Dog Boarding Chesterville
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Chesterville, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Where do I start!? This was our first time going away and having to leave our Megan! She’s an elder fur baby and we couldn’t think of anyone who would properly take care of her. We turned to rover and it may sound strange but when I saw Barbra picture I knew she would be perfect! She sent pictures, and updates constantly! Our Megan looked so happy and taken care of! I am so pleased with her service and I will definitely be using Barbra in the future! Thanks a MILLION Barbra we appreciate you more than you know!”
“We were looking for someone to care for our Luna who would treat her like one of their own and keep her safe while we were away on vacation, and we found that person in Brittany. Her love for animals of all kinds and sizes is obvious and we are so grateful to have found a place like Safe Hayven Fields. The property is a perfect getaway with a large fenced in yard for running and playing, and the pool for pups that like to swim. Brittany is such a great caretaker, sending us daily photos and updates, even going above and beyond to replace Luna's bed when another pup made a hole in hers! We will be back and look forward to having Luna spend more time on the farm 💜”
“Finn had a great time staying with Tarina! She helped him up and down stairs and snuggled with him when he was scared of storms. She took such good care of him and I had peace of mind when I was away knowing he was in great hands. I am grateful we found her!”
“Pamela was wonderful with our boy Vito, she took care of him like he was her own. We got tons of pictures, she took him for walks, Also he got to run around in her fenced yard, and she followed his schedule for foods and medicines. I would use pam again for sure when we need a sitter for him. Thanks Pam!”
“I absolutely loved Paris. From the initial inquiry until I picked up my spoiled baby, Paris was nice, professional, informative and accommodating. She sent plenty of pics of my girl and was very easy to get in touch with during her stay. I will definitely be using Paris in the future to care for my baby!”
“It is so nice to know your dog is being cared for, Yvonne and Joseph has everything in place to keep our dog safe. promise to not leave her alone, and sent us updates. We could not have asked for anything more. We also appreciated the late pick up that they accommodated. Thank s again!”
“Daisy fit right in with the family! It was good to know that she got to hang with the kids and snuggle on the couch just like she does at home. The family did a great job communicating and being flexible about drop of and pick up. We will be booking again!”
“We were very pleased with our experience with Lindsay! As first time ROVER customers, she graciously addressed all of our questions and made it a seamless process. Our dog absolutely loved her time there with new playmates. She seemed comfortable and content and was obviously well cared for. We would not hesitate to book with Lindsay in the future and we highly recommend her as a ROVER care provider.”
“Alexandra is AMAZING! She has a very clean home and fenced in outdoor space for dogs to run and play! She accommodated our changing plans by taking Remmy a day early. She was so easy & kind to work with and I will book her every time we use Rover! She communicated daily and sent several pictures during Remmy’s stay! I had 100% peace of mind while I was away that my dog was extremely well cared for and loved!”
“We had such a great experience! She took amazing care of Cookie and made us feel completely comfortable while we were away. She kept us updated, sent us pictures, and Cookie looked so happy and comfortable with her. 🥹❤️ It was clear that she treated Cookie like her own. We’re so grateful for the care and attention she gave her, and we would absolutely book with her again. Highly recommend! 🐾”
“Brooke watched our boy Doc for a week while we went on vacation. It was super convenient since she only lives two miles from us! We are grateful she was able and willing to board him in her home. Brooke is very nice, friendly, and we will definitely book with her again if needed!”
“Samantha was great! She sent photos to us and took amazing care of our two pups. She was also very flexible when our needs changed. Will definitely use her services again in the future.”
“Our boy Bentley had an absolute blast at Jilesa’s farm. He is still wore out from his vacation there! This was our first time using Rover and Jilesa was very kind to allow us to do a meet beforehand. My kids loved visiting and loving on her animals. She is an absolute animal lover and a master of her craft. I was able to check in throughout the week and see lots of pictures of my boy living his best life. My family and Bentley can’t wait to come back again! Thank you so much Jilesa for loving on our boy this week and keeping him safe:)”
“We had such a wonderful experience with our puppy sitter! She took amazing care of our two puppies while we were out of town and treated them like they were her own. She kept us updated, and it gave us so much peace of mind knowing they were in such loving hands. When we picked them up, they were happy, healthy, and clearly well cared for. She even mentioned how sweet and cuddly they were, which made us smile! We are so grateful for the love and attention she gave Benji and Stormi. We highly recommend her to anyone looking for someone trustworthy, caring, and dependable to watch their pets. Thank you again for taking such great care of our babies!”
About: We are a family with a 13 year old girl, 9 year old girl, 2 sweet cats, 2 hamsters and a yorkie! All our animals are vaccinated and not aggressive. Our girls are animal lovers and have been caring for pets since they could walk! We are used to prioritizing pet needs and are home throughout most days and could likely accommodate the most unique needs - without judgment! We have 3 adults in the home and there is rarely no one home at all. One adult works part time and one works from home. Kids have school and sports but as a family, we are used to prioritizing pets’ needs regardless of the daily schedule. We live in a beautiful neighborhood with nearby parks for walks and have a small back yard that is not fenced in. We have space for a crate indoors if needed, but also can provide lots of snuggles.
The median cost per night for dog boarding in Chesterville is $50
Dog parents share their Rover experiences - Chesterville
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 dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
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 dog boarding - Chesterville
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chesterville average 10 repeat dog boarding clients
FAQs for Dog Boarding - Chesterville
Frequently asked questions about Rover
As of November 2026, there are 1,012 sitters on Rover offering Dog Boarding across Chesterville. Enter your ZIP code to see which available sitters are closest to your home.
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.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
95% of sitters in Chesterville can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chesterville home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Chesterville.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Chesterville. On Rover:
- 90% of sitters can help with special care needs
- 96% 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.
You and your Chesterville sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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