Doggy Day Care Chestertown
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 1 pet parents in Chestertown have booked doggy day care
Chestertown, Find top rated doggy day care
Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our golden retriever puppy, Loki had the BEST time in Tarina’s care! He was extremely comfortable there and was treated like part of the family. We are excited to have Tarina watch him again soon! :)”
“this was my first time using paris & she was amazing!! so friendly, responsive, and kept me updated on my pup all day with great pictures. my pup had so much fun playing with the other dogs. i will definitely be booking again real soon.”
“Omg I cannot say enough good things about Brittney…first off her place is such an amazing doggy heaven, from the large fenced in yard to the pool it is all so dog friendly…Brittney is amazing with the dogs and mine felt right at home with her and at her place ….i cannot recommend her enough…trust me your dog will love spending time at Brittney’s farm”
“We have a last minute drop off and Katie is very responsive and helped us taking care of our baby Raka. We can tell Katie is a dog lover! Thank you again for having Raka!”
“Trishelle was great! I’ve been nervous leaving KB with other people as I’ve had both good and bad experiences on Rover, but since Trishelle also has a dachshund, I thought this would be a great fit and opportunity for KB to socialize. Trishelle is very communicative, keeping me updated throughout thr day, sending pictures and videos. Her dachshund, Ollie was super excited to meet KB, which is great but KB is a bit shy in the beginning. By the time I picked him up, they were playing walking side by side and KB looked right at home! I would definitely recommend Trishelle to anyone looking for a sitter, and will look to book with her again!”
“Mary was great, she just incorporated Allie into her family and daily life. She sent photos of Allie totally chilling out and interacting with people. It made me feel better knowing she was safe and content. I could see that in her face and body language.”
About: ***drop off and pick up times are between 9 am -2:30 pm or between 5 pm and 10 pm***** as I have zoom meetings in mornings and afternoons ; Rover will not let me put in specific times I do apologize****I have two fur babies of my own! They are spoiled rotten. Their names are Rainy and Stormy . I am well trained in giving oral medications as I had a fur baby that had congestive heart failure for 4 years whom also was a senior dog when he passed at 18 years old. I have taken care of other people’s dogs and cats. Where they are treated like my babies while here as well and get spoiled and lots of attention. I work from home and care for my grandmother so I will home with them at all times. I can administrate pills/medicine if needed. I am able to take the dogs out whenever it is needed. My babies are always by my side like shadows. I have a fenced in yard.My dogs love to play with friends dogs. The more the merrier!
“Joyce was amazing. I contacted her super last minute because I wasn’t feeling well and she came to my rescue and took good care of my puppy Houston. He came home so happy and energetic. I received videos while he was in her care and he had so much fun.”
“I have used Michelle for both of my dogs, yesterday was her first time watching my 3 month old yorkie & she did a wonderful job. She made sure he was comfortable because he was afraid at first. I really appreciate Michelle for all of her help. I highly recommend her to anyone needing pet sitting services.”
About: I have walking experience cleaning up after pet playing or just hanging out with them whatever they are in the mood for.your pet will be the main focus for my visit This is my primary focus at this time so my schedule is pretty open for availability.i can also help with special requests if needed . I would like to meet the owners to make sure I am a good fit but I will listen and take notes on everything needed or expected for their furry friend
About: I have been walking/sitting all sized dogs for 10+ years simply because dogs make me happier than anything else! I consider myself affordable so you can work away from home with ease knowing your dog won't be in a kennel all day long! I also dog sit/house sit if you need to go away for business or vacation and can not take your 4 legged friends with you. I am trustworhty and dependable so you do not have to worry about a stranger coming in for your dog but more so your dogs BFF coming in to let the out for a little and play and to use the bathroom for a potty break! I hope to talk to you soon and meet your furry friend(s)! I am home almost all day everyday so my schedule is pretty open and I am extremely flexible to accommodate your schedule as well if needed! I have a fenced in big back yard and a very friendly 3 year old lab to accompany your dog! Frequent let outs and frequent cuddle seshs!
“Emma was so sweet with Puddin' - just the kind of energy that makes my nervous standard comfortable. She was also very flexible with me as I needed to drop off Puddin' way later than originally planned.”
“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.”
The median cost per day for doggy day care in Chestertown is $37
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer doggy day care
2. Meet In Person
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3. Book & Pay
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Popular requests for doggy day care - Chestertown
Select a filter and find qualifying sitters offering doggy day care.Sitters in Chestertown average 4 repeat doggy day care clients
FAQs for Doggy Day Care - Chestertown
Frequently asked questions about Rover
The average cost for Doggy Day Care in Chestertown on Rover is $33.3 per day (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Doggy Day Care easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Doggy Day Care. For more information on service fees, click here .
As of September 2026, there are 1,019 sitters on Rover offering Doggy Day Care across Chestertown. Enter your ZIP code to see which available sitters are closest to your home.
Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Chestertown commute.
If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.
Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.
A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.
Here are tips for finding the ideal day care fit for your dog:
- For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
- For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
- For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.
Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 1,019 sitters in Chestertown, 90% respond to messages in under an hour.
You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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