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.
“Jeren was able to watch our new pup on short notice and did a great job. She sent daily pictures and descriptive updates. Our pup looked like she had a blast! Additionally, Jeren had no issues giving ear meds and was patient with our pup's shy nature. When we need a petsitter again, we'll be contacting Jeren first!”
“Michelle took care of my dog, Sophie, while I was visiting my family in Boston for four days, and she was great! She sent me updates and pictures daily and gave me prompt responses when I asked her questions. Sophie had a great time with her new friends, Tanner and Rosie! I appreciate Michelle sleeping with Sophie and giving her a lot of love while I was out of town. I highly recommended her!!”
“Great meet and greet and first time stay for my dog. The two other dogs were great with mine and were quick to become friends. I enjoy the large back yard which allowed my dog to wear himself out while playing with friends. Paris did an amazing job of keeping me posted with pictures and text updates. I highly recommend Paris to care for your fur babies.”
“Brittany’s home is an oasis for dogs. Our girls loved chilling out in their big fenced in yard which they could sunbath or hide out under the shade trees especially the beautifully willow. Brittany is very responsive and without a doubt a true dog and animal lover. Trust that this would be a great place for your furry friends.”
“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!”
“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!”
“Lindsay provided great care for our dog Daisy while we were away on vacation. We enjoyed all the photos of Daisy with the family and Lindsay's dog Coco playing in the large fenced in back yard. I would definitely recommend and will be booking again in the future.”
“First time boarding my puppy and had to book last minute. Briana & Isaiah responded quickly and made the experience easy and stress free. I could tell quickly that was Benny in great hands! When I picked him up he had the best send off, they truly care. Will definitely book again.”
“Jenn and her husband were great! Milo has a lot of separation anxiety, and they handled it with ease. They were very communicative and sent plenty of pictures. Would highly recommend!”
“This was my first time using Rover. I read all of the reviews for Shuling and was very impressed with what previous customers had to say. I requested her services and she accepted, even though it was deemed a last minute request. She was very communicative, responded quickly to my questions and made booking with her easy. Upon drop off, she was waiting for us outside and greeted us warmly. Throughout Loki's stay, she provided multiple pictures of him daily. She put our hearts and minds at ease knowing he was in good hands. I had a request to extend his stay a few more days and she didn't hesitate to accept. Made the change to the dates easy. Upon picking him up, she was waiting outside with him and he was happy and healthy! I will definitely use Shuling 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!!”
“Hester was absolutely wonderful! Sent us updates on our boy while we were out of the country and shared about all the fun he was having. Would definitely rebook and recommend!!”
“I’m so glad we found Patrick and Bahiya on Rover to take care of our dog. My Loki can be a little “extra” but everything worked out so great and it was wonderful to be able to enjoy our vacation and know he was so taken care of. I can’t thank you enough for the daily updates seeing him so well taken care of.”
“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!”
“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!”
“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.”
“Another stay with Carlie and we cannot recommend her enough! We always have such peace of mind with her daily updates and photos and knowing that our pup, Indi, is safe and having fun. Indi gets her own vacation when she stays here and we love knowing that our she gets to enjoy herself, too! Between Carlie's loving and kind family, the huge bonus yard, and Carlie's attention and ability to continue medicine (she even notices any behavioral changes!), we just know we've made the right choice. Do yourself a favor, and get on her schedule for your pup sitting needs! :)”
“Barbara is so great with animals and does a great job making them feel at home. Our dog had a great time and enjoyed her visit with the family. I loved all the photos to see how our dog was doing throughout the day. Wonderful job!”
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 Dog Boarding - Chestertown
Frequently asked questions about Rover
The average cost of Dog Boarding in Chestertown on Rover is $40 per night as of October 2026. Most bookings cost between $25 and $71 per night. 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 1,502 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.
93% 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, 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.
<b>Tip:</b> 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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