Dog Sitting Chestnut Hill
Book a Chestnut Hill dog sitter to watch your dog in your sitter’s home or yours.

Over 34 pet parents in Chestnut Hill have booked dog sitting
Chestnut Hill, Find top rated dog sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: Hi there! I'm a reliable, compassionate dog lover who understands that every dog deserves patience, kindness, and individualized care. I know that trusting someone with your pet is a big decision, and I don't take that responsibility lightly. My goal is to make both you and your dog feel comfortable, safe, and confident every step of the way. I believe dogs are family, and I care for every dog as if they were my own. Whether your pup is energetic and loves long walks, prefers a slower pace, or simply enjoys companionship, I'm happy to adapt to their unique personality, routine, and needs. I pay close attention to details, including feeding schedules, medications, preferred walking routes, potty breaks, and any special instructions you provide. I'm attentive during every walk and visit, always keeping your dog's safety as my top priority. I'll make sure they have plenty of exercise, affection, fresh water, and positive attention while they're with me. I understand that consistency is important, so I do my best to maintain the routine your dog is already familiar with. Communication is also very important to me. I'll keep you updated with photos, messages, and details about how your dog's visit or walk went, so you can have peace of mind while you're away. I want you to know that your pet is happy, safe, and well cared for. Whether your dog loves to play, explore, cuddle, or simply enjoys a calm, reassuring presence, I'm committed to providing a positive experience filled with patience, love, and respect. My goal isn't just to walk dogs—it's to build lasting relationships with both pets and their owners based on trust, reliability, and genuine care. I cared for my miniature Sheltie from his energetic puppy years through his senior years, including helping him navigate severe rheumatoid arthritis with patience, love, and compassion. That experience taught me how important it is to be attentive to each dog's unique needs. I strive to provide every pet with thoughtful, reliable care, treating them like family because that's exactly what they deserve. I would be honored to care for your furry family member, and I look forward to meeting you and your best friend! I recently transitioned from my full-time role as a paralegal at a law firm in downtown Boston and am dedicating my time throughout July and August to caring for pets. This allows me to offer a flexible schedule and give each dog the time, attention, and care they deserve. Whether your pet needs a walk, companionship, or extra attention while you're away, I'm happy to work with your schedule whenever possible. My goal is to provide reliable, attentive care that gives you peace of mind and keeps your dog happy, comfortable, and well cared for. I have a fully fenced yard and live near several parks in Brighton's Oak Square neighborhood, providing plenty of opportunities for safe outdoor exercise and enrichment. I don't currently have a dog of my own, as my beloved Sheltie passed away two years ago, which means any dog in my care will receive my full attention. Whether I'm caring for a pet in my home or in a client's home, I prioritize keeping them comfortable by following their normal routine as closely as possible. I carefully follow feeding schedules, walking routines, medication instructions, and any special care requests. I believe consistency helps dogs feel secure, so I take the time to learn each pet's personality, preferences, and needs. My goal is to provide a safe, loving, and low-stress environment where your dog feels cared for, happy, and at home while you're away.
“Eveline offered drop-in visits throughout a week for my cat while I was away. She was super reliable and punctual with her visits and provided immediate communications. My main ask was for her to clean the litter box, but she also offered to hangout with my cat and gave him brushing sessions! Eveline was also super accommodating and reliable for picking up and dropping off my keys.”


About: I grew up surrounded by pets. Both my neighbor and my grandma had cats that loved to explore the outdoors, so I spent many summer days playing and exploring with them. During quarantine, my cousin got an Australian Cobberdog named Rosie. When they were away, I would frequently volunteer to be the one in charge of caring for her. In recent years, when my friends were away they would trust me to walk and take care of their pets. Over the years I have gained a lot of experience caring for cats and dogs of all shapes and sizes, and am so excited to meet your pet! During the months of May-August I am situated in Newton MA. During the months of September-April, I split my time between Amherst MA where I go to school at UMass and Newton. I think pet care is a two way street. I can only provide my best care if I know your pets needs. I preform my best when I know everything I need to know about your pet.
About: I’ve watched after friends/neighbors pets (dogs, cats, fish). While I don’t have any pets in my current home, I was raised with both dogs and cats! I am currently on summer vacation, so I will have free time throughout the day or evening to care for your pet(s)! I am very flexible with timing, so I can work around your schedule. My focus will be on building trust with your pet and helping them feel safe while you are away. I am very patient and will focus on what the pet needs in the moment to help them feel more comfortable.
“Anna did a great job at caring for my cat. She followed all the instructions I gave her, gave me daily updates, and my cat warmed up to her super quickly. I would definitely book with her again the next time I have to go away!”

“Lani did a great job taking care of my cat and my (very old) Chinchilla!! She was totally reliable, showed my pets lots of love and attention and communicated well with me regularly. I will definitely hire her again!”

“Alyssa was amazing for my dog and me. Highly recommend. I had a last minute business trip and she was able to drop in to save the evening and walk Louie while I was out of town. And it was her first walk with us. She knew just what to ask during the meet and greet and then again right before the walk to make it be a success for her, me and most importantly Louie! Thx!!!!”

About: I have taken care of pets my entire life! I am lucky to have cared for pets across their entire lives, from puppy/kitten to lovely senior pets. I am currently volunteering at a cat shelter in Boston and would love to bring that experience to your pets. I love pets of all shapes and sizes, but I absolutely adore caring for big dogs and shy cats. I volunteer at a cat shelter in Boston three days a week, but I am otherwise free all throughout weekdays to look after your pets! I am happy to do morning or midday visits to take special care of your pets. I think it is incredibly important that caring for pets does not disrupt their regular habits or schedule! It's so important to gain the trust of people's pets in order to properly care for them, and so I will do everything I can to make sure that your pets feel safe and comfortable while I make sure their needs are met.
“Sydney was wonderful to work with. The cats took to her easily, she communicated well and accomplished everything we needed from her. Because of her care we were able to fully enjoy our trip. Thanks again!”

About: I’ve been a lifelong dog lover and had the joy of raising my own Boxer for 13 wonderful years. In addition to caring for my own dog, I’ve provided pet sitting for many friends’ and family members’ dogs, both in their homes and in mine. I’m an active person who loves getting outside, and I enjoy having a four-legged companion join me on long walks and adventures. I also have a spacious SUV, making it easy and comfortable to safely transport dogs of all sizes if needed. I understand that every dog has their own personality and routine, and I’m committed to providing loving, reliable care so you can feel confident your pet is in good hands. I work from home mostly and available mornings, lunch and afternoons. Also available on weekends to pet sit at my place or at the pets home. I live in a condo near a park and reservoir with nice path for walking dogs. Happy to stay at pets home as it might be most comfortable for them and their routine.
“Nimisha was wonderful. My two dogs got walks and cuddles and they loved all the attention they got on their visits. There were many picture updates during visits as well. Will absolutely book with Nimisha again!”

“It was the first time we called on Stuart to walk Clare, not just once, but twice in a day, and we’re glad we did. Stuart was conscientious from the start, offering to stop by the day before we needed him to meet us and Clare. We highly recommend him!”

About: My name is Mari and I am a recent graduate from Johns Hopkins University and working in Longwood! I am a big pet lover and love taking care of pets, since I am not in the stage of my life where I can have one of my own right now. I have a golden doodle of my own at home in Virginia and she is the best part of my life! I cherish spending time with her and get nervous when my family has to leave her, so I understand some of the worries pet parents may have! I have been responsible for pet sitting dogs throughout high school and have extensive experience with walking, feeding, and cleaning up after dogs. I also have been walking dogs in the Boston area for a few months now. I am looking for new client in the Washington Square area! I work a hybrid schedule and normally go in about once a week for a few hours! I am able to drop by at any time needed because of this flexibility. I am willing to follow any instructions provided on caring for your dog in your home! I have experience with letting dogs out and walking them during visits.
“Sarah is amazing! We've booked her twice and both times have come home to a happy and healthy kitty. Our cat absolutely loves her, and we feel so secure knowing she is taking care of him while we are away.”

The median cost per visit for dog sitting in Chestnut Hill is $25
Dog parents share their Rover experiences - Chestnut Hill
Sydney is amazing!!! She has lots of experience working with dogs and it shows. Mine can be a bit rowdy at times but she had them sitting and calm within like a minute of being there! She’s super sweet and communicative as well. We would 100% use Sydney again. I had 0 concerns after meeting her and our experience was great!

It’s hard to tell who has more fun when Megan walks Clare! Today, they explored far beyond what I booked Megan to do. We ‘ve been relying on Megan for two walks each time we call on her, and she’s very responsible, considerate, and loving to Clare, always adding tummy rubs and topping off her food and water before she leaves.

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 dog sitting
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 sitting - Chestnut Hill
Select a filter and find qualifying sitters offering dog sitting.Sitters in Chestnut Hill average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Chestnut Hill
Frequently asked questions about Rover
The average cost for Dog Sitting in Chestnut Hill on Rover is $19.26 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting 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 Dog Sitting. For more information on service fees, click here .
As of August 2026, there are 10,583 sitters on Rover offering Dog Sitting across Chestnut Hill. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chestnut Hill stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Chestnut Hill choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Chestnut Hill with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Chestnut Hill. On Rover:
- 91% of sitters can help with special care needs
- 96% 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.
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.






















