Dog Walking Chilmark
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Chilmark, Find top rated dog walking
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: I have been a pet sitter for the last 10 years, working for neighbors as well as for the families I was nannying for. I am committed to the dogs I am caring for and I will treat them as if they are my own. I currently work in a hotel and taking care of animals in my free time would be work that I am very passionate about. I am happy to take the dogs on walks, or host in your home. I currently work part time so I would love to fill my free time caring for animals. I spend most nights on long walks so it would be great to have a companion to keep me company. I am very responsible and trustworthy. I would treat your dog and your home as if it is my own. I am happy to feed, play, walk, go to the beach, or anything that will make the pets happy.
About: I have a lot of pet care experience and can assure you that I will love your animals. I grew up surrounded by animals and have been trusted by my friends, neighbors, and family members to watch their pets and homes. I have long term pet and house sat in Montana, the U.S. Virgin Islands, Alaska, and North Carolina! Feel free to reach out for references or my resume. I’m an early riser, love to go on walks with animals, and have a very flexible schedule. I have been work pet and house sitting this past summer in the U.S. Virgin Islands while holding a few boat jobs as well. I will be in Vineyard Haven for the summer, working on a sailboat, and would love to spend my free time taking care of your animals. My schedule is charter dependent, but is pretty much flexible at this moment! With my flexible schedule, check-in times can be more frequent if they are needed and I am able to provide my full attention to your animals.
About: I have a senior cat with a serious digestive and heart condition, so I’m certainly used to giving pets their proper medications, feeding at specific times, or just generally giving them the love and attention they need! I grew up with dogs, and have pet sat for friends, family and clients for years. I feel more than comfortable feeding, walking or staying with pups of any breed or size. I’ve been a sitter on Trusted Housesitters for years and have been lucky enough to let sit as far away as Berlin! I’d love the opportunity to take great care of your pets while you’re away! I have a super flexible schedule with work and can generally accommodate most days/times. I live on Martha’s Vineyard and can travel most anywhere on island to sit. My fiancé and I are more than happy to accommodate any and all let needs. With our senior cat experience, and lots of daily and overnight sitting experience, we always treat animals with kindness, patience and respect. We will always ensure animals feel comfortable in our care, and we update owners on their pets as much as possible!
“Rachel is an excellent dog walker. She is so kind and compassionate with animals, and was so great with our can-sometimes-be-a-bit-challenging Border Collie! She was wonderful on his daily walks, and took great care of him in our home while we were away. She is smart and responsible and an all-round great person. Highly recommend!”
About: I adore dogs and have been a consistent pet and home sitter for several families on Martha’s Vineyard over the last 8 years. I am tidy, responsible, and take care of pets as if they were my own. I love to take daily long walks (3-5 miles) and the companionship of a dog makes this personal routine so much more fun. It’s not possible for me to have a pup of my own in my current housing so getting to spend time with other dogs brings me so much joy. Work freelance as a henna artist and with a catering company on island. I have a varied work schedule with most mornings open, happy to try to make your pet care needs fit into my day. I’m a great communicator and will always make sure I fully understand the needs of your home and pet before I agree to a job. I want us both to have a clear understanding and expectation of the level of care required so that everyone is comfortable. I am very respectful and mindful that every pet and home is unique, the details matter to me.
About: I bring high-energy, all-terrain enthusiasm to every pet I care for! Whether I’m biking, swimming, running, walking, rollerblading, or scootering, I stay active so your dog can too. I’ve worked with pups of all ages—from playful puppies to mellow seniors—and tailor each walk or visit to fit their pace and personality. Pets aren’t just cared for, they’re engaged and uplifted. Let’s turn walk time into mission time! I work from home full-time, which means I’m always nearby and flexible. Pet care fits naturally into my day—I schedule walks, playtime, and snuggles around my work. I treat every pet like family—whether they're with me or I'm visiting their home. I have a fenced yard for safe outdoor time and two friendly dogs for social play. I follow any special instructions you provide and can crate your pup if needed. Clean spaces, constant supervision, and a whole lot of love ensure your pet’s comfort and security.
About: Beyond being a dog owner myself to my beloved rescue Jordi, I've also taken more dog sitting jobs than I can count. I LOVE dogs! I like to go the extra mile by taking dogs on extra long walks and adventures, always administering their medication at the correct time, giving dogs extra love and cuddles, and always keeping the house super neat and tidy. I already walk my own dog twice a day, and he loves walking with a friend! If you need a drop in visit or occasional help with a dog walk, it's already a part of my routine. Of course I do not need to bring my own dog, but if your dog enjoys the companionship of other dogs, it could be a great option! I am not allowed to have any more pets other than my own where I am currently living so I will not be able to board your dog, only house sit. Thanks for understanding.
About: ***AVAILABLE ON MARTHAS VINEYARD ONLY*** - Intermittently on Nantucket but dates of availability only reflect that of MV. Please inquire with a message for Nantucket :) My experience with animals began as a child both with family pets and horseback riding. Being on the farm at such a young age instilled in me a love for animals that has only grown over the years. It also allowed me a front row seat to better understanding animals and their individual behaviors. Throughout the years, I have become proficient in medication administration and personalized feedings scheduled and requirements. I have also been privileged to be around animals of all kinds and ages and I look forward to providing your young and senior pets with the extra love and attention they require and deserve. In my day to day life I am a licensed and trained paramedic which has helped me better harness the patience and understanding often required when helping animals and their families. For those of you that have pets with boundless energy, I go for a minimum 5 mile walk daily that could only be made better by the accompaniment of your four legged family member. I look forward to meeting you and your perfect pets! I currently work part time as a paramedic which allows for a lot of freedom and flexibility in my schedule to help you and your pet. As I will be watching your pet in the comfort of your home- I will always want to know what helps them adjust to change best in your absence. How can I make them, and you, feel more comfortable? What toys do they love? What types of check ins work best for you and what information do you prefer to be kept up to date on? Does your pet have any health history or allergies? What ever you think will make this experience best for you and your pet is information I would love to be made aware of!
About: Hi there! I’m Brittany, a super fit, energetic animal lover who’s ready to take your furry friend on their next adventure. Whether it’s a brisk walk or a fun run, I’m all about giving your dog the exercise they need! I have a deep passion for animals and always ensure to provide lots of patience and care. Strong communication with pet owners is super important to me, so you can expect regular updates and feedback on how your pet is doing. I am currently working remotely so I have great flexibility to provide care! All I ask is for at least a days notice to properly plan. I look to set up an initial meeting to make sure your pet feels comfortable with me. If all goes well we can discuss further proper care!
About: I’ve taken care of dogs professionally in the last year, throughout that time I was required to take an animal CPR/First Aid course. This was very educational and I believe that anyone working with home pets such as dogs and cats should have this knowledge and ability, so your pets are well taken care of and gives the owner a large amount of relief knowing the person they are with is educated for the safety, and also has so much passion for animals! A side from a professional career, I have been around Dogs as well as Cats my whole life in my own home as well as all of family members always having dogs. At this time I have mornings and afternoon available to attend to your pups needs! Pet Care is very important, and I have a very flexible schedule to make it happen! The services I offer to your pets, is walking and check ins. With this care I will provide a 1-3 mile walk depending on your preference
The median cost per walk for dog walking in Chilmark is $25
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- 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.
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog walking
2. Meet & Greet
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 near you
Select a filter and find qualifying Chilmark sitters!Sitters in Chilmark average 3 repeat dog walking clients
FAQs for Dog Walking - Chilmark
Frequently asked questions about Rover
As of July 2026, there are 608 sitters on Rover offering Dog Walking across Chilmark. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Chilmark. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Chilmark.
Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.
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 walker 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 .
Yes, you can find walkers who have experience with handling special pet needs in Chilmark. On Rover:
- 94% of walkers can help with special care needs
- 94% can help with giving oral medications or injections
- 98% 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.
A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.
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 walker.
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