Dog Boarding in Chestertown
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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.
“I can’t say enough about Gisel and her family that gave us a warm welcome the moment we connected. At our meet and greet, I knew she was the one to host our #furbaby Cody. Even her children were loving towards him. They are a wonderful family and far exceeded our expectations of caring for our Cody with pics and videos the whole seven days. Our neighbor uses her as well for their Yorkie and are very pleased with the care they’ve received. The bonus for us, she’s a stay at home mom and Cody was not left alone all day. She has small dogs as well and he was able to meet new friends. This was our first time leaving Cody without family and Gisel eased all of my anxiety because of her love for animals. We’ll be using her again soon.😊”
“Michelle was very responsive for a last minute booking. She sends an end of the day summary with photos and comes outside to meet you right when you arrive! My boyfriend and I were able to go on our trip without a care in the world knowing that Michelle had our baby tucked away in her loving household. Thank you Michelle, we'll be back!”
“Paris took great care my Deacon and sent me updates of pictures that I adore She was very professional. I will definitely be using Mrs. Paris service again because I was very satisfied”
“i can not even begin to express how wonderful Theresa is. I love to go places, but I always hated leaving my dog (or dogs when I had more than one). Theresa IMMEDIATELY made me feel at ease, as well as my dog. I actually had to google to find a word that could convey how great she was, and I found "cynophile" which is a dog lover, but she is more than that. She not only understands what the dog needs, but also what us pet parents need. She eased my worries, she sent me pictures, she assured me that what I was feeling was normal. I know that I not only had a good time, but my dog enjoyed her vacation as well. You will definitely will make it so much easier to say yes when I am asked if I can get away Thank you Theresa!”
“Shuling was outstanding with her loving care for our 4 year old Venus. She followed our feeding instructions and provided pictures and/or videos daily. The pics showed how happy Venus had adjusted in her home with her dog Bear and other dogs at times. Shuling could be a photographer because she took the best pics. I am so thankful for the loving care Shuling provided for our pup. This was the longest we left Venus and she was well taken care of. I believe Venus is missing her new friend Bear because when I mention his name she gives a positive response. We will definitely use Shuling in the future. I would highly recommend Shuling for anyone considering a dog sitter. Thanks again Shuling and your family!”
“Liz and Eric treated my Fendi like she was one of their own pups. They sent daily pictures AND videos. In many of the pictures it looks like Fendi is smiling. I will not hesitate to contact them should the need arise in the future,”
“My dog loved his stay here! He came back tired and happy. I got lots of pictures of a very happy dog, I can tell he got a lot of love from their whole family and lots of fun playtime.”
“My family and I were in town for a couple of days and we needed a last minute dog sitter. Cait had some good reviews and so we decided to move forward and have her dog sit. She was awesome! Our dog had a great time and Cait said she enjoyed playing with her dogs. If we’re in town again, we would definitely reach out!!”
“Mia had a great time with Jill and Chad's family! Jill sent pictures and updates daily, and administered all of her meds on schedule. I can tell Mia felt right at home with them.”
“Such a nice experience. From the meet and greet to picking up my pups,there was great communication. The pictures gave reassurance of what a great time was being had. I highly recommend.”
“Katelyn provided the most amazing care for our puppy!! He was spoiled with multiple walks, many treats, and tons of snuggles while we were away for a long weekend. He became friends with their sweet husky as well. Can’t wait for him to stay with her family again soon!! Thank you!!”
“She had done greet with our dog lili she is about a year and six months old no issues at all very knowledgeable of dogs in their situations as well as understanding their behavior with no issues she took care of my dog and my dog played with her dog so now my dog has a friend they went to the park together and everything and she bought my dog back, clean safe and sound no issues Thank you very much once again for watching her for the five days. It’s been great. We definitely use her again just for dog play dates. Also she’s amazing. Don’t hesitate.”
“Jen’s the best! Highly recommended her services. It’s a great sign when Piper is super excited when we pull up and doesn’t wanna leave. I know she is in good hands and having a blast!”
“Elizabeth was absolutely amazing with my dog Lucy! She updated me with a video and kept in contact with me. She was also absolutely wonderful at helping with my puppy’s socialization skills. I absolutely recommend and will be using her services again.”
Loving dog boarding sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Gisel D.Star Sitter
“I can’t say enough about Gisel and her family that gave us a warm welcome the moment we connected. At our meet and greet, I knew she was the one to host our #furbaby Cody. Even her children were loving towards him. They are a wonderful family and far exceeded our expectations of caring for our Cody with pics and videos the whole seven days. Our neighbor uses her as well for their Yorkie and are very pleased with the care they’ve received. The bonus for us, she’s a stay at home mom and Cody was not left alone all day. She has small dogs as well and he was able to meet new friends. This was our first time leaving Cody without family and Gisel eased all of my anxiety because of her love for animals. We’ll be using her again soon.😊”
Michelle M.Star Sitter
“Michelle was very responsive for a last minute booking. She sends an end of the day summary with photos and comes outside to meet you right when you arrive! My boyfriend and I were able to go on our trip without a care in the world knowing that Michelle had our baby tucked away in her loving household. Thank you Michelle, we'll be back!”
Paris V S.
Star Sitter
“Paris took great care my Deacon and sent me updates of pictures that I adore She was very professional. I will definitely be using Mrs. Paris service again because I was very satisfied”
Theresa C.Star Sitter
“i can not even begin to express how wonderful Theresa is. I love to go places, but I always hated leaving my dog (or dogs when I had more than one). Theresa IMMEDIATELY made me feel at ease, as well as my dog. I actually had to google to find a word that could convey how great she was, and I found "cynophile" which is a dog lover, but she is more than that. She not only understands what the dog needs, but also what us pet parents need. She eased my worries, she sent me pictures, she assured me that what I was feeling was normal. I know that I not only had a good time, but my dog enjoyed her vacation as well. You will definitely will make it so much easier to say yes when I am asked if I can get away Thank you Theresa!”
Shuling J.Star Sitter
“Shuling was outstanding with her loving care for our 4 year old Venus. She followed our feeding instructions and provided pictures and/or videos daily. The pics showed how happy Venus had adjusted in her home with her dog Bear and other dogs at times. Shuling could be a photographer because she took the best pics. I am so thankful for the loving care Shuling provided for our pup. This was the longest we left Venus and she was well taken care of. I believe Venus is missing her new friend Bear because when I mention his name she gives a positive response. We will definitely use Shuling in the future. I would highly recommend Shuling for anyone considering a dog sitter. Thanks again Shuling and your family!”
Liz & Eric F.Star Sitter
“Liz and Eric treated my Fendi like she was one of their own pups. They sent daily pictures AND videos. In many of the pictures it looks like Fendi is smiling. I will not hesitate to contact them should the need arise in the future,”
Lindsay G.Star Sitter
“My dog loved his stay here! He came back tired and happy. I got lots of pictures of a very happy dog, I can tell he got a lot of love from their whole family and lots of fun playtime.”
Cait B.
“My family and I were in town for a couple of days and we needed a last minute dog sitter. Cait had some good reviews and so we decided to move forward and have her dog sit. She was awesome! Our dog had a great time and Cait said she enjoyed playing with her dogs. If we’re in town again, we would definitely reach out!!”
Jacob & Megan W.Star Sitter
“Jacob and Megan are wonderful sitters. Our two beagles have a blast there. They get plenty of attention and walks as well. I highly recommend”
Jill & Chad H.
“Mia had a great time with Jill and Chad's family! Jill sent pictures and updates daily, and administered all of her meds on schedule. I can tell Mia felt right at home with them.”
Ryan P.Star Sitter
“Such a nice experience. From the meet and greet to picking up my pups,there was great communication. The pictures gave reassurance of what a great time was being had. I highly recommend.”
Katelyn M.Star Sitter
“Katelyn provided the most amazing care for our puppy!! He was spoiled with multiple walks, many treats, and tons of snuggles while we were away for a long weekend. He became friends with their sweet husky as well. Can’t wait for him to stay with her family again soon!! Thank you!!”
Briana & Isaiah S.Star Sitter
“Briana and Isaiah were lovely! They welcomed my dog Steven into their home, and treated him like one of the family. I highly recommend their services 😊”
Elizabeth W.
“I had great peace of mind knowing my dog was in good, kind hands for the day. I got updates that showed he was doing well. Thank you!”
Elizabeth F.Star Sitter
“She had done greet with our dog lili she is about a year and six months old no issues at all very knowledgeable of dogs in their situations as well as understanding their behavior with no issues she took care of my dog and my dog played with her dog so now my dog has a friend they went to the park together and everything and she bought my dog back, clean safe and sound no issues Thank you very much once again for watching her for the five days. It’s been great. We definitely use her again just for dog play dates. Also she’s amazing. Don’t hesitate.”
Gina M.Star Sitter
“Gina is amazing! She clearly loves dogs and sent several pictures and videos. Very communicative and made everything easy. Will definitely book again!”
Jen C.Star Sitter
“Jen’s the best! Highly recommended her services. It’s a great sign when Piper is super excited when we pull up and doesn’t wanna leave. I know she is in good hands and having a blast!”
Katherine B.Star Sitter
“Katherine and her family took wonderful care of our boys. They thoroughly enjoyed their stay and were cere well cared for. The updates and action photos were great.”
Erin I.Star Sitter
“Erin was so good, I was worried about the rain and definitely reasdured me she's got it in hand. Loved how tired Sinatra was upon return, he was definitely a happy pup”
Elizabeth N.
“Elizabeth was absolutely amazing with my dog Lucy! She updated me with a video and kept in contact with me. She was also absolutely wonderful at helping with my puppy’s socialization skills. I absolutely recommend and will be using her services again.”
Over 27 pet parents in Chestertown have booked dog boarding
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Select a filter and find qualifying Chestertown 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
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The median cost per night for dog boarding in Chestertown is $45
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 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 13 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 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 Aug 2025, 260 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 17 years of experience. Dog boarding sitters with repeat customers have an average of 13 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 260 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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