Dog Boarding Chestertown
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 23 pet parents in Chestertown have booked dog boarding
Chestertown, 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.
“Michelle was awesome. She sent photos every day and answered any questions I had. Zoey was happy and healthy when I picked her up. It was Zoey's first three-night stay away from home and it went very well!”
“We are very pleased with the care Pamela provides for our dog! She really takes great care to make our dog feel comfortable. She has a great fenced yard where our dog can run around and explore. Pamela also keeps us posted on our dog’s activities with daily pictures! We wholeheartedly recommend Pamela!”
“Goose had a wonderful stay with Jeren and I am so grateful for the clear communication and attention to her needs. She clearly knows a lot about dogs and provided excellent care.”
“Thomas was fantastic. We got updates and photos of our babies everyday. He was super responsive. Our babies played, had fun, and were happy. We definitely will be booking again.”
“As a first time user of Rover and first time search for a cat sitter, Elena definitely set the standard. From the first contact, Elena was incredibly responsive, very kind, and extremely welcoming of my babies. Elena and her children took such good care of my babies, as they allowed them space to adjust while being open to their affection as they warmed up. I had peace of mind that my babies were in good hands as she invited them into her home with open arms. When I picked Pocket and Rocket up, they were so soft from freshly brushed hair and calmer to get back into the car. I would absolutely recommend Elena to take care of your cats, as they will get plenty of cuddles, play time, and freedom to explore their new space. Thank you, Elena and kids!!”
“Barb was fantastic! We chose her because of her experience with dogs of all ages, especially older pups. Although our pup was a bit nervous, she seemed to settle in well and made herself at home. Really appreciated the updates and pics to let us know all was good.”
“Another amazing stay with Danielle! This is the second time Coco has stayed with her for an extended visit, and once again, we couldn’t be happier. It truly feels like a doggy vacation paradise for her. We know she is so well cared for, and we’ll absolutely be back again.”
“Ceil took care of my dog for a few overnights and I could not be more happy with the care he gave. From the time I dropped him over I knew right away my dog was in good hands. He kept me updated with pictures and videos which was very warming. If there were 10 stars I woukd of gave all 10”
“Jessica was awesome. She took great care of my baby Paris. She kept in contact with this nervous dog mom and made me feel at ease. Will definitely book with her again.”
“As always, Trixie came home tired and, most importantly, happy. Jenn and her husband do a fabulous job welcoming pups into their dog proof home. I also really appreciate the pickup/drop-off amenity. Will definitely use again”
“Jasmine was wonderful! She kept both of my dogs over a long weekend and they had so much fun. She sent daily pictures and videos and she was always in contact with me. I will definitely use her again.”
“Jen immediately put us at ease. Her positive energy and love of dogs came through at our very first meeting. She regularly sent us notes and pics of our dogs, which we really appreciated. Thank you Jen! We will definitely call again if we need a sitter!!”
“Becca did an awesome job watching Bodie while we were away. She was flexible, communicated well, and took great care of him. We really appreciated the updates and knowing he was in good hands. We’d definitely book with her again and highly recommend her to others.”
“Meagan, Chris, and pups, Butter, and Lucy took great care of Ozzie. Ozzie does not always warm up to strangers immediately but felt at home with them burrowing under their blankets and sleeping in their pup beds. They provided daily report of Ozzie antics and photos keeping me posted. Meagan really loved Ozzie and animals in general, and adjust to them easily. It was evident Ozzie enjoyed his staycation. We will definitely board Ozzie at their place in the future.”
“Chrissy was awesome. This was my first experience using Rover in Baltimore and couldn’t have asked for a better sitter. Communicated often, sent pictures, periodic updates and can tell Bear loved hanging with Dublin. Thank you so much again for everything and will definitely be my #1 go to ?”
“Steph couldn’t have been any more perfect for our dog, Remy! It was the first time we left a pet with a non-family member but I felt completely comfortable. Steph even has a doggie-sofa in her living area. I could tell from our first meet and greet that she was in tune with dog behavior. Her dogs are the sweetest hosts too! When we picked up Remy, I could just tell that she had a wonderful weekend. I really appreciate having a reliable, loving place to take Remy when needed.”
“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! 🐾”
“April is just amazing! She sends wonderful pictures with updates on how Yani is doing. She goes hiking and plays with Yani and make sure that she is really well cared for!”
“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!”
The median cost per night for dog boarding in Chestertown 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?
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 - Chestertown
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chestertown average 12 repeat dog boarding clients
FAQs for Dog Boarding - Chestertown
Frequently asked questions about Rover
The average cost of Dog Boarding in Chestertown is $40 per night as of October 2026. Most bookings cost between $25 and $71 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 1,490 sitters on Rover offering Dog Boarding across Chestertown. Enter your ZIP code to see which available sitters are closest to your home.
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 Chestertown 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 Chestertown home-away-from-home, 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 Chestertown.
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.
You and your Chestertown 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 , 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 .
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.
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