am experienced with young puppies and senior dogs. I am also experienced with dogs that suffer from separation anxiety. I am also very good at sending lots of pictures and daily updates of your fur babies! I am currently working part time at a med spa and I make my own schedule so I will have plenty of flexible time in my day to spend with your pets for whenever you need. I have 2 dogs of my own at home although I do not offer other pets to stay at my home due to having a sensitive senior dog of my own who was born deaf and is now partially blind. I will however be able to stay at your home with your fur babies and even do overnight and extended visits for however long you will need them to be watched. I also will clean up any mess your pets will make because I know how chaotic it may be so please leave out any cleaning supplies I may need.
About: About Me: I am a teacher, pet mom (to both dogs & cats!), and lover of all animals. I lead my life with empathy, which makes me an extremely patient and effective pet care provider. It is my mission to treat your babies with the same amount of love, respect, and compassion that I would hope somebody would give to my own. I believe that behavior management, if necessary, should always be rooted in consistency and positive redirections. My Experience: Beyond being a cat and dog mom, I have years of experience with long term cat and dog sitting. I am experienced and comfortable with any age of pet, from puppies/kittens to senior animals. I have some basic experience with training from my own pets. My Schedule: Until my summer ends, I am available almost daily. Once school starts, I am available on weekends and week day evenings. During these times, I can do check ins, feedings, walks, play times, or overnights. I am comfortable with week day overnights, if your pet is able to be alone during my typical 8 hour work day. I am a teacher. Until my summer ends, I am available almost daily. Once school starts I am available on weekends and week day evenings. During these times, I can do check ins, feedings, walks, play times, or overnights. I am comfortable with week day overnights, if your pet is able to be alone during my typical 8 hour work day. I am empathetic, nurturing, responsible, and consistent. At the end of the day, the thing that makes me most effective is my genuine love for animals. I care for and approach all animals as gently and lovingly as I do for my own. I am comfortable with many styles of pet care including crating, walking, outdoor and indoor play, anxiety management, and more. As a mom of an anxious rescue pup, I understand the importance of providing an animal a safe space. I make it my mission to help all pets feel comfortable and confident around me. I mold to your pet’s needs and personality, rather than making them bend to my own.
“Taylor is a huge help and Maxwell loves spending time with her! She is attentive and makes sure Maxwell is entertained and has someone to snuggle with during the day. 10/10 for sure!”


“Courtney was an amazing help with sitting Maxwell today. She was punctual, early in fact ;), followed all requests and most of all, made sure Maxwell was in good company. Communication was great and I felt confident that my little man would be in great care with her! We will be looking to have Courtney back in the future for sure. Thanks!”


“Nina was awesome, she was always on time when we met up, took care of Roo and the house the same way i would. House was just the way we left it. Roo definitely made a new best friend and we found out house sitter for the future, she sent us pics and updates on how things were going and she even sent pictures of the snakes. Lol. Couldn't go wrong booking with Nina if you need a house sitter, will definitely be using her in the future.”

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!
About: From caring for 10 senior dogs at a rescue, to bathing dogs that got sprayed by skunks, to training and taking dogs on their own outings to parks and nature hikes, you name it I’ve done it! Even flying with dogs! ✈️ I have experience with all breeds, ages, and like to keep pet parents informed with notes & pics. Growing up in farm country taught me to love and care for all animals, but dogs and cats are by far my favorite. I also have experience in administering medications to our furry friends. I left my career of being a nanny in CA to move to the east coast to marry my husband. That was 2019, and I’ve been boarding/caring for animals since then. I’m currently a stay-at-home wifey so the dogs get 100 percent of my attention when they are with us. We live in a 3 story townhouse with a small unfenced yard in front of our home, to a large grassy area on the side of our home, to a giant green grass patch directly behind us just out our back door. The neighborhood is VERY dog-friendly with lots of sidewalks and comes complete with a dog park in walking distance. Our home is dog-friendly meaning dogs are allowed on all furniture and we even have doggie steps for little pooches to get up on our bed if they wish. We also have a 2mile + walking path near us. So we have plenty of activity options. We even have Pluto cartoons for your pet to watch! Pets get 100 percent of my attention when they stay with us. Their comfort and safety is my priority as I do pet care full-time. Our home has no place that’s off limits to your pets. If they want to snuggle on our bed or relax on our couch or even be in our guest room - they are more than welcome wherever they are most comfortable. We even have a massive bean bag most animals love thinking it’s a giant dog bed 😂.
“Brigid was excellent!! She cared for my dog like he was her own. She gave him his meds on time and kept communicating with me while she was caring for him by sendings pics everyday! I would hire her again!! Thanks Brigid for taking care of my boy with love and caring for his needs!!”


About: I’ve fostered shelter dogs and taken care of small puppies from a young age. As a healthcare worker, I’m cpr certified, caring, compassionate and attentive. Book me for your furry friend! I work full time as a phlebotomist and have ample time on the weekends to dedicate to your pet. I will ensure they have a fun time on their walk. Growing up, I walked my family dog and ensured that he got his meals and walks. It gives me so much joy to meet clients’ dogs and take care of them as if they were my own.
About: When I was around 8 I started volunteering at a barn simply because I loved to be around animals. I was constantly walking my neighbors dogs and my own. I now work at a boarding facility where I take care of dogs and cats. I love it and enjoy nothing more than making sure your pets are happy and cared for when you are not able to be there all the time. My friends and neighbors often ask me to watch their pets when they are away. My family currently has 3 rescue dogs, a cat and 3 horses. I look forward to the opportunity of caring for your fur babies!! I am going into my freshman year of community college and love the opportunity to be able to do something that I love in my free time I currently have 3 dogs that get along really well with each other and other dogs. I pay very close attention to how dogs act around each other and their environment to ensure they are safe.
The median cost per night for house sitting in Chesterville is $50
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.
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. Search
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Popular requests for house sitting - Chesterville
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesterville average 4 repeat house sitting clients
FAQs for House Sitting - Chesterville
Frequently asked questions about Rover
As of September 2026, there are 1,542 sitters on Rover offering House Sitting across Chesterville. 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 Chesterville 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 Chesterville 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 Chesterville 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 Chesterville. On Rover:
- 95% of sitters can help with special care needs
- 99% 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.
