Dog Boarding Chilmark
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Chilmark, Find top rated dog boarding
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Total rock star sitter - could not recommend Kari any more highly! This was only Sadie‘s second time boarding in someone else’s home without me…I learned from my first experience that Sadie does not do great with other pets in the house… and, even though Kari’s was pet free, I was still trepidatious about trying another boarding situation in a strange (to my pup) home. My fears were immediately alleviated upon meeting and seeing Kari interact with Sadie and how she let Sadie explore around her wonderful home. Physical relief was all I felt when I left Sadie with her. Kari kept me informed each day with reports and pictures of what she and Sadie were doing, and I was never worried that Sadie was anxious or anything but completely comfortable. Seriously will make sure that Kari is available anytime I plan anything where I need to leave Sadie with someone for any reason! I think my girl had a great time and definitely was very well cared for. Cannot thank Kari and her family enough! ❤️❤️❤️”
“Melissa is AWESOME! Jagger always has a blast. He runs right to her when she picks him up. I feel very comfortable knowing Jagger is with her, safe, and having so much fun!!!”
“Mike was recommended to me from a coworker who raved about him! I can see why- my dog was VERY HAPPY with his stay- they sent me pictures so I could see how comfortable he was with them!”
“Kayla was amazing! She helped me out when I was in a pinch and was available the day before I had to leave. Drop off and pick up was easy. I would definitely choose Kayla to watch my pup in the future! ❤️”
“Ruby was wonderful with our dog, Moose. We were able to leave town and not worry about him. She also sent us some great photos and videos of Moose playing with other dogs in her care. I highly recommend her!”
“Fantastic dog sitter! She is compassionate and takes fantastic care of your pet. My dog was happy and comfortable the entire time she was away and the level of care is even better than a professional facility. She even sends daily pictures and videos and that is great when missing your pup. Next time I need to leave my dog I will definitely be sending her back over Nathalias!!”
About: I am a lifelong dog lover with hands on foster experience and a deep passion for giving every pup a safe, happy home. Whether I am helping a nervous rescue decompress or welcoming a high-energy playmate into my routine, my background in fostering has taught me patience, adaptability, and how to read a dog's unique body language. Dogs are my absolute world, and I bring that same fierce, nurturing love to every dog I care for. At home, my beloved dog, Molly, shares my passion for making new canine friends and helps keep our space warm and welcoming. Your furry family member will be treated with the exact same devotion, safety, and endless belly rubs that I give to Molly. Thank you:) ! I just started a nursing program that is mostly online, so I am home and ready to keep someone's pup good company! I am flexible, can come to you if needed, and very easy going when it comes to walks and other needs you may have! Welcome to my home, where your dog will find a safe, trustworthy environment built on constant companionship and love. While I do not have a fenced-in yard, your dog will never be left to wander alone; instead, they will have a dedicated sitter to supervise, watch, and play with them every moment they are here. I treat every guest like a member of my own family, ensuring they get plenty of supervised outdoor exercise, interactive playtime, and continuous attention. Trust me, attention won't be a problem. You can rest easy knowing that your dog is in reliable hands, surrounded by people who are fully committed to keeping them happy, engaged, and completely secure.
“Our dog seemed very happy to stay at Kevin’s house. We were especially grateful that he could take her in for a last minute reservation and it was nice that he sent pics and videos every day. Also- we appreciated that Kevin arranged a refund for us since we picked up our dog a day earlier than planned. He was quick to respond to texts, and is clearly a very responsible person.”
“Wendy was easy to work with and very responsive. She took care of our dog Atticus like he was her own. Atticus seemed very comfortable with her right away. She was very flexible with pick ups and drop offs. I would recommend her to anyone in the area! We would definitely use her services again.”
“Emily was wonderful to deal with and took good care of Izzy. She sent us photos during Izzy’s stay with her and updates of activity. I was at the Cape for my son’s wedding and I had peace of mind knowing I didn’t have to worry about Izzy and I could just enjoy the weekend. Izzy was happy and her snuggly self when we picked her up. I’ll definitely look to Emily in future for our trips to the cape.”
“100% satisfied with Victoria couldn't ask for any one better to watch my dog. Ty is an 18 year old morkie who requires alot of care he is completely blind and wears a diaper and Victoria went above and beyond with my dog. I knew ty was in good hands with Victoria. I will definitely leave ty with Victoria if I ever need a dog sitter again. Thank you Victoria 😊 10 stars from me ❤️”
“Mary took great care of my fox terrier, Pepper, with many walks and loving care. Her yellow lab is a mellow dog who loves doggie company. I especially appreciated a “meet & greet” beforehand, so Pepper was able to meet Mary & her dog & be familiar with surroundings, so as not to be shocked when I left her this first overnight. Mary’s love for dogs shows.”
“Ann was great! We did a meet and greet ahead of time and communication was great for the overnight. You could tell Philly was comfortable the whole time. Will absolutely book again.”
“These two were amazing!!! They have two small dogs who are welcoming and loved my Roxie. They have a beautiful, fenced in backyard with plenty of shade and room for the dogs to get their energy out. The house was nice and most importantly, Roxie was clearly well cared for with belly rubs and attention as she seemed to not want to leave! I loved that they offered a visit first to make sure it was a good fit and their communication was great while I was gone. Will definitely use again.”
About: I’ve taken care of dogs since I was 15! I’ve had pets all my life growing up though! My neighbors, friends, and family, have relied on me to feed, walk, play, and give cuddles to their pups! I currently am working part time as I just started a new job, so i’ll have plenty of time to play with your pup and get them some exercise! My home has a fenced in dog park that i’m sure your dog would love to run around in and get some energy out! If your dog is better on a leash and loves to walk and sniff around your area I am happy to do that as well! I just want to be able to give your pup a safe and happy visit 😊
About: I’ve cared for cats and volunteered in cat rescue for over 20 years. I have always been the person friends, family, and neighbors trust with their pets. I currently volunteer in animal rescue, where I care for and foster kittens, senior cats, and cats with medical needs, including administering medications and monitoring their health. As a licensed Community Health Worker with over 20 years in healthcare, I bring patience, attention to detail, and reliability to every visit. I know every pet is unique, so I take the time to learn their routines, provide enrichment and affection, and keep owners updated with photos and detailed visit reports. My goal is for you to have complete peace of mind while you’re away. Pet care is currently one of my main priorities, which allows me to offer a flexible schedule and provide pets with the time and attention they deserve. I’m available for morning, afternoon, and evening visits, as well as weekends and many holidays. Whether your pet needs a quick potty break, medication, playtime, or companionship, I strive to keep their routine as consistent and stress-free as possible. I communicate promptly and provide updates and photos after every visit so you always know how your pet is doing. Caring for animals is more than just a job to me—it’s something I’m truly passionate about. I have over 20 years of experience in healthcare, am a licensed Massachusetts Community Health Worker, and volunteer and foster with the MSPCA of Cape Cod and It’s All About the Animals, Rochester where I regularly care for and foster cats of all ages, including those requiring medications and special medical care. I understand how important it is to earn your trust, so I carefully follow every instruction regarding feeding, medications, walks, litter boxes, and household routines. I treat every pet as if they were my own, ensure doors and gates remain secure, and always provide detailed updates with photos so you can feel confident your pet is happy, safe, and well cared for.
“Christine watched my dog for the first time. I felt completely comfortable leaving him for 5 days. She kept me updated with pictures. I picked up a happy boy at the end! Will definitely be using her again.”
About: Hello! I’ve been a dog owner my entire life and am excited to learn more about your pup. I have a very friendly golden retriever who will be home during your dog’s stay and will be around all day to play with your dog and can take them out at regular intervals. Look forward to hearing from you! I’m currently working on from home so I have plenty of time to spend with your dog! I’m up usually around 7am and can take the dog out first thing, then usually take the dogs out around 11pm for a last potty break. I’m very clean/organized and will be respectful of your home and belongings should you need me to stop by your home to watch your pup
The median cost per night for dog boarding in Chilmark is $66
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.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Chilmark
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chilmark average 13 repeat dog boarding clients
FAQs for Dog Boarding - Chilmark
Frequently asked questions about Rover
As of November 2026, there are 184 sitters on Rover offering Dog Boarding across Chilmark. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
96% of sitters in Chilmark can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chilmark home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Chilmark.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Chilmark. On Rover:
- 92% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
You and your Chilmark sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
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.
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 MA 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.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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