Dog Boarding Chestertown
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 18 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.
“Gisel and her family were great with my special needs dog. I could not be more grateful for the love and care. I hope to that this family will be my go to. My little guy was happy to see me but was sad and kept wandering around because I think he was looking for the kids.”
“Danielle took great care of my dog while I was away! Sadie was happy and well cared for when I picked her up. Danielle was responsive and sent me regular updates so I knew Sadie was happy and safe. I highly recommend Danielle!!”
“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.”
“Shuling was amazing! She sent us pictures and videos the whole time and made it easier to be apart from our pup. Bailey had a great time playing with the host’s dog and family. Honestly, it looked like a summer camp for the doggies :) 100% recommend her and will use her services again. Jake and Ana”
“Super amazing people .They have had Thor twice and will probably continue to they take amazing care of him and treat him like there own . We love the fenced in yard and the walks .”
“Theresa has been caring for our dog for years, and she has always been absolutely wonderful. She is incredibly sweet and kind, and our dog truly loves her. She will forever be our go-to person. Theresa has even stepped in to watch our dog at the very last moment without hesitation. If you’re looking for someone with a truly kind heart, stop right here and give her a chance. We love her—and so does our little dog.” 🐾💖”
“Sampson had a great stay! I received updates & pictures while he was in her care. He was exhausted when he arrived back home, which means he had a great time. Thankful for the care he received, and will definitely be using again.”
“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.”
“Cecil was amazing he took great care of my dog. Plus my dog got to socialize with other dogs. Which can be difficult because he's a pittie. I'd highly recommend him if you need dog boarding”
“⭐️⭐️⭐️⭐️⭐️ I don’t know how to explain this except: Jess is basically Dodger’s second family now. ⭐️⭐️⭐️⭐️⭐️ If you’re looking for the type of sitter who treats your dog like FAMILY…like actual family…Jess is the one. I honestly don’t think Dodger realized he was being “boarded.” He thought he was on vacation with his new cousins, new uncles, and his new favorite person on earth (Dan 😆). From the minute we dropped him off, Jess was so reassuring and kind. She sent constant updates, pictures, and little stories that made my heart feel so much better. And not just “here’s your dog existing” pictures…NO. We’re talking: *Dodger cuddling her husband like they’ve been best buds for 10 years *Dodger snuggled up with her youngest like they were watching Saturday morning cartoons *Dodger and Tanner acting like long-lost brothers reunited *Dodger eating, relaxing, wagging his tail like a helicopter blade *Dodger getting a whole spa bath after rolling in the yard mud 😭💀 He even chewed through a Kong, which honestly deserves its own award. I warned her he was a super chewer, but I don’t think ANYONE was ready for him to destroy the “indestructible” toy. She just laughed and sent pictures like, “Welp, he’s having the time of his life.” 😂 The whole time she made sure I felt comfortable…even when my baby stole my phone and I panicked thinking I missed messages 😅 She was patient, flexible, and genuinely cared about him AND about us. Dodger came home happy, clean, tired, and FULL of love. His tail literally didn’t stop wagging the entire stay. And I’m pretty sure he thinks Jess’s house is his second home now…which I’m honestly fine with, because I know he’s safe and adored there. Jess and her whole family are wonderful, warm people. They treated Dodger like he belonged with them, and that’s all a dog mom could ever want. We will definitely be booking again (unless Dan steals him permanently 😂). Thank you, Jess, for loving our boy so well. He misses you all already! ❤️🐾 P.s thank you for being so accommodating and helpful with his bath, I loved getting to pick him up early and snuggle him with us the moment he came home🥹💕”
“Pat & Bee were phenomenal pet sitters! I got frequent photo updates on the status of my pup. They even helped her out when she is a super picky eater. I would highly recommend them and would definitely use them again!”
“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 :)”
“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.”
“Barbra was an excellent host to my little Millie. She welcomed her into her home and treated her like a very special member of the family. Millie received excellent care and plenty of attention!”
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
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Popular requests near you
Select a filter and find qualifying Chestertown sitters!Sitters in Chestertown average 12 repeat dog boarding clients
FAQs for Dog Boarding - Chestertown
Frequently asked questions about Rover
The average cost for Dog Boarding in Chestertown on Rover is $30 per night (as of July 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 July 2026, there are 1,478 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.
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