Dog Boarding in Chestertown
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Chestertown dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our pup is always so happy at Michelle’s house! Michelle takes great care of her and sends updates nightly. Stormi is allowed to rule the house when at Michelle’s and definitely feels at home. I love that she is so familiar with cavaliers. Thank you Michelle!”
“Danielle took great care of my dog while I was away! Sadie was happy and well cared for when I picked her up. Danielle was responsive and sent me regular updates so I knew Sadie was happy and safe. I highly recommend Danielle!!”
“Oak really enjoyed her stay with Lindsay! She particularly enjoyed her kiddos! Lindsay made the pickup and drop off logistics incredibly easy! I really appreciated her flexibility. Thanks again Lindsay!”
“Carlie was an excellent sitter, and offered us so much peace of mind while we were away. We couldn't have asked for more! We received daily updates, and our dog was so happy in every photo. The care she received was above and beyond, Carlie even helped adjust our dogs collar and gave her a brushing! I highly recommend booking w Carlie, you will feel like your dog is staying with family - 0 worries!”
“Shuling was fantastic! I was very nervous to have my pup Miso puppy sat for the first time, but I needed a sitter for the holiday weekend, with very short notice. Shuling said yes immediately, and allowed me to come and meet her and her sweet pup Bear that same day. She really put me at ease. She kept Miso for 3 nights and sent several photos twice per day. I never had to worry at all. I can’t thank you enough, Shuling! Miso would love to come and hang out with you again sometime soon!”
“We LOVE Paris!!! Teddy LOVES Paris!!! This was our first time leaving our fur-baby for a 7 day cruise. Paris sent videos and pics throughout the week. I was always informed and felt included. Teddy was wonderfully spoiled by Paris and her husband and he ENJOYED himself. We are already planning another trip knowing that Teddy will be well well cared for!!!”
“Jill and Chad were great with Willie. They sent daily updates and pictures letting us know how he was doing. He definitely got plenty of love and attention while we were away.”
“Our dog Alden had his first visit with Elaine today. We always have a hard time when leaving him, but throughout the day Elaine sent us progress pictures of Alden playing and having a great time. She took such great care of him. Alden looks forward to his next visit!”
“Theresa helped us feel comfortable leaving Louis for the weekend while we travelled out of state. She was warm and friendly when we met and she made friends with Louis right away. She asked thoughtful questions about him and gave us the confidence that he'd be ok. He loved her so much he sat at the back door waiting for her to come back after she dropped him off! 💜”
“As always, Trixie came home tired and, most importantly, happy. Jenn and her husband do a fabulous job welcoming pups into their dog proof home. I also really appreciate the pickup/drop-off amenity. Will definitely use again”
“As someone who is crazy about their dog, I can say I highly recommend Al! Communication and care was great. And he provided lots of cute pics of my pup! Would definitely book with him again!”
“Ran into a need of a last minute sitter for a night, had quick response time of being able to watch my dog. When I picked her up the next morning she was a happy and sleepy girl!”
“Pat and Bee are A+ sitters. They provide daily updates, pictures and videos throughout the stay. Each time our dog has stayed with them she has come home happy and well cared for. Highly recommend and will book again.”
“We loved having Gina watch our dog, Camden. She sent lots of pictures and videos which made us feel so comfortable. He’s been sleeping ever since we picked him up so I know he had a great time! Would definitely rebook with her and highly recommend.”
“Very smooth experience and great stay! They were very kind to our older beagle and he got along well with their dog so everyone was happy. We appreciate it!”
“Justine was great. She has lots of experience, and a bunch of energetic playmate pups! I appreciated the quick drop-off/pick-up without a hassle. She’s quick to respond and sent pictures throughout the day.”
“Barbra is the only sitter I trust to look after my senior dog when I go away. She sends amazing pictures and is great at keeping communication open. 10/10 everytime!”
Over 27 pet parents in Chestertown have booked dog boarding
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1. Search
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3. Book & Pay
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The median cost per night for dog boarding in Chestertown is $45
Why Choose Rover?
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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 Chestertown average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Feb 2026, the median cost of dog boarding in Chestertown is $45 per night, including service fees. Boarding your dog for one week typically costs $315. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chestertown dog boarding rates can be found as low as $25 to as high as $49 per night.
As of Feb 2026, 269 sitters provided dog boarding in Chestertown. 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 Chestertown dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chestertown have an average of 18 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 Chestertown.
Rover makes it easy to find Chestertown 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 269 dog boarding sitters in Chestertown on Rover, so you’re sure to find the perfect match for your dog! In Chestertown, 97% of sitters offer daily exercise, 100% offer medication administration, and 89% 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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