Dog Boarding in Chesapeake City
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Chesapeake City dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Barb was fantastic! We chose her because of her experience with dogs of all ages, especially older pups. Although our pup was a bit nervous, she seemed to settle in well and made herself at home. Really appreciated the updates and pics to let us know all was good.”
“Tabby came through for us when we were in a pinch with finding a place for our two boxers and we are forever thankful.. Our boxers certainly enjoyed their time in her big back yard.”
“Olive recently spent 8 nights with Jen. Jen was wonderful. I received 3-4 texts a day with lots of photos. Olive went on 2 or more long walk each day, got lots of love and plenty of belly rubs. Jen and her husband treated her as their own and she fit right in!”
“Justin & Stephanie were great. We asked for a last minute booking and they immediately said yes. Many pictures were sent and even a video. Our chocolate lab had a great time!”
“Rackeem was the best! From his knowledge and expertise in handling dogs to his professionalism and consistent photos/updates. Thank you so much for watching my baby for the weekend. I will definitely be booking with you again. Marley seemed to really love his stay and made a new friend!”
“Chance was comfortable and happy in her care. I love that she sends photos. He was in great spirits when I came to pick him up. Will use her services again in the future”
“This was our second time booking with Andrea and she continues to be amazing! She took great care of our golden retriever, Bumi, even after he ended up needing stitches the week before our trip and had to wear a cone during his stay. She was super accommodating and made sure he was comfortable the whole time. We got tons of updates and videos, and it was clear he was in great hands.”
“Lindsey did a fantastic job caring for our 6 month old pup. She communicated a minimum of 2x per day and always provided pictures with each communication. We will definitely be using Lindsey again in the future.”
“This was our first time staying with Yvonne, Joe and Quincy. They have a beautiful patio and a good size backyard for sunning and exploring. Our dog Lilly loves Quincy (and Yvonne and Joe) and made a few new friends during her staycation. We were sent numerous pictures several times every day which was AWESOME!! Really confirmed that we could enjoy our vacation knowing that Lilly was in a great environment. We highly recommend them and we definitely will use them again in the future.”
“We were extremely nervous with having our dog stay with strangers but meeting Jill and Thomas quickly changed our hesitation. As soon as you meet then you can tell they are dog lovers. We recieved photos all weekend and our dog was having a great time. We will definitely be returning as a client.”
“Claudia took such amazing care of my dog! She shared lots of photos and detailed updates every day, so I always knew how he was doing. She not only took him out for walks but also played with him at home and even let him snuggle with her at night. My pup absolutely adored her — when it was time to leave, he even sat on the lawn refusing to go, with watery eyes. It’s clear he felt very loved and happy with Claudia. Highly recommend her to anyone looking for a caring and trustworthy sitter! 💛🐾”
“Cynthia was great with my 1 1/2 year old Sheltie. She allowed us to meet her and her pup a couple of weeks before our vacation, to make sure we all were comfortable with each other. Drop off day was hard for us since our Sheltie is only 1.5 year’s old and a rescue, we didn’t want to stress her out too much. Cynthia has lots of experience with rescues and was quick to pick up on her needs. During the vacation she sent us many videos and pictures, which helped a great deal. On pick up day she sent us home with homemade treats, bully stick, and a freshly laundered dog bed. I will definitely use Rover and Cynthia again!!!!”
“My lab Ruby had a wonderful time with Jacob and Megan. She was super excited that she would be able to play with other dogs and lounge on their deck. She was exhausted when she came home. I definitely recommend Jacob and Megan as dog sitters and would take Ruby back again!”
“Chelsea is wonderful. She really took great care of my dog. From the video she sent me, I can see that my dog loves her. I will book her again next time. Happy New Year!”
Popular requests near you
Select a filter and find qualifying Chesapeake City 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 City is $50
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 City average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, 374 sitters provided dog boarding in Chesapeake City. 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, 91% of Chesapeake City dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chesapeake City have an average of 21 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 City.
Rover makes it easy to find Chesapeake City 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 374 dog boarding sitters in Chesapeake City on Rover, so you’re sure to find the perfect match for your dog! In Chesapeake City, 92% of sitters offer daily exercise, 95% offer medication administration, and 97% 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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