Doggy Day Care in Chilmark
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 Chilmark doggy day care sitters
“Kayla took our last minute request for a sitter so we could enjoy our day on the vineyard. She was wonderful! Very responsive, prompt and took really good care of our puppy. I’d use her again in a heartbeat.”
About: I’ve taken care of Bernese mountain dogs my entire life, love walking and love walking dogs even more! Huge fan of all breeds and experienced boarding friends and family members dogs. Knowledgable of bondsing with dogs and light training. I work from home so have plenty of time to walk, pet, feed and let out dogs between meetings into the yard. Have plenty of experience with wild dogs, old lazy ones and scared dogs, too. I have a fenced yard and constantly check on dogs even just to pet them because how could you not want to. Have crates and plenty of treats, bowls and dog supplies
“Rachel and her husband were great :) a huge help watching our Bailey during the last day of Beach Road Weekend. She took bailey for 2 shoreside walks near her house. Bailey was all butt wiggles when we dropped her off, definitely sensed a kind dog family and she was right :) Highly recommend!”
“I highly recommend Julia and Bryan. I recently started a new job, and they were able to accommodate my schedule to provide daycare for my dog. They are very responsive to messages and took great care of my dog. They sent photos throughout the day too!”
“Daniella sent photos during the stay and messages to update me on how my nervous dog was relaxing. I was probably more nervous than the dog so I appreciated it! Already have plans to leave my pups with her again.”
“We needed a Last minute option to put our dog for a few hours so we could do a last beach day on vacation . Megan reached back out to us right away ! She was super nice and her yard was beautiful and spacious for ranger to play while we were gone for a few hours .. we will definitely contact her for the future when in the area with our dog . Thank you Megan !!! Rover was great and led us to Megan !”
“Laurel was a fantastic sitter for our dog Ollie. She came home happy, tired, and ready to sleep. Laurel is also a great communicator and responds very quickly. She was also very accommodating to our drop off and pick up time. Highly recommend!! Thanks Laurel!!”
About: As a recent college graduate working remotely from home, I’m looking for a dog fix while also helping those who need a break! I’ve grown up with a Chocolate Lab and a Rat Terrier which gave me various experience with little dogs and big dogs. Unfortunately they are not with us anymore which made me want to pick this up on the side! Remote every week day, except Wednesdays. Will be able to give care at any point in day/night except for my 30 minute meetings 3x per week. I have a big room in my office where the dog can play while I work, they will never be alone. The room has lots of natural sunlight and leads into a big backyard!
“Kathy was amazing with our dog Jax. My baby girl was having surgery in Boston and she put my mind at ease taking great care of our pup. Sent lots of updates and pictures throughout the day which made us super happy! Can’t wait to bring Jax back for another visit!”
About: I've always had both dogs and cats since I was little. Both my sweet kitties needed medication their entire life so I have experience administrating medication if needed. I'm usually my friends go to choice for a dog walker, feeder and pet sitter for long trips during the summer due to my teacher schedule. I currently am only avaliable on weekends as I work full time but I will be avaliable during week days starting in July. During that time, I will have availability for weekends and weekdays. You know your pet best! Before any services, I like to ask questions on your pets daily routine, medications, behavior and feeding routine. This is so I can provide the best care possible for your pet!
“Rebeka is very sweet. Marshall was nervous going to a new place but she sat with him and cuddled with him, which is exactly what works. She was responsive and professional with all communication and we highly recommend her! Marshall had adjusted and was happy by the time we came to pick him up.”
About: Hello, my name is Christine, I am a dedicated pet sitter committed to making your pup feel love and safe in my home. I provide a nurturing environment where your pup can relax and enjoy personalized care, including daily walks, scheduled feeding times and playtime in my fenced backyard. Your pups comfort and happiness is my top priority, look forward to meeting you both! I’m currently working part-time and have plenty of time to walk or roam around the dog park on most mornings and evenings or weekends available. At my home, I have a fenced in yard with plenty of space to roam around. Zoe the labradoodle will keep your pup company during their stay here.
About: I have trained, and cared for dogs for my entire adult life. My wife and I have chosen to adopt some of the dogs that had harder times finding homes; senior dogs, dogs requiring medical care, high energy dogs, so we're happy to care for your animal, quirks and all. I can take care of your pets in your home, I am always up for taking them on a trail walk, neighborhood walk, or beach walk when the season/timing allows. And we are able to host pets in our home. We have an indoor kennel space for dogs, a fenced in yard, and they can play with our 3 lab mixes, or not, as you prefer. I work from home, and take care of the kids and pets throughout the day so I am able to pop over to where your pet is, on island, or care for them in home. I am happy to come to your home, where your pet is most comfortable. We also have a fenced in yard, with indoor kennel space
About: Pet care has always been a part of my life. I’ve raised and cared for dogs, cats, birds, and fish—from puppies and kittens to older pets who need a little extra patience and attention. I’ve experienced every stage of an animal’s life, so I know how to give the right kind of care, whether that means playtime, training support, or simply quiet companionship. What makes my service unique is that it’s a team effort—my girlfriend, Laurel, and I work together to provide care. She’s just as passionate and experienced with animals, so your pet gets the attention of two loving and responsible sitters. We love going on walks in the woods and beach right next to our house, keeping pets active and happy, and making sure they feel safe and loved while you’re away. Pet care is a natural part of our daily routine. I work remotely from home, which gives me the flexibility to be present and attentive throughout the day. My girlfriend is also free for the summer, so between the two of us, your pet will have round-the-clock care and company. We truly enjoy being around animals—walks, playtime, chilling, we love to do it all! Caring for pets isn’t something we squeeze into our day—it is our day, and we love every minute of it! In our home, pets have plenty of space to feel comfortable and safe. We live in a large house with lots of room to play and relax, and we also have a fenced-in area in the yard where dogs can enjoy outdoor time securely. Whether it’s indoor cuddles or supervised play outside, we make sure pets get a great mix of exercise, attention, and rest. We keep a calm, pet-friendly environment and follow each pet’s routine closely—feeding schedules, walk times, and any special care instructions. Our goal is to make them feel right at home, whether they’re staying with us or we’re visiting them in theirs.
About: My wife and I have taken care of dogs and cats our entire lives. We currently share our home with, Bailey, our 5 year old playful mutt. We love all animals and look forward to meeting and caring for new animal friends. We also have extensive experience caring for farm animals, including horses, cows, goats, chickens, etc. We work from home and generally can adjust our schedules in order to accommodate your pets' needs. We will gladly hang out with you pet and give them all the attention they deserve throughout the day. We own our home and have a fenced in private yard. Bailey loves to play but if your pet isn't into her, we get it and can separate them if needed. Our home has plenty of room for everyone to be safe and comfortable. My wife works from home most week days and I work from home part time. We are available to supervise your pet, provide frequent outside time, and play. Bailey will also keep them company. We will treat your animal as part of the family. We want to make sure they are happy and comfortable throughout their stay. They will never be left alone with my dog unsupervised as we want to keep everyone safe. We will always keep your pet leashed when outside of our fenced in yard.
About: Over 20 years of experience with pets- I trained my very first dog at only 10 years old! I grew up with a Great Pyrenees and am experienced with large / xl breeds. I absolutely love dogs and animals in general. I have two precious dogs of my own currently who I love more than anything. I’d be thrilled to care for your dog! I work remotely full time as a software engineer! Your pets are welcome to hang out with us for the day when you’re busy. Weekends I can provide even more active care since I have the days off. I have a fenced in yard but depending on your pets needs I can take them out on leash still. I let the dogs out to play frequently, every 2-4 hours.
About: With my 12 years of experience around dogs and currently working with 25-40 dogs at a dog daycare I can assure you the safety of your furry friend. With a cozy quiet living area and a spacious back yard to stretch their four legs I guarantee your dog will feel at home. Rest without stress at Greys Arcade! Pet care is my life. I do this full time and am available at all times for your pets needs. Running late no problem I will be here. Want to stay on vacation an extra day don’t worry about it I will ALWAYS be here. I have a spacious fenced in yard for outdoor activities and indoor living areas for your pup to feel at home. I have 5 other dogs that are my own that can either give your fur baby company or if your dog dosent like company that is fine to. I have crates of my own if you would want your dog separated from the pack if you choose to.
“Sam was great for our two goldens! Sam and his wife were kind from the get go and accepted both dogs into their house with open arms. We would certainly book again with them!”
Loving doggy day care in your neighborhood
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Kayla J.
“Kayla took our last minute request for a sitter so we could enjoy our day on the vineyard. She was wonderful! Very responsive, prompt and took really good care of our puppy. I’d use her again in a heartbeat.”
Shane M.
About: I’ve taken care of Bernese mountain dogs my entire life, love walking and love walking dogs even more! Huge fan of all breeds and experienced boarding friends and family members dogs. Knowledgable of bondsing with dogs and light training. I work from home so have plenty of time to walk, pet, feed and let out dogs between meetings into the yard. Have plenty of experience with wild dogs, old lazy ones and scared dogs, too. I have a fenced yard and constantly check on dogs even just to pet them because how could you not want to. Have crates and plenty of treats, bowls and dog supplies
Rachel R.
“Rachel and her husband were great :) a huge help watching our Bailey during the last day of Beach Road Weekend. She took bailey for 2 shoreside walks near her house. Bailey was all butt wiggles when we dropped her off, definitely sensed a kind dog family and she was right :) Highly recommend!”
Julia & Bryan M.
Star Sitter
“I highly recommend Julia and Bryan. I recently started a new job, and they were able to accommodate my schedule to provide daycare for my dog. They are very responsive to messages and took great care of my dog. They sent photos throughout the day too!”
Daniella A.
“Daniella sent photos during the stay and messages to update me on how my nervous dog was relaxing. I was probably more nervous than the dog so I appreciated it! Already have plans to leave my pups with her again.”
Megan W.Star Sitter
“We needed a Last minute option to put our dog for a few hours so we could do a last beach day on vacation . Megan reached back out to us right away ! She was super nice and her yard was beautiful and spacious for ranger to play while we were gone for a few hours .. we will definitely contact her for the future when in the area with our dog . Thank you Megan !!! Rover was great and led us to Megan !”
Kathleen R.Star Sitter
“Kathleen was amazing and accommodated everything we needed very last minute for Tucker. She was very responsive and communicable and we enjoyed working with her!”
Laurel K.
“Laurel was a fantastic sitter for our dog Ollie. She came home happy, tired, and ready to sleep. Laurel is also a great communicator and responds very quickly. She was also very accommodating to our drop off and pick up time. Highly recommend!! Thanks Laurel!!”
Thomas S.
“Tommy has been amazing with my 3 year old golden Gus. He goes for runs/walks with him and Gus is a very nervous boy but he is so comfortable with Tommy. Tommy had him for the whole day recently and it was amazing to be able to not worry and know that he is in good hands!! Tommy is very responsive as well and is always willing to help. Highly recommend!”
Kathleen W.Star Sitter
“Kathy was amazing with our dog Jax. My baby girl was having surgery in Boston and she put my mind at ease taking great care of our pup. Sent lots of updates and pictures throughout the day which made us super happy! Can’t wait to bring Jax back for another visit!”
Alexis F.
About: I've always had both dogs and cats since I was little. Both my sweet kitties needed medication their entire life so I have experience administrating medication if needed. I'm usually my friends go to choice for a dog walker, feeder and pet sitter for long trips during the summer due to my teacher schedule. I currently am only avaliable on weekends as I work full time but I will be avaliable during week days starting in July. During that time, I will have availability for weekends and weekdays. You know your pet best! Before any services, I like to ask questions on your pets daily routine, medications, behavior and feeding routine. This is so I can provide the best care possible for your pet!
Michelle C.Star Sitter
“Bonnie was excited to go spend the day with Michelle and Winter every day! I was grateful that Michelle loved my pup while I was in town for work.”
Rebekah C.
“Rebeka is very sweet. Marshall was nervous going to a new place but she sat with him and cuddled with him, which is exactly what works. She was responsive and professional with all communication and we highly recommend her! Marshall had adjusted and was happy by the time we came to pick him up.”
Christine T.
“Christine has been a fabulous dog walker and pet sitter. She is completely reliable, very friendly, and takes great care of my dog. And the bonus is that she has a wonderful family including two boys who help out with walking and playing with the dogs. My dog is so happy when he sees Christine, and he loves going to her house for overnights. I know he has a great time and is very well cared for when he's there.”
Marc A.
“Marc has taken care of my pets for many years, he always prioritizes the care of pets above all else. He is very capable with any size animal, and is smart about dog needs if they need space and awareness when walking by other dogs, noticing stress signals, deescalating any challenging situations between pets.”
Emmanuel & Laurel P.
“I can confidently say Emmanuel would make an amazing dog sitter! He’s always been incredibly caring, responsible, and patient—qualities that naturally extend to the way he interacts with animals. I’ve seen how gentle and attentive he is with dogs, whether they’re his own or someone else’s. He’s the kind of person who goes out of his way to make sure others (including pets!) feel comfortable and cared for. If you’re looking for someone who will treat your dog like family, Emmanuel is that person!”
Peter & Michelle P.
“Peter and his wife are huge animal lovers. He is kind and responsible and will do anything for his own animals or to help animals in need. I would trust him 100% with my furry loved ones.”
Clara M.
“Clara is an extremely responsible person who truly cares for animals. She has been watching my dogs for years and they're always happy to see her. I don't ever worry about my dogs when she's watching them because I know they're safe and in the best hands.”
Austin C.
“Austin C has taken care of not just his pets but mine as well he is great at tending to their care and just overall a great person you’d want to watch your pets. He works at a doggie daycare as the daycare manager and has worked there for 2 years. He is very experienced and knows what he’s doing. I definitely recommend!”
Sam M.Star Sitter
“Sam was great for our two goldens! Sam and his wife were kind from the get go and accepted both dogs into their house with open arms. We would certainly book again with them!”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter 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!
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
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 Chilmark on Rover as of Aug 2025 was about $41 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, 74 sitters provided doggy day care in Chilmark. 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, 83% of Chilmark sitters offering doggy day care respond in under an hour.
Sitters offering doggy day care with repeat customers have an average of 6 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 Chilmark.
Chilmark 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 Chilmark 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 74 sitters offering doggy day care in Chilmark on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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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