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

Over 41 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%.
“Jana was a perfect dog sitter! She accepted the job on very short notice and arrived early. She really saved the day! She was very gentle and loving with my tiny chihuahua puppy. I loved getting the picture updates. Thank you, Jana!”

About: I’ve been caring for dogs since I was 14, starting by watching my neighbors’ pets when they went on vacation. Since then, I’ve had the chance to care for many other dogs in my neighborhood, as well as the dogs of my professors at UMass. I also have experience using clicker training. I’ve always dreamed of having dogs of my own, but frequent moves over the years have made that tough. From going to college and then moving to Boston. Getting to spend time caring for your dogs would truly mean a lot to me and would let me enjoy some quality time with furry friends while making sure they’re happy, safe, and well cared for. I work remotely and have a very flexible schedule, so I can make myself available most times during any day of the week. I don’t have any vacations planned and am available for the foreseeable future. I’m attentive, responsible, and committed to following your care instructions closely so your pets feel safe and comfortable at home. I always make sure all expectations are met and that your pets receive the care they deserve.
“Sydney was so great! She fit us in to a busy holiday weekend last minute and was very communicative about our two cats--she even cleaned up some vomit (yuck!) and tracked our nervous cats to their hiding places to get pictures for us. Would def recommend!”

“Julia took great care of our cat! She is communicative, reliable, understood/followed all care instructions, and clearly an animal lover. We knew our cat was in good hands. Highly recommend Julia for your animal sitting!”


About: Hi! I’m Allison, and I’m a rising junior at Cornell University studying Animal Science on the Pre-Veterinary track. My experience includes volunteering at a therapeutic riding center, working with farm animals, and spending time at a Fear Free certified veterinary practice. Through those experiences, I’ve learned how to read animal body language and help pets feel more comfortable in unfamiliar situations. I have a dog of my own, Percy, so I understand how much trust goes into leaving your pet with someone else. I enjoy getting to know each pet and figuring out what helps them feel comfortable. I’ll follow your pet’s routine closely and make sure you receive updates while you’re away! I’m home from university for the summer, which gives me a pretty flexible schedule! I’m available most days and can work around your pet’s routine, whether that means walks or drop in visits. I’ll be in the area through mid-August and can usually accommodate weekday and weekend requests. I’m comfortable caring for dogs with different temperaments and energy levels. Through my experience in animal care and at a Fear Free certified veterinary practice, I’ve learned how to read body language and recognize when a pet may be feeling stressed or uncomfortable. I always follow instructions closely and take the time to make sure each pet feels comfortable in my care. I’m also happy to provide updates and photos so you know how your pet is doing while you’re away.
About: What sets me apart is my lifelong experience with dogs and the genuine love and care I bring to every pet I watch. I have been dog sitting for years and currently have two dogs of my own, so I understand the responsibility and attention that goes into caring for pets. As a dog owner myself, I know how important it is to find someone trustworthy and reliable. I treat every dog as if they were my own, making sure they feel safe, comfortable, and loved while their family is away. I am attentive to each dog's individual needs, whether that means lots of playtime and exercise, sticking to a specific routine, or providing extra patience and affection. I pride myself on being dependable, communicative, and caring, and I always strive to give both pets and their owners peace of mind. Pet care fits naturally into my daily routine because I have two dogs of my own who I care for every day. I also work a remote internship, which gives me a flexible schedule and allows me to be home throughout the day. This means I can provide plenty of attention, walks, playtime, potty breaks, and companionship for the pets I care for. Because I'm already used to building my day around caring for dogs, pet sitting is something I truly enjoy and can easily incorporate into my routine. I understand how important consistency is for pets, and I make it a priority to ensure they feel comfortable, safe, and loved while their owners are away. Whether I am caring for pets in my own home or in a client's home, I always focus on keeping their routine as consistent as possible. I make sure pets are fed on schedule, have fresh water, get plenty of exercise, bathroom breaks, playtime, and lots of attention and affection. I understand that every pet is different, so I take the time to learn their specific needs, preferences, and routines. If I am caring for a pet in a client's home, I respect their space and follow all instructions carefully to help their pet feel comfortable in a familiar environment. As a pet owner myself, I know how important communication is, so I am happy to provide updates and photos to give owners peace of mind while they are away. My goal is always to make pets feel safe, happy, and loved, just like they would with their own family.

About: I’ve taken care of pets since I was 13. I grew up with a King Charles cavalier who I love dearly . My friends , neighbors, and family have trusted me with their pets 🫶🏼 from dog walking, house check-ins, and over night stays I am currently looking for new work so I’ll have tons of time to give your fur babies during the day! There will be tons of time for walks and belly rubs Pets are always around me when I care for them to make sure they’re safe. My apartment is clean and tidy. They receive tons of play time, walks, and cuddles :)
“Olivia took great care of our dog during drop-in visits for two weeks while our schedules were hectic. She provided lots of updates and was proactive and easy to communicate with. Would highly recommend her services and look forward to working with her again!”

“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!”

“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.”

About: I've have grown up surrounded by animals (2 dogs, 2 cats, and 2 brothers!). I have experience in short and long term dog & cat sitting. My most interesting sitting experience was watching 5 cats at once (the more the merrier)! I also have experience taking care of small animals including hamsters and guinea pigs. With my family, I have helped to foster and find the forever homes for 2 dogs, 1 adult cat, and 2 kittens! I have experience and am comfortable working with shy and nervous animals. I am a student at Boston College living in Newton for the summer. I am currently taking classes and am a research intern which take up roughly 2-4 hours a day. I also work in downtown Boston on Monday's and Wednesday's between 9am-5pm. While I do not have a car, I am well versed in Boston public transportation. I am a very active person and would be happy to take your pups walking, running, and on hiking adventures! For services in my home: I currently live with 1 roommate and do not have any pets. I am comfortable with short-term boarding (no longer than 4 weeks) for dogs and cats. I have an unfenced backyard but have close access to a fenced in dog-park. My apartment is on the second floor - a concern for older dogs who might have trouble with stairs. For services in client homes: I am able to stay in client homes & I am clean and quiet! I am happy to complete cleaning services or other house-sitting tasks along with caring for your dogs, cats, or small animals. I am also comfortable visiting client homes periodically, including multiple times a day if needed.
“Jose was awesome with our 3 cats while we were away for a long weekend! Great communication and super responsible. We would definitely have Jose watch our cats again.”

“Shilpa was wonderful! She took great care of my cat over a long week and was communicative and flexible with dealing with any requests we had! In the future I would absolutely love to have her care for my cat again!”

“Julia was great with my cat Toto! She was always on time and sent photos for each visit. She’s very responsive, reliable and sweet. I look forward to booking her again!”

“Lauren was great with Deva! This was my first time leaving Deva and Lauren sent so many great pics and updates and really seemed to understand Deva’s personality! Will definitely ask Lauren to care for Deva again!”

The median cost per visit for dog sitting in Chestnut Hill is $25
Dog parents share their Rover experiences - Chestnut Hill
Jamie was absolutely wonderful! This was my first time booking with her, and I left what felt like a million notes and instructions. Jamie took the time to read every single one and followed them so thoughtfully and carefully. It was clear from the start that she genuinely cared about providing the best possible experience for both me and my pet. She was kind, attentive, communicative, and incredibly detail-oriented throughout the entire stay. Knowing that someone took the time to understand all of my routines and preferences gave me so much peace of mind. I am so grateful for the excellent care Jamie provided and would absolutely book with her again without hesitation. Highly recommend!

Olivia took great care of our dog during drop-in visits for two weeks while our schedules were hectic. She provided lots of updates and was proactive and easy to communicate with. Would highly recommend her services and look forward to working with her again!

Alyssa took amazing care of my dog and cat while I was away for a work trip. She was very kind and understanding about my nerves of being away and leaving them but she was able to ease my worries with all of her detailed updates and many pictures of my pets. Thank you so much Alyssa!

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 Rover works

1. Search
Browse profiles of sitters near you who offer dog sitting
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 Chestnut Hill sitters!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 July 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 July 2026, there are 10,599 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
- 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.





















