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.
“I can’t say enough about Gisel and her family that gave us a warm welcome the moment we connected. At our meet and greet, I knew she was the one to host our #furbaby Cody. Even her children were loving towards him. They are a wonderful family and far exceeded our expectations of caring for our Cody with pics and videos the whole seven days. Our neighbor uses her as well for their Yorkie and are very pleased with the care they’ve received. The bonus for us, she’s a stay at home mom and Cody was not left alone all day. She has small dogs as well and he was able to meet new friends. This was our first time leaving Cody without family and Gisel eased all of my anxiety because of her love for animals. We’ll be using her again soon.😊”
“Working with Megan and Jacob was a pleasure! Cooper looked like he was having a wonderful time in all the pictures they sent. Dunkin’ and the other buddies were great companions while he was there, too.”
“Our puppy came home happy and healthy, and perhaps even a bit more well mannered after boarding with Michelle! His wonderful behavior after staying with Michelle was an absolute contrast from after the kennel. He was so nervous and barked a lot after boarding at the kennel.”
“Another wonderful stay with Danielle! Coco is always happy and so well cared for when she stays with her. Danielle continues to be our go-to whenever we need a home away from home for Coco!”
“Carlie and her family could not have been more loving and attentive. Arlo probably wanted to live there forever. She was incredibly kind about a mistake I made on pick up time.”
“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!”
“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.”
“my pups first overnight stay with Paris went perfectly! he got lots of attention and love and was comfy through the night. all the things i could ask for when he’s in someone else's care. truly appreciate Paris for treating my pup as if he was her own.”
“Another great stay for Cocoa! He loves going over here & Ms.Theresa is always so kind in updating and sending over pics. Will use her again and again and again!”
“My dog loved his stay here! He came back tired and happy. I got lots of pictures of a very happy dog, I can tell he got a lot of love from their whole family and lots of fun playtime.”
“If I could give 10 stars, I would. Katelyn is very kind and helpful, in addition to being understanding of HoneyBee's blindness and separation Anxiety. I appreciate all the pictures and videos of my pup while I was away, and especially all the attention given to my pup as well as flexibility of scheduling. Would highly recommend to anyone in the area.”
“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!!”
“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 .”
“Jessica was easy to work with, and took good care of my girl. I received pictures, she quickly responded & my dog was happy when she was picked up. She must have had a good time!”
“Jeren did an amazing job with my dog! She was even flexible with my pick up time when my flight got delayed. Would definitely recommend if your dog likes other dogs and is very shy like mine”
“When I was searching for an sitter for my labradoodle I didn’t expect to find such an great family to care for my dog , Jill and Chad are the best they kept me updated on how Tucker was doing , with pictures and video the entire family is great 😊”
“Leia was living her best life like she was at a pet resort. Marliez treated Leia like her own with great care and attention, making her feel right at home. I received regular updates and photos, which gave me complete peace of mind! I’d definitely rebook with Marliez. Leia has 3 new friends and thinks she’s the boss of cats now!!”
“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.”
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
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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 August 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 August 2026, there are 1,465 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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