Dog Boarding Chesapeake
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 4,233 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.
“María and Mathew were great with taking care of ares, i constantly got updates and pictures while they took care of him and he looked happy the whole time, i would recommend them as dog sitters 😁”
“Julie and Kenny were awesome! They took the best care of my dog and she loved it there! They sent messages and pictures of her. My dog felt right at home in their place and they treated her like one of the family. She even slept with them at night in their bed! I will definitely have them watch Daisy again! :)”
“Penny was so comfy here! She always takes a second to warm up but I can tell she had a great time. They sent me pics through out my trip and I didn’t worry a bit about her. It was so nice knowing she was taken care of and they’re close to the airport which is a huge plus. Definitely will be rebooking!”
“Michelle did a great job of looking after Truffles for a couple of weeks while we were overseas. She was really friendly when we met her and kept us updated each day with how Truffles was getting on and also texted us a picture every day. We'll definitely be using Michelle again when we go on vacation.”
“Melanie was amazing! She sent pictures throughout the day to reassure me that my baby was okay while I was in vacation. I will definitely book with Melanie again.”
“Our dog had a great first stay with Gail and her daughter. We received pictures showing how our dog felt comfortable and relaxed :-). Thank you both for a great experience!”
“Kathleen was so nice! Her and her husband kept in constant communication while I was gone to give me updates on my doggy and send me pictures. She even bought my dog a new toy! Kathleen went above and beyond watching my dog for 2 weeks during the holidays. She was amazing!”
“Mark really looked to enjoy his stay and I was provided photos and videos throughout the stay. It was nice to have a yard for him to run and a family who you can tell loves all those they care for.”
“Lisa and her family took wonderful care of our little dog while we were away. They treated him like part of their family—lots of attention, playtime, and updates that gave us peace of mind. We came home to a happy, relaxed pup, and it was clear he’d been loved and well cared for. We’re so grateful for their kindness and would absolutely trust them again in the future.”
“Our dog Lilly loves being with Tina and family! She is super happy to be at Tina’s! Tina sends us pics and provides us updates regularly…. We love ❤️ Tina!”
“Martina was great with our pets. She sent pics and daily messages while we were away. She was very patient with them and cared for them as if they belonged to her. Would use her again if we needed to.”
“Rebecca was Amazing! She worked with Peanut, maintained the limitations that we established at home and communicated frequently via text message and videos! It takes me 30 mins to get to her, but it is 1,000% worth it!”
“David was amazing and truly understanding. Our children had a track meet 4hrs away that went over in time by 3-4hrs. David’s flexibility to still provide loving care for our furbaby meant a lot to us.”
“I had an amazing experience with Beverly ! She took care of my dog for a full week and went above and beyond in every way. Not only did she keep me updated regularly with pictures , but my dog was clearly happy and well-cared for the entire time. On the 6th day, she even gave him a bath. It’s such a relief to know your pet is in good hands, and I wouldn’t hesitate to book her again. Highly recommend!”
“10/10! Cassandra and Tradd were amazing!!! Cassandra sent me photos throughout my pup’s stay, and gave frequent updates. She was very responsive and super friendly! Great home, great people. Will be using again!”
“Wendy was so great!!! I felt 100% comfy leaving my Ellie boo with her. She sent me sweet cuddling pictures while we were away and took the best care of our girl. She was loved on like family, no doubt about that. EXTRA thankful for her help getting in/out at pickup while I was SOLO in the weather🤣 the sweetest human. We will def be using Wendy in the future. 10/10 recommend!!”
“Our pup Keena had such a blast there! Kobie sends tons of video updates which were the highlight of our trip getting to see her having so much fun with the other dogs under his care. Definitely recommend and will be using him again!”
“Gail was AWESOME! Our Kobe is always skittish when meeting new people but she got him to calm down right away. She is a STAR SITTER for a reason! Highly recommended and we will rebook for sure! Thank you Gail!”
The median cost per night for dog boarding in Chesapeake is $40
Dog parents share their Rover experiences - Chesapeake
We truly appreciated Michelle taking very good care of our Indie girl. Michelle knew we were anxious leaving our pup for overnight stays, but she did a great job keeping us posted with pictures and activity updates. We will reach out again to book Camp Chelley in the future! Thanks again, Michelle!
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!
This was our dog’s first time staying with a sitter, and unfortunately the experience did not meet our expectations. Prior to booking, we were very transparent about our dog’s needs, including her separation anxiety, walking and feeding routine, and tendency to bark, so the sitter could determine if this was a good fit. The sitter assured us this would not be an issue, noting that our dog would be the only dog in her care, would receive undivided attention, and that she has years of experience caring for dogs. Prior to drop-off, we were informed that she had recently gotten a puppy but were told this would not interfere with our dog’s care, which I strongly believe that it did and overwhelmed her. We also provided two days’ worth of anxiety medication and had explained that this was the first time our dog had ever taken medication. Despite this, we were asked if someone could bring additional medication, which felt uncomfortable and unexpected given our prior conversations. Overall, we wish there had been better alignment between what was discussed before the stay and what the sitter was prepared to handle. Instead of peace of mind, this experience caused additional stress, and our dog returned home noticeably more stressed and slept for several days, which is very unusual for her. Overall she is a very nice person with best intentions but I guess our dog just required more one on one attention since this was her first in 9 years being with a stranger.
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?
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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
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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 Dog Boarding - Chesapeake
Frequently asked questions about Rover
The average cost of Dog Boarding in Chesapeake on Rover is $38 per night as of October 2026. Most bookings cost between $27 and $53 per night. 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 1,021 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 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.
97% of sitters in Chesapeake 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 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.
<b>Tip:</b> 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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