Dog Walking Chestnut Hill
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 67 pet parents in Chestnut Hill have booked dog walking
Chestnut Hill, 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%.
“Gabriel was terrific with our little man (9.5 year old Yorkie poo). Our regular dog walker was on vacation and Gabriel reliably covered 4 days of walks. He is a dog owner himself and a dog lover, and we could tell that he took great care of our dog. He was an excellent communicator and was prompt with his pick up on each of the four days he walked our dog. We would definitely use Gabriel in the future.”
About: Howdy! My name is Natalie and any dog I've met I have loved like my own. Growing up I had my fluffy 90lb Labradoodle and two sweet guinea pigs. Aside from my own pup, neighbors, friends, and family have relied on me to walk and feed their dogs and care for their cats. I currently have a full time job where I have to go into the office Monday-Thursday but an available for walks and drop-in on Friday, Saturday, and Sunday. I live in a small apartment in Brighton MA across the street from a wonderful reservoir and less than a mile away from several parks! I am a very active person so would be a great host for an athletic or active dog! However, if your dog is less active, I can easily bring my activity level to where your dog is happy and comfortable. I allow pets on my bed and couch, unless you prefer them not to.
About: As a lifelong pet lover and daughter of a vet tech, I have lots of experience spending time with and caring for cats and dogs of all ages. All through my life my family has had pets and we often fostered animals, especially kittens and puppies, at my home. As I renter I haven’t been able to have dogs of my own since moving out of my family’s house. Our dogs are the highlight of visiting home and I would love the opportunity to care for your dogs while you are away! I work from home during the day with a very flexible schedule. I could make some visits in the mornings, but I am mostly available in the evenings during the week and all day Friday - Sunday. I might have more time around the holidays, as well. I can also housesit if I have notice since I can work from anywhere. I’m not able to host any pets at my home due to having my own spicy kitties, but I’m happy to housesit or do drop in visits or walks. Let me know what you are looking for and I’m happy to help!
About: I have dog and cat sat for the past 7 years for multiple different families in the Yarmouth Maine area. I have been in different situations that have tested my abilities as a pet sitter. Dogs and cats immediately warm up to me. I currently work a full time job for a Doctor in the Yarmouth area. I can walk dogs after work most of the time. We sometimes don’t work at the office on Fridays so I would be able to walk dogs during the day. I can do overnight care, however I would only be able to feed / walk in the morning and evening before and after work. I am more flexible on weekends. Whenever I am caring for dogs I will keep them on a leash when I walk them. I make sure to follow the clients rules for their pet (feeding, care, and walking routine).
“Leanne has been walking our dog 4 days a week for the past few weeks. She is responsible and shares great info and updates. And Maggie is always so excited when she arrives. Leanne goes above and beyond. We are going to keep using her as long as we can!”
About: I have been a dog Walker and sitter for about 8 years now, and I also have two dogs of my own that I love! I do have a full time job, where I work a hybrid schedule, so I am sometimes able to do mid day walks, evening walks, and also pet sitting over nights on weekends or weekdays. I walk my dogs everyday at least 3 times a day, and when I am dog walking for clients, I will give them as many walks as they need, for at least 20 minutes.
About: I have had dogs my entire life and love dogs more than anything. I'd care for your dog as if it was my own and give it the most love and attention. I have experience walking dogs, house-sitting dogs, playing with them, bathing them, and feeding them. Additionally, I love every dog and wouldn't mind taking care of more than one! Being with dogs is my favorite activity and I would love to help in any way that I can! Your dogs will receive the most love and cuddles and I can’t wait to meet them!
About: Growing up, my family always loved and cared for dogs. We first owned a chocolate lab, Indy, then Maple, a thirteen year old yellow lab. As a teenager, I helped train dogs that would go on to have careers in rescue units, airports, or the WUSV championships. I now own my own dog Dax with my wife Libby, a Chihuahua-Rat terrier mix who loves to show new friends around the neighborhood. (P.S. any Rover friends who know Trang, we are besties!) I know the ins and outs of the pet scene in Boston and where the dogs thrive. I also have a dog that is equally happy to sleep all day as he is to hike and run on the soccer field. Pets have always been a part of my life, and I'm so happy yours will be too! I live on a quiet street to walk the dogs. I also have a private backyard for the dogs to run and play, as well as letting them have free range of the house -- any soft surface is theirs! I love to cuddle up with the dogs as soon as we get home.
About: My family has owned dogs all my life. All of them have been shelties, so I know how to care for energetic dogs. I helped take care of our senior dog Misha, who passed at 17 years old. I also helped train and care for our two puppies Sadie and Ollie. Sadie has anxiety problems, and I’ve had plenty of experience getting her to take medications. She also had to get surgery to remove her tail, and I was her primary care giver during her recovery, including administering medication and cleaning the site. Now that I’ve moved away from home for college, I don’t get to see my dogs much anymore, and would love to care for yours! I’ve also had experience caring for cats, even though I’ve never personally owned any. My best friend used to have 6 cats and I always took care of them when they’d go on vacations, including administering meds, feeding, cleaning litter boxes, and playing. I’m currently working part time and am a student at CU, so I have time to take dogs on walks or drop in to check on them and let them outside. In the summer, my schedule will open up and I’ll be able to pet sit for longer times while you go on vacation! I feel safe around all sorts of dogs, including big ones. I’m not able to have pets in my apartment, but I will provide them with the highest level of care in your home! I will take them on long walks around the neighborhood or to parks.
“Sydney has been amazing for our dogs Myla and Malibu. She is quick to respond, reliable and trustworthy. Our girls love their walks and drop ins from Sydney! Can not recommend someone more!”
About: I grew up with two English Setters and cared for them from their puppy years through their senior stages, giving me hands-on experience with dogs of all ages. I’ve also dog-sat many times for friends and neighbors and have experience walking multiple dogs at once, safely and confidently. I truly love animals and take pride in providing attentive, reliable, and loving care treating every pet like my own! I work a 9 to 5, so anytime before 9 AM, during lunchtime, and anytime after 5 PM, I am available. Weekends I typically am available all day long! I’ll treat your dog like they’re my own! I’ll always follow any instructions you have for walks, feeding, routines, or anything else they need. I’ll make sure they’re safe, comfortable, and well cared for while they’re with me. I also know how important it is to trust someone with your pet, so I’ll keep you updated and make sure they get plenty of attention and care!
“Kelly came over for an initial meet and greet and quick walk. She was on time, friendly, and easy to communicate with, and we’d be happy to have her care for Lewis in the future.”
About: Hi! My name is Sophi and I have been taking care of dogs, cats, and a variety of other pets for over 6 years. Many families have relied on me to walk, feed, bathe, play with, and take care of their pets. I especially love playing with dogs and running around with them at a park! I am reliable, engaging, flexible, organized, and experienced, and will take care of your pets as if they were my own! I am a student and have classes during the week except on Fridays but my schedule is very flexible. My weekends are generally free as well. I love to take care of pets throughout the day or at night at any time. I care for my pets in my home with love, respect, and kindness. I make sure my pet is well fed, walked, bathed, and most importantly loved!
“Fiona has a great rapport with my dog and she’s so good at being flexible working around my schedule! She’s professional and timely communicating. She’s made a huge difference in my dogs quality of life and I’m so grateful for her!”
The median cost per walk for dog walking in Chestnut Hill is $25
Dog parents share their Rover experiences - Chestnut Hill
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?
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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 walking
1. Search
Browse profiles of walkers near you who offer dog walking.
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 walking - Chestnut Hill
Select a filter and find qualifying sitters offering dog walking.Sitters in Chestnut Hill average 4 repeat dog walking clients
FAQs for Dog Walking - Chestnut Hill
Frequently asked questions about Rover
The average cost of Dog Walking in Chestnut Hill is $22 per walk as of November 2026. Most bookings cost between $15 and $28 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 10,811 sitters on Rover offering Dog Walking across Chestnut Hill. 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 Chestnut Hill. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Chestnut Hill after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the 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 Chestnut Hill. On Rover:
- 85% of walkers can help with special care needs
- 89% can help with giving oral medications or injections
- 95% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
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