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.
“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 💜”
“My dog Barkley was so well cared for by Megan & Jacob! I could tell he felt comfortable right from the start, and I appreciated their great communication before and during Barkley’s time with them.”
“Outstanding dog sitter! My dog had a blast and Pamela C. was wonderful about documenting it through photos and sharing. Excellent communication and clearly a wonderful dog person. Highly recommend!”
“Paris is amazing with our sweetheart! She takes excellent care of our baby & sends her home happy! We were worry free while we were away as we knew our Paige was in great hands.”
“Jill & Tommy were great! Milly had a great time playing with 5 new friends and we were kept updated with texts & pictures daily. Today she seems lonely with just me on a rainy Monday. Paul & Marybeth”
“McDuff stayed with Karen for 9 days. We received regular updates and reports on how he was adjusting to his surroundings. While we were gone, Karen sent photos and video showing McDuff’s interactions with other dogs at her home. She bathed him as he got really muddy while he stayed with her. When we picked him up, he was happy and content—glad to see us, but also he was still full of play with his new friends. Highly recommend!”
“Everything went well with my dog's overnight stay. She got her walks and Sandra communicated with me throughout her stay with photos. Much appreciated Sandra! Hope to use your services again. Lisa H.”
“Yvonne and her husband granted me an amazing experience of boarding my dog (Freda). It all began with a last minute trip, which required me to board Freda within 48 hours. I sent Yvonne a request based on her location and availability for the days I required. This turned into a blessing. She replied almost immediately. She offered to host Freda as long as as our initial meeting between Freda and her own dog (Quincy) went well. When I first arrived Yvonne and her husband were so welcoming. We discussed our pets and introduced ourselves - it felt more than just business of boarding my dog. This experience was different. This experience was exceptional. They showed me around the area of their home where Freda would eat and sleep. They also showed me around their beautiful fenced in yard where she could run comfortably. They also stated they only host one pet at a time and never leave the dog unattended. This put a lot of my thoughts at ease. Throughout my trip Yvonne sent me pictures and provided me updates and once again worked well with my return schedule to pick up Freda. I will definitely be using Yvonne again if she’s available as she was a wonderful host to Freda and I. Thank you.”
“Justin&stephanie were great! I booked last minute and they were able to take my dog. The whole time they’ve communicated and updated me quickly and right away, sent me pictures, played with him, took him for walks and made him feel so much at home!! My dog was sad about leaving. Book with them for a safe and good experience for your fur babies!”
“Nikkita was excellent. She responds to texts quickly and kept me updated on possible problems. She sent me frequent photos as well. Winston seemed to like her and her family! Would definitely recommend.”
“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!”
“Lindsey is an amazing sitter!! She shows a lot of love to Chico and he loves her back. Chico came back to us clean, well fed and with no issues. Lindsey's children are very fond of him too. And I appreciate the fact that she sends me pictures of him at play with his furry friends every day. That keeps me at peace to know he's having an enjoyable stay.”
About: I’ve have been a dog owner all throughout my life. I currently have a golden retriever that is three year old named Steve. I know level 1 and level 2 dog training techniques. And enjoy taking dogs for long walks to get their energy out. I live five minutes from my job and can come home if needed and never work weekends. My wife works from home 3 out of 5 week days. I have a large fenced in yard (.75 acres) and a dog friendly golden retriever named Steve. I have an extra crate available if your pet needs crating.
“Molly was great with my Kash,This was his first time with her and she was amazing with him caring playful and loving. Will definitely use her again.Thanks again Molly .”
“This was the first time we ever had the guys to leave our girl with anyone. The meet & greet went great the day before our scheduled drop off. Our baby took to Alessandra, her husband, and their female dog right away. She loves kids so I knew she would be comfortable with their kids. They sent daily updates along with pictures of Dior. They answered very quickly whenever we reached out. And Dior looked happy and comfortable in the pictures. We will leave our baby with them anytime we need a sitter. They are a great family, and they took care of our baby like she was their own.”
“Brooke was amazing and took wonderful care of Monet. She was great with communication and keeping us updated with how Monet was doing with her. Monet came home very happy! Thank you, Brooke!”
“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.”
“My puppy stayed with Sharon for 3 days and I’m so lucky to have found her. I live 40 minutes away but she’s worth it. Her dog, Belle, is such a sweetie. The place is clean and the backyard as well. My dog is a little bit mischievous but Sharon handled him very well and he was very happy there. I highly recommend Sharon for everyone who wants to board their dogs, she loves dogs and will go extra miles to take of your dog. You will have no worries leaving your dogs with her.”
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.
Connect anywhere with the Rover app
