Dog Boarding Chesapeake City
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 135 pet parents in Chesapeake City have booked dog boarding
Chesapeake City, 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.
“Barbra is a wonderful pet sitter. She's always kind and understanding, always happy to accommodate our schedule and takes excellent care of Charlie! He needs a bit of reassurance and she makes him feel loved and safe when we're away!”
“Kari was an awesome sitter for Brew! She accepted our request at the very last minute (much appreciated) and her family showed him a ton of love while he was there. She’s a great communicator and very caring. Brew came home so tired from all of their adventures. Thank you!”
“Easy to coordinate with Nikkita & my toy poodle has a good time during the holiday week. Received pictures & updates, thanks for opening your services during the holiday period & having Killian as a guest.”
“Sadie had such a great time staying with Laura. She is very skeptical about new environments; however, she was very comfortable and showed no signs of stress. I will be asking Laura to watch Sadie again in the future.”
About: We are a family with a 13 year old girl, 9 year old girl, 2 sweet cats, 2 hamsters and a yorkie! All our animals are vaccinated and not aggressive. Our girls are animal lovers and have been caring for pets since they could walk! We are used to prioritizing pet needs and are home throughout most days and could likely accommodate the most unique needs - without judgment! We have 3 adults in the home and there is rarely no one home at all. One adult works part time and one works from home. Kids have school and sports but as a family, we are used to prioritizing pets’ needs regardless of the daily schedule. We live in a beautiful neighborhood with nearby parks for walks and have a small back yard that is not fenced in. We have space for a crate indoors if needed, but also can provide lots of snuggles.
“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!”
“Edgar was awesome!! Day was right at home as soon as he got there. He loved having a friend to play with during his stay. We received great updates with pics. Perk for me is he’s right around the corner. I’ll absolutely be using him again.”
“Theo came home happy and healthy! Megan and Jacob sent daily updates with pics. Theo was happy, relaxed, and clearly well cared for the entire stay. I really appreciated the updates and the peace of mind knowing my pup was in such good hands. It truly felt like a home away from home. I will absolutely be bringing my dog back and highly recommend them to anyone looking for a safe, loving place for their pet!””
“Pamela was wonderful with our boy Vito, she took care of him like he was her own. We got tons of pictures, she took him for walks, Also he got to run around in her fenced yard, and she followed his schedule for foods and medicines. I would use pam again for sure when we need a sitter for him. Thanks Pam!”
“Ollie felt right at home. I loved the large fenced yard for off-leash exercise and that I got lots of picture updates. He enjoyed the extra company from other pups and children too. Thank you!!”
“Donna was wonderful! She accepted my dog on short notice, gave him wonderful care, and allowed me to extend his stay by a day. Bandit was a part of the family, and didn’t want to leave :) Definitely recommended!”
About: Hello furry parents! My name is Lily and I’m excited to support you and your family. I have worked with all dog breeds and all ages through fostering. I am currently in my training certification program to provide proper education to you and your puppers. I am an online student looking to spend my free time with amazing pets. My top priority is to give all animals time and love. Whether it’s giving a long walk, using my dog park at my complex or administering medication, I’m your girl! When I would care for your pets, it’s all about the greeting. I would love to make sure your pets are as comfortable with you as for me! If you’d love me to help them learn tricks, feel free to request!
“Pearl provided outstanding care for our dog once again. Based on how excited is he to be with her, it's obvious that she spoils him with attention. We are incredibly thankful for her dependability and trustworthiness. We know that he gets treated as well as one of Pearl's own and we will count it a blessing to have her care for him again.”
“Enrica took wonderful care of Luna! She provided frequent updates throughout the day and sent photos of their walks and cozy moments together on the sofa. It was clear that Luna was happy and well cared for. I would love to book her services again!”
The median cost per night for dog boarding in Chesapeake City 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.
How to book dog boarding
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 - Chesapeake City
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chesapeake City average 11 repeat dog boarding clients
FAQs for Dog Boarding - Chesapeake City
Frequently asked questions about Rover
The average cost of Dog Boarding in Chesapeake City is $61 per night as of October 2026. Most bookings cost between $32 and $71 per night. On Rover, 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 629 sitters on Rover offering Dog Boarding across Chesapeake City. 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.
96% of sitters in Chesapeake City 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 Chesapeake City home-away-from-home, 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 Chesapeake City.
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 Chesapeake City 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 , 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 .
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
