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.
“Barb was fantastic! We chose her because of her experience with dogs of all ages, especially older pups. Although our pup was a bit nervous, she seemed to settle in well and made herself at home. Really appreciated the updates and pics to let us know all was good.”
“Laura was great. She took wonderful care of our sometimes difficult pup and he loved being there with her and her pup Eugene. We’re going away for 10 nights soon and Laura is our first choice of sitters. We definitely recommend her to anyone needing a caring, supportive sitter in their home!”
“This was my first time boarding my 6-month puppy, but Claudia eased all my worries. I got tons of pictures and updates that gave me peace of mind. I could tell Stella had a great time. If you’re unsure about boarding your pet for the first time, you can trust Claudia!”
“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!”
“Karen and her husband were very nice. Never hesitated to answer my text when checking on Charlie and even sent pictures. I would highly recommend Karen to others and will use her services again.”
“Stevie absolutely LOVES staying with Robyn. We also greatly appreciate her communication while Stevie is with her. It is evident Stevie is treated like family when she stays! Thank you Robyn!!!”
“Rita did such an amazing job with Rocco. She kept me updated the whole time I was away and made me feel extremely comfortable. Your dog will be in good hands with Rita!”
“Amy and Thomas did an amazing job caring for Peter. He came home happy, healthy, and calm. I'm glad he had the opportunity to interact with their dog Phoebe. Phoebe is delightful and friendly. They communicated with messages and pictures throughout Peter's stay. We would definitely book with them again!”
“Thomas was fantastic. We got updates and photos of our babies everyday. He was super responsive. Our babies played, had fun, and were happy. We definitely will be booking again.”
“This was our first time boarding our dog, and we couldn't have asked for a better experience. Chyann was incredibly sweet, attentive, and caring, and it was clear from the start that she genuinely loves animals. She provided regular updates, photos, and messages, which gave us so much peace of mind while we were away. Our dog was well cared for, comfortable, and happy throughout the stay. She has a natural way with animals and made the entire experience stress-free for both us and our pup. We would absolutely book with her again and highly recommend her to anyone looking for a safe, trustworthy, and loving environment for their dog.”
“We find Mike to be easy going and attentive. We appreciated the updates and pictures that he sent us throughout the weekend. Ruby came home very tired from a fun weekend playing with Mike's puppy. He even texted us the following day to ask how Ruby was doing. That was so thoughtful. Would definitely use his services again.”
“Elizabeth was a wonderful sitter for Odie. She was very attentive to his specific needs and was more than capable of handling my 85lb Shepard mix. Odie was relaxed and happy while I was away even with his severe separation anxiety. 100% would recommend her as your next sitter!”
“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.”
“Jenny took exceptional care of our two pups while we were away on vacation. She provided daily updates along with photos, which gave us great peace of mind knowing they were happy and well cared for. Both of our dogs are rescues, and one of them is especially shy and requires a little extra patience and TLC. Jenny went above and beyond to make sure he felt safe, comfortable, and loved during his stay. It was clear she truly cared about their well-being and treated them like her own. We couldn't be happier with the care she provided and will absolutely be using her again for our next vacation. Highly recommend!”
“We were so satisfied with the care and service we received from Bethany. Our puppy Nala and her dog Star got along phenomenally. We received updates and photos daily via Rover as well as text messages from Bethany letting us know how Nala was doing. We will definitely be using her again whenever we travel. Thanks Bethany! ”
“The fact that Courtney is a vet was one of the reasons I reached out to see if she was able to watch Sunny for a weekend while I was out of town due to how anxious she can get. Let me tell you, she did not disappoint. During the meet and greet, she asked about emergency vet info and offered her office as an option for urgent but non-emergency situations since I don’t have a primary emergency vet. She was aware of Sunny’s needs while she was there. Courtney also kept great communication and sent lots of videos and pics during her stay. I would 10/10 recommend her and will definitely be booking services with her again when the time comes!”
“Jen immediately put us at ease. Her positive energy and love of dogs came through at our very first meeting. She regularly sent us notes and pics of our dogs, which we really appreciated. Thank you Jen! We will definitely call again if we need a sitter!!”
“My two dogs were well taken care of and also Amber was very informative and also sent me pictures of my pets while I was away. I would definitely recommend her and also I would definitely hire her again. Thank you”
“I was so relaxed with leaving Rex with Elise. Rex loved Elise with in few seconds and felt comfortable at her home. Elise was very flexible and accommodating with drop in and pick up times. Will definitely use 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.
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.
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