Dog Boarding in Chesapeake
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Chesapeake dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Mckayla did such an amazing job watching my Willow over the holiday weekend. The updates were consistent and the photographs were adorable. You could see how happy and comfortable she was spending the night and playing with the other dogs. We will be boarding with Mckayla again!”
“Kathleen is truly a gem! I cannot recommend Kathleen enough as a dog-sitter. From the moment we met, I felt completely at ease leaving my fur baby in her care. She’s reliable, caring, and genuinely loves animals—which shows in every interaction. Kathleen took the time to get to know my dog’s personality, quirks, and routines, and kept me updated with adorable photos and messages while I was away.”
“Megan took care of my Wilson for two weeks and I’m so thankful I found her! Her and her family took such good care of my boy and I was so appreciative of her daily updates and photos. Thank you Megan and we will see you again!”
“Samson has stayed with Julie and Kenneth several times this year. Samson is an elderly dog set in his ways, and I can tell he is very comfortable with them. They keep me informed of any issues, and I am so happy to have found them!”
“Kaitlyn was a amazing. When I dropped my dog off, I was extremely nervous and so was my dog. Kaitlynn kept me updated to put my mind at ease. My dog was clearly comfortable. I would definitely use Kaitlynn's services again”
“10/10 best sitter in the area. Recieved updates about my pup throughout the day and the engagement he had at his stay was top tier. Definitely will be returning for all future needs!”
“Louis had a great time with Gail while we were in Norfolk for a conference. He enjoyed her large backyard, the company of her two chihuahuas, and even sleeping on the bed. She sent us lots of photos and updates during Louis’s stay. We would definitely recommend Gail for dog sitting.”
“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!”
“This was our second time with María and Matthew, and once again they were fantastic! I feel so at ease knowing my fur baby is in such loving and reliable hands. Highly recommend!”
“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!”
“Awesome sitter! Felt nervous trying Rover for the first time and he David 100% made me feel good about leaving my dog in his car. My dog felt so comfortable and happy at his house!!”
“Lauren was wonderful and Winston was in such great hands. We got pictures of him and we knew he had become a part of their family during our trip. Winston gives his stay 5 stars too! Thank you Lauren!”
“What a wonderful experience with Cassandra and Tradd! Excellent communication arranging appointment! My little guy loved being with them and Cassandra sent great pictures and videos of him immediately becoming one of their family. Will definitely be using their services again, next week in fact! Loved every bit of the experience. Highly recommended!”
“Shayla was fantastic! Daily updates to let me know how my pup was doing gave me peace of mind while away. She was also flexible with times and very responsive via text.”
“I cannot thank Rachel and Andrew enough for always taking care of my Bella. They’re the best and are so accommodating to make sure she always have the best time. As long as we’re living in Hampton roads, they’ll always be our first choice. Thank you both so much.”
“Simply put, if you're anywhere within driving distance of Michelle this is where you want your pet to stay. She does this for a living, not as a side job, and you can clearly see the experience and quality of care she's going to give when you meet her. Don't waste your money and have to worry about whether your animals will be taken care of properly by going to another sitter. It's not worth the stress when you can leave them with Michelle and have peace of mind knowing they will be cared for. She will have our business as long as we are in the area!”
“Absolutely wonderful! My spoiled and picky old man stayed with Lillian and Timothy for the first time, and I could not have asked for better and more considerate care. They cleverly found ways to get him to take his medication when he was being fussy with his usual turkey wraps. And they sent lots of pictures of him enjoying walks, having cozy naps, and getting plenty of attention and love. 10/10 recommend!”
“This was our first time leaving Brody overnight in a new place since we got him as a puppy. Beth and her family took great care of him! Her dog Khloe is very sweet and playful and they got along great despite the size difference. Beth is very nice, personable and communicated with us often and put us at ease with leaving Brody in her care. I would use Beth again in the future!”
“Kobie was great to work with! He is very quick with responses and accommodating. We got daily videos of our pup’s visit and he came home happy. Definitely recommend him and will use his services again.”
“Wonderful! Mango was very well taken care of, I felt very comfortable having her stay with Shannon. As happy as mango was to see me when I picked her up she was so sad to leave all her new friends ! Will absolutely rebook and do recommend her as a sitter.”
Over 4,501 pet parents in Chesapeake have booked dog boarding
Chesapeake dog parents share their Rover experiences
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 (:
⭐⭐⭐⭐⭐ We absolutely LOVED Michelle! You truly won’t find anyone better to care for your fur baby. Michelle treats every dog like her own, and the daily updates and photos gave us complete peace of mind. It was obvious our pup was having the BEST time playing with Michelle and the other dogs. When she got muddy, Michelle even gave her a bath immediately and she even sent her home spoiled with treats and a brand-new harness! We are beyond grateful and cannot recommend Michelle highly enough!
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!
We’re so grateful for Mia!!! It was a last minute decision to go out of town for the holiday weekend and Mia was available to watch our pups!! She was good with keeping in touch with us through texts and pictures! We were really comfortable leaving our pups with her! She did an AMAZING job with them and we will definitely use her in the future!! I would give 10 stars if that was available!! THANK YOU MIA!!! ❤️
Popular requests near you
Select a filter and find qualifying Chesapeake sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Chesapeake is $40
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Chesapeake average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Apr 2026, the median cost of dog boarding in Chesapeake is $40 per night, including service fees. Boarding your dog for one week typically costs $280. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chesapeake dog boarding rates can be found as low as $25 to as high as $49 per night.
As of Apr 2026, 1,050 sitters provided dog boarding in Chesapeake. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 95% of Chesapeake dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chesapeake have an average of 17 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Chesapeake.
Rover makes it easy to find Chesapeake dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 1,050 dog boarding sitters in Chesapeake on Rover, so you’re sure to find the perfect match for your dog! In Chesapeake, 97% of sitters offer daily exercise, 98% offer medication administration, and 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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