Dog Sitting Chestnut Hill
Book a Chestnut Hill dog sitter to watch your dog in your sitter’s home or yours.
Over 45 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%.
“Allison was absolutely wonderful with my two cats, Ozzy and Willis. She was prompt, documented excellent pictures and a summary of her visit, following exact instructions for care. I would absolutely hire her again and recommend her for your pet’s needs.”
About: I have grown up with dogs my whole life and love them! I am very familiar with the mental and physical stimulation needed for high-energy dogs. In addition, I have had 2 years of experience with caretaking for senior and special needs dogs. I am available for dog walking and drop-in visits as my class schedule and transport time allows—this is mostly weekday afternoons, some evenings, and weekends! I provide attentive, customized pet care in clients’ homes, including feeding, walking, playtime, administering medications, crating, cleaning, and following any special instructions to ensure comfort.
About: I’ve taken care of dogs since I was a young girl. Growing up, I’ve owned and been trusted to watch a wide range of pets, but I love being around dogs of all ages! I’m currently a graduate student, with classes only taking up half of my week, so I have multiple days I can devote to pet care! Usually, Thursdays/Fridays/Saturdays are my pet days. When entering your home, respect is my top priority. It’s a privilege to be let into your space, and I will respect your home and pet as if they were my own.
“Sarah was excellent! She was very prompt and thorough in all of her communication leading up to and during the drop-in visit. She took great care of our dog. I highly recommend Sarah!”
“Maegan was incredible with Jax, helping with his special needs and ensuring he was comfortable and loved whole I was away. Maegan provided excellent communication, providing detailed write ups and taking lots of pictures for each visit. I would highly recommend Maegan to anyone looking for a caring and thoughtful sitter! Thank you!”
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.
“Jana was great with my two dogs! Sent lots of photos and info on how the visit went and she above all made sure that both dogs had a safe visit. I will definitely be using her again.”
About: I've been accustomed around pets my whole life. Currently I am an owner of two cats and two dogs, so I have good experience with both animals who are each very different in their own right. Very flexible and eager to see your pet! :) Currently I am a incoming MCPHS student studying to get my Doctorate in Pharmacy. I am mostly open later into the afternoons typically after the times of 2-3p.m. Every Tuesday I am not free as I have D&D. Raising my pet I always taught them to be smart, as in when my cat was a kitten I would always press on his paws, and now he can open up doors and containers. For my dog i've thought him to come to me and be able to signal for his wants and needs; however for pets that were not of my own I was vigilant with them. Checking and making sure they were constantly with me whenever I would shift my attention and focus elsewhere. I always follow the schedules that owners have for their own pets; as throwing that out of sync wouldn't just throw the pet, but also their owners schedule too. We all have scheduled times with our pets whether we realize it or not, my job will be to keep that norm when you might not be able to.
About: I grew up with animals. Dogs and cats specifically have always been apart of my life. I am able to keep up with with the youngest peppy puppy or slow down to meet the pace of a senior dog. I am not fazed by much and happy to provide the same love and care that you would give to your animal. I am a freelancer with a very flexible schedule. I have the ability to work with you on potential last minute needs and care for your pets. I am very comfortable caring for animals weather it be a quick check at the home ot in an more outdoor adventure. My goal is to give your animal the care they care they need in the environment that works best for you and them.
“As always, Pricilla did a great job! She made several visits to check on my cat while I was out of town. He is a needy cat and really needs attention and he was very happy when I came back!”
The median cost per visit for dog sitting in Chestnut Hill is $25
Dog parents share their Rover experiences - Chestnut Hill
Emily was absolutely wonderful! She was able to help me out with a last minute request, and I really appreciated that she took the time to meet with me beforehand so we could make sure everything was a good fit before officially booking. She kept me updated throughout the visit and sent plenty of pictures and videos, which gave me so much peace of mind. I’m so thankful I found Emily, and would definitely recommend her to anyone looking for a reliable and caring sitter!
Lorena & Jahn are wonderful with our pup Caddie! Caddie is a young, energetic puppy, and they were extremely helpful in keeping her happy and engaged during her 30-minute drop-in visits. They communicate very well, giving us updates at each drop-in visit with photos. We will definitely book with Lorena & Jahn again! Highly recommended
Tess looked after my puppy for me while I was at work this summer and I couldn’t think of a better person for the job! She was so communicative and detail oriented, took great notes on his eating and bathroom schedule. My roommates continuously commented on how sweet she was with him and how well he did with her! I couldn’t recommend her more!!
Amanda was punctual, communicative, and clear about what my dog Charlie was doing. Most important, she was sweet and kind to Charlie, giving her belly rubs and love. I appreciated her kind demeanor and how responsible she was in leaving everything the way I requested. I would request Amanda with enthusiasm next time I need someone to come walk and watch Charlie!
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 Dog Sitting - 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 September 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 September 2026, there are 10,481 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:
- 90% of sitters can help with special care needs
- 95% 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.
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