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.
“Our other dog passed very recently and has been with Milo for life so leaving him was especially difficult. We typically board and this is our first time using rover. Barbara reassured us and sent photos/updates throughout our time traveling. Response time and communication was top tier. I could tell he felt comfortable and safe in her home and was happy as can be despite the circumstances. I am so happy we opted not to board. 10/10 recommend and would happily work with barb again.”
“I was really nervous about leaving my husky for a week. After meeting with Justin I was more at ease..till drop off day..then it all hit..Justin kept reassuring me that stratus would be fine and I felt better..but when I got the 1st update and I saw him playing with other pups and that goofy husky tongue hanging I knew he was ok. Justin and Stephanie were great with pupdates and communicated throughout the stay. If I messaged they were quick to respond. My boy came home happy healthy and I would recommend Justin to anyone. They provided pictures and messages. I was at ease knowing he was well taken care of. Will be using again as we do have a couple more trips planned”
“This was our second time booking with Jill and Thomas, and once again, we had a wonderful experience! They took care of cucu for an entire week. They were incredibly responsive, provided daily updates (which gave us so much peace of mind), and were always quick to answer any questions we had. It’s clear they truly care about the pets they watch. We are so grateful to have found someone we trust with our pup, and we’ll definitely be booking again! :)”
“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.”
“Kayla was great and was able to accommodate me and my dog on very short notice. She’s incredibly caring and was great with updating me during my boarding time. Will definitely use her services again.”
“Yvonne K was a pleasure to work with. She communicated quickly and clearly. Most importantly, our dog seemed very content in staying with her. I also liked the fact that she has a dog who kept my dog company.”
“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 is a true professional. He’s knowledgeable, compassionate, detail-oriented, responsive, and kind. We love being able to leave our dog with him, always knowing she’s getting the best care and attention when we’re away. He also always leaves us with great care tips and suggestions. Thank you, Rackeem!”
“Lindsey took care of Sydney for a night. When I was there to drop off, the kids and the family welcomed Sydney and made her comfortable. Lindsey provided frequent updates which I greatly appreciate. Sydney had a great stay at Lindsey's.”
“Peter loves going to Geosselyn's house! She sends the cutest pictures of him during his stay there. Peter loves exploring her large, fenced-in yard. Peter comes home well rested and calm. You can tell that Geosselyn loves caring for dogs. We will definitely book again with her!”
“Mark and Kayleigh were amazing, start to finish, while watching our sweet pup. They both clearly know and love dogs, their house and yard and wonderful and safe for pets. They were attentive to the dog, responsive to us while we were on our trip, and operate with respect and professionalism you’d hope for when letting someone watch over a part of your family. Can’t recommend them enough! Our Shiloh will absolutely be staying with them again on our next trip.”
“First time using Rover, Sharon was great with our Doxie gave decent communication and pictures during our puppies one week stay After the week puppy was happy and showed she had been cared for during her stay. Would use Sharon again for future sitting.”
“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!”
“Latoya took wonderful care of my Morkie, Cam, for two weeks while I was away. She sent photos and videos which gave me peace of mind. Cam looked happy, comfortable, and well cared for. Latoya patiently handled all of his little quirks. She made him feel at home. I wouldn’t hesitate to book Latoya again and highly recommend her to anyone looking for a caring and reliable pet sitter.”
“Rita was great! Our first time using Rover and we were nervous since our dog can be a bit needy. Rita would send pictures and updates which put us at ease. Otis looked to have a great time! We will definitely be using Rita again.”
“Superb experience in all aspects. Initial inquities, booking process and all communications were expedient and clear. This was the first time boarding for our 7 month old puppy (song with his 4 year old "sister". Alexandra having experience with Great Danes was so very helpful and made our fur babies feel welcomed and loved. They especially enjoyed time with the girls! Unfortunately (for the sitters) the weather was rainy throughout, but Alexandra and daily were up to the challenges of wet pups with muddy paws. In addition, the younger one's night separation anxiety required some medication and thoughtful handling, all of which was accommodated and communicated with ease. The dogs were extremely well cared for and loved, and we received regular updates. Simply put, we couldn't be happier and will definitely use their services again whether for short or week long needs in the future. We recommend them with absolute highest praise and confidence!”
“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.”
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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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 for Dog Boarding in Chesapeake City on Rover is $61.05 per night (as of September 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 September 2026, there are 640 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.
92% 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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