Dog Boarding Chesapeake
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 4,225 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.
“Wonderful care of our loved one Jodi. They provided excellent updates, photos and pictures. Responses were quick and accommodating to our nedd”
“Amber and Dave are awesome! I had a last minute work trip and needed help watching Winnie and they responded instantly and were able to help. They are super communicative, send great pictures and we’re very great about checking in on pick up/drop off times. We will definitely be using them again.”
“This was my first time using Rover, and it was a wonderful experience! My dog is 12 years old and blind, so at first I was anxious about leaving her under someone else’s care. Jiyali made me feel very comfortable with her listed experience and asking the right questions before dropping her off to make sure she would be comfortable and happy during her stay. She sent frequent updates, and in every photo and video my dog looked so happy to be there! The process was very convenient, and both me and my dog were comfortable with the care she provided and will definitely request her again. I’m grateful to have found someone that could ease my anxiety and make the experience wonderful. Thank you so much for everything!”
“I recently adopted a blind, deaf senior dog. I was very anxious about leaving him, since he was just starting to learn his way around, but I had a pre-planned trip out of town. Michelle had boarded my previous blind dog and I knew she provided outstanding care, so I asked her if she would be willing to board this one. She said yes, which helped relieve me a little, and reassured me that she would keep him safe. Little did I expect the level of service she provided! She sent me pictures of him daily, introduced him to other senior pets, and carried him around in a special harness while she did chores. I was able to relax and enjoy my trip without worrying! She is the only one I trust with my pets! You won't be sorry...she's fabulous!”
“Cassandra and Tradd were great hosts for Hazel. I could easily tell that she had a great time during the stay. We got regular updates and Christmas ornament with her paw print is something we are going to cherish! So fortunate to have such a caring family to look after our loved one!”
“She is wonderful! I was going out of state so I was a little nervous- but she is amazing at what she does. She suggested a meet and greet with dogs beforehand which was an excellent idea. Martina- thank you again!”
“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.”
“Marie was everything we could ask for! She communicated with us daily. She sent photos of our puppy playing and that made all the difference. Her back yard was big enough for our GSP to run around and enjoy herself all day. Thank you so much Marie!”
“Julianne is great with arwyn our 5 lb chihuahua. She takes care of her daily walks and specialized meals and treats her as one of her own pups. Arwyn is always happy when I come to get her, looking forward to booking with her in the future!!!”
“Hannah took great care of our dog while we were away. She sent us so many pictures and updates, took him on long “sniffaris,” and even took care of a little wound near his ear. Hannah is an experienced, caring, and dedicated sitter who clearly puts a lot of time and attention into the dogs she looks after. We felt very comfortable knowing he was in such good hands!”
“I contacted Daisy LATE for the possible care of my Dog as a previous Sitter was not a good fit...we had a Meet/Greet on same day I contacted her which went well!! and she agreed to watch him for the weekend! She sent pictures plus she has an older dog who is chill like mine and they got along fine!! Her and her husband, Walter really cool people who care about and for your pet. very clean house, plenty of fenced in yard for my dog to 'explore'. I highly recommend Daisy, husband Walter and their 'boy' Teddy!!!!”
“Kobie was super professional and nice through out this entire experience. I have a 3 year old GSD and he’s typically very active so I had some reserves about his first overnight boarding experience. Kobie reassured me and made me feel comfortable with his excellent communication and experience. Gambit had a great time and was on his best behavior. We will definitely be booking with Kobie again.”
“My kitties were so loved and cared for! This was the first time they went to a cat sitter and I can't believe how lucky we were to find such an amazing pet sitter! Thank you so so much🤩😍”
“Leah was very friendly and took good care of my Daisy girl. She also took my booking request really last minute, lifesaver! My pooch came back relaxed and happy, and apparently didnt have any problems with the super friendly resident lab.”
“Amanda was great! I couldn’t have asked for a better experience. She kept me updated to include pics of the dogs did so well with her. It set my mind at ease and was able to enjoy my short time away from home.”
“We cannot say enough wonderful things about wonderful Michele! Our anxious Shih Tzu can be very nervous around new people and changes in routine, but from the very beginning, she showed incredible patience, kindness, and understanding. She took the time to make Charlie feel safe, comfortable, and loved, and it truly made all the difference. We received updates, photos, and reassurance while we were away, which gave us complete peace of mind. It is clear she genuinely cares about animals and treats them like family. We are so grateful to have found someone we trust completely and would highly recommend her to anyone, especially those with anxious pets!”
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.
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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
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 is $38 per night as of October 2026. Most bookings cost between $27 and $53 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 1,010 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.
95% 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, 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 , 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 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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