Dog Boarding Chestertown
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 21 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.
“We had another wonderful experience with Gisel and her family. Toby and Milo were so happy to see her again, which says everything about the comfort and trust they feel with her. We truly appreciate the attention, updates, and the warm environment she provides. Thank you again for taking such great care of our babies. We’re so grateful!”
“Amazing from the meet and greet and throughout the entire weekend stay. Michelle was very very communicative of what was going on with my pup. Would totally book again!”
“Sadie did really well staying with Jacob and Megan – with getting older, she has some anxiety when she’s not at home and can be a little 'stubborn'. They were very accommodating and I appreciated the extra effort. I would definitely use them again to watch Sadie!”
“Tarina is always there whenever we need a place for our dogs. She is trustworthy, loving and always takes the best care of them. My dog is always exhausted when coming home from a stay because he has so much fun! So happy we have her whenever needed.”
“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!”
“Our dog sitting experience with Shuling was wonderful. Lucky, our 4-year old mini goldendoodle, and his 2-year old beagle cousin looked like they were having a great time running around outside then relaxing inside. Shuling sent us lots of pictures. We would definitely contact her again if we need dog sitting coverage the next time we are in Annapolis.”
“Pat & Bee are absolutely amazing. They went above and beyond any of our expectations. They send frequent updates with photos and videos. They are kind and loving and extremely prepared. We absolutely loved our experience with them and will us them for ANY future boarding needs. Thank you both so much for taking such good care of Ellie!!”
“Paris took great care of our 14 year old doggie - Rosco. She provided us with feedback and pictures every day. Rosco is a nervous/anxious dog. But, Rosco seemed relaxed in Paris' care and was happy when we picked him up. I will use Paris again when the need arises.”
“Ran into a need of a last minute sitter for a night, had quick response time of being able to watch my dog. When I picked her up the next morning she was a happy and sleepy girl!”
“Lucky had a great time with Max and Thomas. He enjoyed playing in the backyard and all the pets. Thank you and I'll definitely rebook again. I appreciate the prompt replies to my texts.”
“Wow, I can't say enough about how well Katelyn cared for and accommodated our dog Oscar. He was nervous at first but quickly adapted and thrived - thank you Soooo Much, 6 stars out of 5! Definitely a keeper!!”
“Lindsay is absolutely amazing! She treated our furr baby like her own. We are so grateful to have came across her. We will definitely be booking with her in the future. ??”
“Jeren was absolutely incredible! I had to make several changes within a few days before our booking and she was so quick to respond and accommodate. Jeren constantly kept us updated with pictures and videos of our baby throughout his visit. We are so grateful and will definitely be booking again!”
“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.”
“Our 9 month old lab enjoyed his first time away from us at Jenn’s house. We did a meet and greet beforehand and received updates throughout his stay which put us at ease! We also loved the papers that came home that gave daily details about his stay. We will definitely book again!”
“We had the absolute pleasure of having Brittany watch our Toby for extended stay while we were on vacation. From the first meet and greet, we were certain we made the right choice as it is apparent Brittany genuinely loves animals and pet sitting. Her beautiful home and farm is such a welcoming place for animals of all kinds and our dog even used the pool for swimming. We really enjoyed the daily pictures and updates from Brittany to put our minds at ease. She even gave our dog a bath at the end. Highly recommend Brittany if you are looking for a loving pet sitter!”
“Sherman loved his time with Jill and Chad and family!!! We could tell that he got so much attention and affection. Sherman can't wait for his summer vacation in July!”
“Jessica was very accommodating throughout the process. She even agreed to having our furbabies meet before the stay so I was comfortable with their likeness to each other. She was also very accommodating and get me updated on my little Oliver was doing. Would definitely book again with Jessica :)”
“Theresa was absolutely amazing! She communicated very well & cash loved her. She has an amazing home & cash loved exploring her yard. She was patient & very knowledgeable about all types of dogs. I was definitely recommend & I'll be booking again soon.”
“Carlie was amazing with our puppy Sadie. It was our first time leaving her with anyone and it went so well. Lots of love to our sweet puppy and she was happy all day. Carly shared lots of pics as well. Highly recommend!”
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.
Meet local sitters who will treat your dogs like family
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 Boarding - Chestertown
Frequently asked questions about Rover
The average cost for Dog Boarding in Chestertown on Rover is $36.07 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding 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 Boarding. For more information on service fees, click here .
As of September 2026, there are 1,487 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 rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
93% of Chestertown sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Chestertown landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chestertown 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 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 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.
Connect anywhere with the Rover app
