Dog Boarding Chesapeake
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 4,116 pet parents in Chesapeake have booked dog boarding
Chesapeake, 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.
“Coop loved his time with Maria and Matt! They made Cooper a part of their family and he had a great time ☺️ coop is already looking forward to his next visit!”
“Caring sitters. Julie provided me with daily updates and pictures of my babies. This is the longest stretch that I had left them and the daily updates made me feel better. I will definitely use their services again! Thank you, Julie and Kenneth, Ethan and of course Louis, their fur baby.”
“I highly recommend Maryann! From her initial response to my request for pet sitting, to her multiple updates every day (with pictures), MaryAnn conveyed a professional and loving option for our little Puggle. We will definitely use her sitting services again!”
“Melanie is amazing! We had an impromptu trip to the beach and it was too hot for the doggo. She was super responsive and has the perfect place for dogs to go! Will use her again if I’m heading to the beach!”
“Exceptional! Super communicative and clearly took care of Hanzo like he was their own. Incredibly happy with how well they took care of him! Will absolutely book again!”
“Sherry and Brad took great care of Roxy! The family atmosphere was so great for her. I received pictures during her time there which helped me feel secure that she was doing well while I was away. I would definitely book again in the future!”
“We had a great experience with Kathleen, great communication. Even before we dropped off our dog she was communicating with us and answered any concerns I had. Stays in contact and is great with keeping you updated with what the dog is doing through great videos and a lot good pictures. If you’re looking for a great person to take of your dog you found the right person. Thank you for everything Kathleen.”
“I would definitely recommend Stacy. Bentley enjoyed his time with her. She sent pictures and gave updates so I knew he was in good hands. She super responsive , definitely rebooking 😊!”
“Beverly is such a sweet and gentle dog sitter! She sends updates and is always out and about walking the dog, taking him on errands, and giving snuggles. He always smells better than when I dropped him off haha; that’s a plus! It’s definitely a vacation of love and fun for my fifteen year old chorkie! Will continue to resource her for care.”
“I would definitely recommend Megaan for anyone and their fur babies. Meagan‘s communication was top-tier and she provided us with a picture of our boy every day. We felt extremely safe leaving him with her. Meagan was very attentive to any instructions that we left. We definitely plan to rebook with her in the future.”
“Wendy was awesome taking care of our pup on short notice! She was very accommodating to our schedule and made logistics easy. It was clear Ollie felt right at home. Highly recommend!”
“Lauren and her wonderful family are the very best sitters and genuinely love dogs. This is Ollie's second time visiting, and I know he's happy and loved; he always has a blast playing with Lauren's dog, Milo. Thank you!”
“Michelle did an amazing job taking care of our 10 week old puppy. We received a ton of photos of pup. Also, our dog had a chance to interact and play with other dogs, which is important for us. Our pup had an amazing time that she did not want to leave. ”
“Cassandra and Tradd we're just Amazing with my Mac! I was so nervous leaving him for the first time with someone I didn't know, but that quickly changed after I met them and their little pack of cuties! Mac had the best time being spoiled, cuddled, and loved by their family! I will definitely be calling on them again and again! ❤️”
“Tina did an excellent job caring for my two year old Bichon Frise. It was her first time staying the night at Tina’s house and she did a great job making her feel comfortable. Tina has excellent communication skills and her calm demeanor helped my pup get acclimated to her house during her stay.”
The median cost per night for dog boarding in Chesapeake is $40
Dog parents share their Rover experiences - Chesapeake
I’m so grateful that he was able to watch my dog on short notice! He was incredibly accommodating and made the whole process so easy. He is also a great communicator and kept me updated, which gave me peace of mind while I was away. I truly appreciate his flexibility, reliability, and care. I would definitely recommend him to anyone looking for a trustworthy and dependable dog sitter!
Blaine was very responsive when I scheduled. We met and he was very personable and easy with the dog. we took him to his home as we felt comfortable with him. His house is quiet and calm which we really appreciated. Blaine was very loving with our dog He sent us one picture when he calmed down. we were not interrupted on vacation, but he did response promptly to my text. I will absolutely allow him to sit for us again. Our dog has definitely decided he likes Blaine and bonded.
Once again I had Madison watch my dog Cooper. She is absolutely fantastic with him and takes great care of him. Not even joking when I went to drop them off he took off down the street and ran right to her door. He was so excited. I know it's hard to find a good dog sitter but Madison is one of the best I have ever had.
Isaac took excellent care of our dogs, Duchess and Jojo, while we were away on a week-long cruise. His communication was great throughout our trip, and we really appreciated the frequent photo updates. We picked up our pups happy, healthy, and clearly well cared for. We would absolutely recommend Isaac to anyone looking for a reliable and caring pet sitter.
Very easy to drop them off and pick up, Brandon came to help and was super friendly and very welcoming for my chaotic kiddos. He did a phenomenal job taking good care of them while I was away. I got lots of pictures of their walks and the fun things they did this amend. I was worried because one of my boys has an anxious attachment personality due to his upbringing before I adopted him, but that wasn’t much of an issue with him due to the comfort and care that was provided. Extremely happy with the service (:
Thankful to Paul and his family for accommodating Bo and Jackson during a challenging sitter scheduling. He picked up my dogs from another sitter, identified some pet injuries, and reported them back to let me know my pets were safe and secure. Thanks to him and his family for providing me peace of mind.
Zimir was absolutely great. We had some last minute changes to our plans and he was able to watch our dogs on short notice. He provided lots of updates, as well as pictures. I definitely recommend Zimir. He was great at communicating as well. Thank you very much Zimir!
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
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3. Book & Pay
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Popular requests for dog boarding - Chesapeake
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chesapeake average 12 repeat dog boarding clients
FAQs for Boarding - Chesapeake
Frequently asked questions about Rover
The average cost for Dog Boarding in Chesapeake on Rover is $37.45 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 1,025 sitters on Rover offering Dog Boarding across Chesapeake. 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.
97% of Chesapeake 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 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 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.
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 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 VA 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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