Dog Boarding Chesapeake
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 3,915 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.
“As usual, everything went perfectly good for Hector, with Amber and Dane. And we see Hector truly loves them and is totally exciting when we are driving him to them. Amber and Dane genuinely love dogs, considering the ones they are sitting as theirs and this makes us fully confident when we have no other choice than leaving Hector while we have to travel.”
“I have boarded Cookies more than a dozen times over the past 12 years and Julie will be my go to dog boarder! She asked great questions before drop off and communicated the schedule at pick up so we could stay on schedule at home. She sent me several pictures while I was away so that I could see my fur baby. She let me know how she was adjusting to her environment from the moment she arrived. She shared that my senior dog wasn’t ready to get up when the rest of the family was ready, so they let her sleep in❤️. When my fur baby was leaving, she looked back at the door to see if Julie was coming with us. I look forward to my next trip because I know I can relax and not worry about my dogs’ care.”
“Megan is absolutely amazing. She will send pictures and videos of your pup to keep your mind at ease along with text updates through out the day. It is so appreciated and can't recommend Megan enough!”
“She took care of my dog like her own. I highly recommend her. She kept me in the loop by sending pictures all the time. My dog had a great vacation and was very happy in her care!!”
“Cassie had a great time during this stay! Lots of walks, play time, and snuggles. She was very well taken care of and we received many pictures/videos over the two weeks. We would highly recommend and will plan to book with Maria and Matthew again in the future!”
“Charlie had an amazing stay with Stacy and fam! He got to play outside in a fun fenced-in yard with another fur friend and human friends. He also got to eat some natural dog treats. He will be back!”
“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!”
“Beth and family were great with Biscuit! She sent lots of pictures of Biscuit living his best life and playing with her dog. Communication was great, and drop off and pick up a breeze. We did a meet and greet as Biscuit can be afraid of other dogs, and it went well. Would book with Beth again!”
“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!”
“Meagan was awesome! Especially with a last minute booking, she was available for meet and greet prior and asked and answered any questions with ease. Throughout the stay her communications were excellent and she sent great pictures. We didn’t worry on our trip because we knew Lyra was in great hands! We knew Lyra was treated as family while in her stay! Would 100 percent book her 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!”
“Beverley is kind an has shown to be a second doggie mom to my Gio. He was happy and well taken care of in my absence. Will definitely use her services again.”
“Had the best experience! And the fact that she was able to accept a last minute booking was sooo wonderful! My fur baby was well taken care of ☺️ Would recommend! 10/10”
“Cherry was wonderful with our Roscoe! She was available last minute and spoiled us (and him!) with walks and snuggles and we got tons of photos during his stay! Will absolutely book again when the need arises!”
“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!”
“We've been using Jenn for over a year now, and every experience has been absolutely wonderful. She takes such great care of our dogs, they always come home happy, relaxed, and clearly well-loved. Jenn goes above and beyond with regular updates and tons of adorable photos, which gives us so much peace of mind while we're away. We feel incredibly lucky to have found someone so dependable, kind, and attentive. Jenn is truly an amazing sitter and we wouldn’t trust anyone else with our dogs!”
“Cassie and Tradd were the BEST home away from home for our dog! They sent us lots of updates and he was always smiling so wide, we knew he was well loved. We cannot recommend them enough - they have definitely become our go-to Rover family!”
The median cost per night for dog boarding in Chesapeake is $40
Dog parents share their Rover experiences - Chesapeake
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.
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!!!!
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
2. Meet In Person
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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 $36.63 per night (as of August 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 August 2026, there are 998 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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