Doggy Day Care in Chestertown
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
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Top rated Chestertown doggy day care sitters
“Jen did a great job watching our greyhound Cleo! We had a very last minute need as we moved homes and Jen made it happen. We loved getting the photo updates of how Cleo was doing.”
“Theresa was awesome with my pup. She made me feel at ease with leaving my dog with someone for the first time. Knowledgeable, Friendly, and pleasant to the both of us. I highly recommend Theresa to care for your dogs.”
“Frosty was having separation anxiety and Vince and his mom helped Frosty to calm down. Thank you for taking such great care of him! I definitely recommend Vince as a dog-sitter and I’m already planning on rebooking him sometime this month.”
“Cait (Dax and Daisy) were a delight to work with. Prompt communication and attention to detail regarding our Shih Tzu Tucker was on the agenda. Pictures were send and a quick text message provided the extra comfort that our pup was being cared for and having fun! You can tell Cait is a try pet lover. I look forward to our next event in the area so Tucker can visit again. Thank you so much for adding to a great weekend! Tucker sends his love.”
“Angelene does such an awesome job for doggie daycare! My Bailey loves spending her days with Angelene while I'm working. I love getting pictures during the day of Bailey having a good time!! I highly recommend Angelene!!”
“Briyonna energy is great, she very kind and easy to socialize with. Buddy come back happy, and I will book her again. She seem very prepared and know what she is doing when buddy arrive. I'm very happy with her service definitely book her in future and recommand her.”
“Katie is amazing! This was the first time I left my puppy with anyone. She sent pictures and updates all day. Winston had a blast. He can’t wait to come back tomorrow ?”
“my pup was so excited to see paris again! as soon as we turned down her street for drop off, his tail had already started wagging. i know he’s in great hands when he’s with paris!”
“Our Pup had a great time at Shanon's. He enjoyed the company of her older dogs. Her backyard is fenced, huge, and safe. Very good at communication, and we received updates with pictures. Shanon listened to us on our specific instructions and followed them. She always responded timely to our texts. Fed the pup on time and also arranged a cozy bed for him. We recommend her and would definitely book again when in the area.”
About: I am a dog Mom to two small, adorable rescue dogs! Cooper is a chihuahua mix, 12 years old and 16lbs. Jam is a Maltese mix, 14 years old and 9lbs. They are both males and neutered. I treat them as if they were my children so I would do the same for your dog. I am a stay at home mom and wife with an 6 year old boy. We have a large fenced in yard and can also do walks in our neighborhood. I prefer to watch only small dogs as my dogs get along best with dogs their size. My dogs are allowed on the couch and also sleep in bed with us. I have separation anxiety when leaving my dogs with someone else so I would do my best to ease your anxiety of being away from your dog. I can send you as many daily pictures and updates as you want so you have peace of mind while being away from your dog(s). I can also watch your pets in your home while you are away so your dog can stay in the comfort of their home. I am available for drop ins and can also do daycare sitting in my home. Any questions, please ask! I’m currently a stay at home mom so I can adapt to any needs and schedule for your dogs. I occasionally run errands (grocery store, baseball practice) but otherwise I am home most of the time. I have a fenced in yard and can provide leashed walks as needed. If your dog is not crated when you’re away, it can be the same at my home. I can separate my dogs from yours when I’m not home if needed.
“Bridget was a very good sitter for my fur baby. She was on time on point showed lots of care and love. I really appreciate her help. She is great. Kept in touch with me all day. I’ve really appreciate all that she did. She is amazing.”
About: I've been around animals as long as I can remember. I currently have a puppy named Star and three cats Persephone (Purrsi), Odin and Loki. I foster for the local QA shelter and have worked in a vets office for a short time. I am lucky enough to work out of my house or remote so I am available seven days a week with enough notice. I can come to you or provide care in my house. I live in an end unit Duplex. I have a fenced in yard complete with a puppy pool and beds for lounging. I can provide care in my home or come to yours. Following directions and care requests provided is not a problem.
About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.
Loving doggy day care in your neighborhood
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Jen C.Star Sitter
“Jen did a great job watching our greyhound Cleo! We had a very last minute need as we moved homes and Jen made it happen. We loved getting the photo updates of how Cleo was doing.”
Theresa C.Star Sitter
“Theresa was awesome with my pup. She made me feel at ease with leaving my dog with someone for the first time. Knowledgeable, Friendly, and pleasant to the both of us. I highly recommend Theresa to care for your dogs.”
Vince P.
“Frosty was having separation anxiety and Vince and his mom helped Frosty to calm down. Thank you for taking such great care of him! I definitely recommend Vince as a dog-sitter and I’m already planning on rebooking him sometime this month.”
Cait B.Star Sitter
“Cait (Dax and Daisy) were a delight to work with. Prompt communication and attention to detail regarding our Shih Tzu Tucker was on the agenda. Pictures were send and a quick text message provided the extra comfort that our pup was being cared for and having fun! You can tell Cait is a try pet lover. I look forward to our next event in the area so Tucker can visit again. Thank you so much for adding to a great weekend! Tucker sends his love.”
Angelene H.
“Angelene does such an awesome job for doggie daycare! My Bailey loves spending her days with Angelene while I'm working. I love getting pictures during the day of Bailey having a good time!! I highly recommend Angelene!!”
Briyonna E.Star Sitter
“Briyonna energy is great, she very kind and easy to socialize with. Buddy come back happy, and I will book her again. She seem very prepared and know what she is doing when buddy arrive. I'm very happy with her service definitely book her in future and recommand her.”
Nathaniel G.
“Nate was FANTASTIC. My dog loved being with him. He’s very attentive and communicates great. Extremely happy with Nate, highly recommend”
Ryan P.Star Sitter
“What a wonderful find!!! Such wonderful, caring people! I know my pup is in great care while here! Lots of playtime and individual care too! Highly recommend 🐾🐾🐾”
Katie M.Star Sitter
“Katie is amazing! This was the first time I left my puppy with anyone. She sent pictures and updates all day. Winston had a blast. He can’t wait to come back tomorrow ?”
Briana & Isaiah S.Star Sitter
“Luc always enjoys staying with Briana and Isaiah and their kids!”
Paris V S.Star Sitter
“my pup was so excited to see paris again! as soon as we turned down her street for drop off, his tail had already started wagging. i know he’s in great hands when he’s with paris!”
Shannon S.
“Our Pup had a great time at Shanon's. He enjoyed the company of her older dogs. Her backyard is fenced, huge, and safe. Very good at communication, and we received updates with pictures. Shanon listened to us on our specific instructions and followed them. She always responded timely to our texts. Fed the pup on time and also arranged a cozy bed for him. We recommend her and would definitely book again when in the area.”
Alessandra G.
“Alessandra and family are great sitters! Lots of updates and photos throughout my dog’s stay.”
Stacey B.
“My dog Scout gets so excited every time he sees Stacey! Stacey is very sweet and caring to Scout! She walks him, plays with him and gives him the attention he needs when I’m away! She also sends me pictures because she knows I’m missing my baby! Stacey is someone I highly trust and definitely recommend if you are looking for someone who will take care of your dog like it’s her own!”
Bridget F.Star Sitter
“Bridget was a very good sitter for my fur baby. She was on time on point showed lots of care and love. I really appreciate her help. She is great. Kept in touch with me all day. I’ve really appreciate all that she did. She is amazing.”
Melanie S.
“Melanie was awesome. She sent pictures and took Hutchinson on walks… He was completely tuckered out and had a good time!”
Elizabeth W.
“Ashley W is the best. I have 2 active large dogs, Maisie (6 years old) and Petey (7 years old), who she has taken care of since they were puppies. She has been there for learning manners, leash training, zoomies, park play time, and overnight stays. My dogs absolutely love her and look forward to more playtime with her. She is always on time, communicates with me about all the details, and makes sure my babies are well cared for while I'm gone. I never worry about my pups while they are with her. I highly recommend Ashley W.”
Katharine D.
“Thanks for giving our girl a try!”
Kashya J.
About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.
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Doggy Day Care FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Chestertown on Rover as of Aug 2025 was about $35 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Aug 2025, 201 sitters provided doggy day care in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care 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, 92% of Chestertown sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Chestertown have an average of 18 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 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.
Chestertown doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Chestertown sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:
- Puppies and high-energy dogs
- Dogs with special needs, including seniors
- Pet parents who work long hours
- Dogs with separation anxiety
There are 201 sitters offering doggy day care in Chestertown on Rover, so you’re sure to find the perfect match for your dog! In Chestertown, 96% of sitters offer daily exercise, 100% offer medication administration, and 92% 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 doggy day care 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 doggy day care 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 doggy day care 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 doggy day care 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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