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 took great care of Ace for an entire week. She communicated daily with chats, photos and videos of my little fur baby. She really treated him like her own and I definitely am coming back to her again. I HIGHLY recommend her!”
“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!”
“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.”
“Lindsay was amazing! She sent photos everyday, loved io Pepper while my daughter and I were away, and was always quick to respond if I had a question. Her home was lovely and Pepper enjoyed Lindsay’s backyard and her sweet dog, Coco!”
“What a delightful time Ginger had, with this lovely family. Carlie was attentive, flexible, and like a second home while I was away. I will definitely be returning.”
“Good morning our dear Rover family. We'd like to express our deepest gratitude and appreciation for Theresa. Each expression of love every picture made our hearts smile knowing Cheanna was well taken care of. Theresa's service exceed our expectations. We are happy to say we will be using her caring help in the future 😀. Words cannot say how safe we feel using Rover. Thanks a 1000 times.”
“Katelyn was really excellent and accommodating for our puppy’s needs. She was vigilant about potty time and gave us multiple updates while we were away for a wedding. She was welcoming and helped us feel secure, especially for one of our first times using this type of service. Definitely recommend!”
“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!”
“After multiple sitters canceling, I found Rover and Danielle, who was happy to watch Remi at the last minute. The universe knew what it was doing, as Danielle and Remi bonded the moment they met. As he spent the majority of his life as a puppy mill papa, Remi can be challenging. As a teacher and a mom, Danielle had the skills and patience to work with him. She kept us updated throughout the weekend and it was easy to see the Remi was happy and content. I’m fairly certain Remi didn’t want to come home !! We couldn’t be happier to have found someone to care for our dog like one of her own! Next time we need somebody to care for our pup, she will absolutely be our first call!”
“Shuling was fantastic! I was very nervous to have my pup Miso puppy sat for the first time, but I needed a sitter for the holiday weekend, with very short notice. Shuling said yes immediately, and allowed me to come and meet her and her sweet pup Bear that same day. She really put me at ease. She kept Miso for 3 nights and sent several photos twice per day. I never had to worry at all. I can’t thank you enough, Shuling! Miso would love to come and hang out with you again sometime soon!”
“The level of detail and care that Patrick & Bahiya is above my expectations. This is the second time boarding my dog with them due to their trust and professionalism.”
“⭐️⭐️⭐️⭐️⭐️ 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🥹💕”
“Can’t say enough great things about how well Briana and Isaiah care for my pup! We love them and fully trust them to care for her when we are away! I never stress if my dog is okay and she’s always happy to see them and happy and healthy when we get her back! You’ll have no regrets leaving your fur babies with them!”
“Just had our 2nd stay with Barbra and it was fantastic! She takes such great care of our dog and we will be using her anytime we can. I think our dog was very sad to leave with all the fun he had playing and roaming her huge yard. Highly recommend her services!!!”
“Best dog boarding experience ever! Happy dog, happy pet parents! How can you beat a family of 4 totally focused on your pet. Our 10 yr old was thrilled to find there were 2 boys to keep our Daisy cuddled and loved. Jill and Chad are great - pic updates, great communication. We WILL be using them whenever we travel. This was like leaving our dog with best friends. Thank you so very much. Your family is so appreciated!”
“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”
“Molly was able to step in on a last minute request for our Astro, and she was wonderful. She kept me updated with Astro’s daily activities. She is kind and Astro liked her very much. I will use Molly again for my pet sitter needs.”
“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.”
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
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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 $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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