Dog Boarding Chesapeake City
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 131 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 the only sitter I trust to look after my senior dog when I go away. She sends amazing pictures and is great at keeping communication open. 10/10 everytime!”
“I would highly recommend Jen! I have basically never left my dog at home alone. I chose to have Jen watch him since I didn’t want to leave my dog for the first time at home for 8 hours or more. I had a good feeling about her. She was on time, ready, and happy to take my dog. In talking to Jen I could tell that she has experience with dogs and that she loves them! She reassured me when I left him with her and let me know what she had planned. Jen took pictures during their walk and at the park. She sent me pictures throughout the afternoon and evening. My dog was happy and not anxious at all. When I came to pick him up she was already downstairs with my dog and his things in hand. He was very happy. I will definitely book Jen again next time I’m in the D.C. area!”
“Andres was super easy to work with and provided me with great updates/pics. My dog was in really bad shape the last time I left him at a kennel but he was happy and healthy when I picked him up after a weekend with Andres. I will definitely use again.”
“Justin & Stephanie were amazing. I left dropping my dogs feeling at ease and came back to happy dogs. They also send a ton of pictures which I loved. So accommodating with my two dogs. Gentle & helpful with my senior dog with arthritis. Their home is set up perfectly to have multiple dogs and no issues. Definitely book your stay with them. They are a very genuine family and you can tell they love doing this.”
“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! :)”
“Pamela was very responsive and kept me updated throughout JuJu’s stay. She has a large, fenced in yard that provided plenty of space for play and exercise. It was clear that JuJu was well cared for, and I appreciated the regular communication and peace of mind. I would definitely recommend Pamela and wouldn’t hesitate to book with her again.”
“You just can’t get someone more kind, caring and perfect for your dog. Cindy was so good with our dogs Apollo and Jupiter. So many years of rescuing and working with dogs. Her knowledge about their needs and behaviors is priceless. She made them and us feel so comfortable. Thank you Cindy.”
“5 stars! Rita went above and beyond for our 14 year old Louis. She is very reliable, responsive, gives good updates and is very caring with her animal guests. We will definititely ask for Rita 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!”
“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!”
“Karen kept my 2 English Bulldogs and a 10 y/o Boston Terrier for a long weekend and they came home healthy and happy. Her attention to detail (food, wrinkle cream and brachycephalic considerations for heat exposure) along with the ease of drop off and pickup will make her a top choice for future boarding.”
“Fantastic sitter! Loving family! My lil dog is always in good hands. Very responsive and flexible sitter. GUARANTEED to care for your pet as much as you do. Thank you”
“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.”
“Elizabeth was great! She sent plenty of updates during our dog’s stay, which was greatly appreciated and followed all instructions when it came to him. She was also super sweet and her family was just as sweet, we felt very comfortable leaving Meechie with her.”
“Our dog seemed well taken care of and very happy when she was returned to us. Jenn has a beautiful piece of property for dogs to walk around. Both her and her husband were easy to deal with and provided daily updates”
“Sharon was wonderful with our dogs! She watched my two dogs and my sisters' two dogs for a weeklong vacation. Our pups are older and take oral medications as well as needing to go out frequently. Sharon handled their issues in stride, and even got my sister's timid anxious dog to warm up. They loved running around in the fenced back yard and snuggling up in the dog room with lots of spaces to take a break. Sharon sent pictures and updates throughout the trip. Would definitely work with Sharon again!”
“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! 💛🐾”
“Toby recognized yovonne and Joseph immediately and was relaxed from the get go. I got constant updates which I really appreciate, shows the effort they put into taking care of him. Definitely my go-to people for toby when ever I am going out of town.”
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
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 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 July 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 July 2026, there are 646 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.
Connect anywhere with the Rover app
