Dog Boarding Chesapeake City
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 134 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 took amazing care of my little senior yorkie and he had a blast staying with her. She kept me updated while I was away and sent the cutest pictures. You can tell Barbra cares about animals and wants to make sure they are comfortable during their stay. I 100% recommend her services to anyone who reads this!!”
“They are amazing. Camilla had the best doggy vacation while I was on vacation. She had a ball.. I really appreciated the constant photo-op they gave Camilla. I found my new home away from home for my baby.. Thank you. Thank you. Thank you...”
“Zuri I know had a relaxing stay with Candice I got pictures everyday she was very welcoming I felt at ease leaving Zuri with her I would definitely recommend her !!!”
“Olive recently spent 8 nights with Jen. Jen was wonderful. I received 3-4 texts a day with lots of photos. Olive went on 2 or more long walk each day, got lots of love and plenty of belly rubs. Jen and her husband treated her as their own and she fit right in!”
“Sandra is an excellent sitter! Our dog Chico was very happy to be with her! Definitely we will go back to her as needed and certainly highly recommend Sandra as a pet sitter!”
“Karen kept McDuff overnight. He had so much fun with Karen that when it was time to leave he was not sure he wanted to leave and he was sacked out on the couch for hours. Thank you Karen for taking good care of McDuff!”
“Lindsey is an amazing sitter!! She shows a lot of love to Chico and he loves her back. Chico came back to us clean, well fed and with no issues. Lindsey's children are very fond of him too. And I appreciate the fact that she sends me pictures of him at play with his furry friends every day. That keeps me at peace to know he's having an enjoyable stay.”
“Jill & Tommy were great! Milly had a great time playing with 5 new friends and we were kept updated with texts & pictures daily. Today she seems lonely with just me on a rainy Monday. Paul & Marybeth”
“Sharon was a very helpful and courteous sitter! Mazzi had a blast staying with her. Highly recommended her as a sitter her property and home is absolutely gorgeous and perfect for long stays! Thank you so much for taking such great care of our girl!!!!”
“My Maltipoo stayed with Yvonne for 2 nights and was very well cared for. I'm sure she enjoyed the nice yard. Yvonne was very easy to coordinate with and sent lots of pictures and updates. Her dog was well mannered, and her house was well kept. We will definitely want to use her again.”
“Laura was a fantastic dog sitter! She was flexible with scheduling pick up/drop off, sent an update with a photo, and our pup seemed to have a great time with her. We will definitely use her services again!”
“We are new to the area and we’ve always had friends or family watch our pups. This was the first time we needed to use Rover. Nancy gave us a great first experience and I’m so glad we have someone we can trust to leave our pups with if we ever need to board again! She asked great questions to get to know our pups before us dropping them off and she kept us up to date everyday with plenty of pics and videos. Nancy was very responsive as well. We will certainly be reaching out to her for future needs. Thanks again Nancy!”
“Claudia took such amazing care of my dog! She shared lots of photos and detailed updates every day, so I always knew how he was doing. She not only took him out for walks but also played with him at home and even let him snuggle with her at night. My pup absolutely adored her — when it was time to leave, he even sat on the lawn refusing to go, with watery eyes. It’s clear he felt very loved and happy with Claudia. Highly recommend her to anyone looking for a caring and trustworthy sitter! 💛🐾”
“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!”
“Rackeem was the best! From his knowledge and expertise in handling dogs to his professionalism and consistent photos/updates. Thank you so much for watching my baby for the weekend. I will definitely be booking with you again. Marley seemed to really love his stay and made a new friend!”
“Latoyia was great my dog got the attention she needed and was well taken care of i will definitely be booking her again she was. amazing and responds very quickly along with making sure i had updates”
About: I have taken care of dogs, my whole life whether they were my own or somebody else’s I absolutely love animals your animal will always be safe in my care and have the best time. I’m currently a stay at home mom so if I leave the house, I only leave to go to the grocery store or to grab the little one something to eat if they want it I have a huge backyard my house backs up against the woods. We are not close to the road at all. You’re dog would never be let outside alone my kids would run around in the backyard with them 💕
“Kari, Joseph, and their kids were phenomenal with our last-minute booking of our boxer, Peanut! Their home is beautiful and spacious in a lovely neighborhood. They’re communicative, provided a crate (which made our lives so much easier). They were flexible when we were a few minutes late to pickup and were totally understanding. We’ll absolutely book with them 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.
Meet local sitters who will treat your dogs like family
1. Search
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3. Book & Pay
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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 Boarding - Chesapeake City
Frequently asked questions about Rover
The average cost for Dog Boarding in Chesapeake City on Rover is $61.05 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 643 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 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.
91% of Chesapeake City 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 Chesapeake City 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 Chesapeake City 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 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 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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