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.”
“Hannah is reliable and flexible with my animal’ needs. I’m so happy that she could work with me, and I will definitely check with her again when I need someone to check on my pets.”
About: I am an absolute dog-lover and will provide your pup with the care and affection they need. I am open to pet sitting, dog walking, or quick pop-ins. If your dog loves walks and exploring the outdoors; if you need a reliable dog sitter; and if you want to have confidence in your dog's safety while you're away, please contact me and I would be thrilled to discuss what works best for you and your pup. I work from home and am available for walks most days of the week, with flexible timing. I can dog sit week days and weekends with proper notice. I prefer to stay in my clients homes where the dog is most comfortable, offering a gentle transition to your absence! I do offer stays at my home, however the dog must be house trained but I have great walking areas around me and a small backyard.
“Anastasia was fantastic! She went out of her way to make sure our little scaredy cat Jake was super comfortable, and even went back to double-check on his comfort. She also was very communicative and prompt. And even brought in our mail! We will definitely be asking her for her services again! She’s wonderful!”
“Stitches’ tail doesn’t wiggle for just anybody—but with Julia, it never stops! He can instantly sense her great energy, and it’s clear how comfortable and happy he feels around her. She’s so patient, caring, and attentive with him, and even in just 30 minutes, she makes such a positive difference in his day. It gives me so much peace of mind knowing he’s in such good hands. Julia is truly amazing with him, and I couldn’t ask for a better dog walker and sitter! 🐾”
“Allie was wonderful taking care of my cat! She came over to meet him before taking care of him and was so warm and friendly. She was communicative and consistently gave great updates. Allie fed the cat, gave him insulin, and took care of his litter boxes and water. She also spent lots of time with him, which I really appreciated! Allie was great and I definitely recommend her!”
“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!”
“Jana helped us out very last minute! She was flexible when I asked her to come a little earlier. Will definitely request Jana again. Highly recommend!!”
About: I’ve had pets for my entire life, so I have experience with young and old dogs alike. My favorite thing to do is hangout with my dog, and I’d love to become friends with yours too! I love to walk, even more so if I have a companion with me! I’m currently working part time, so I have plenty of time to care for your pets, especially during weekdays! My schedule is flexible and I can work around your needs. I head back to college in September, so my location will change then, but I am more than happy to help you out this summer! I will always prioritize your pet’s safety and comfort during visits, making sure to follow your instructions carefully. I will make sure to provide updates and maintain consistent communication! I keep the environment calm, clean, and structured.
“Cynthia is incredible. She was attentive to my shy cat & went above/beyond to check in with me and communicate about her care. Will DEFINITELY use her again and highly recommend her to others.”
“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 taken care of neighbors & family friends dogs since middle school, doing drop-ins, walks & overnight stays. I also have experience with senior dogs, both my own & friends’ who I’ve cared for. My childhood dog, and best friend, passed away almost two years ago, and as a huge dog lover, I’ve been missing having a pup in my life! I would love to love yours <3 I work a full-time job, but am hybrid, so I’m only in the office Tuesdays & Wednesdays! I can do walks in the mornings before work on Monday or Friday, after work any day of the week (adjusting for the commute on Tuesday/Wednesday), and can be free on the weekends! If you’re near where I live, I could also pop in during the work day on my remote days. Unfortunately our apartment doesn’t allow dogs :( But I will follow your lead on what works best for you & your pup(s) in your space! I want to make sure everyone feels comfortable with the routine & arrangement!
“Claudia is an amazing pet sitter. She's incredibly considerate of our skittish kitty. Giving her plenty of time and space to get comfortable. Thanks to her, Smokie, our adult cat, is in wonderful hands when we're away. Can't recommend her enough!”
“Kevin is awesome! Went above and beyond to take care of my two cats. Helped me figure out what was wrong with my auto cleaning litter box. Couldn’t recommend him enough! Thanks again Kevin.”
“Sarah was so great!! She really came through for a slightly last minute booking. She provided timely updates and plenty of cute pictures of our Freya 💕 It seems like our baby had such a good time ☺️ Would definitely rebook and recommend Sarah for her services!”
“Leanne is such a wonderful sitter for my cat Ellie! She looks after her with so much care and love. I used to feel much more anxious leaving Ellie but now I always know she is in good hands with Leanne.”
About: Hi! I'm a recent graduate who lives with a senior cat; I have a lot of experience with senior pets, special needs pets, medication administration, etc. I'm able to exercise with and play however your dog likes! I've been pet sitting and walking dogs for my friends and family (and Wag!) for over a decade (dog in the profile picture is my brother's dog Kuma!) Pets bring me so much joy and I want to help take care of them as a community effort :) I'm here to build trust, please ask any questions 🫰 I am a gig worker currently, therefore very flexible—request me and there's a high chance I'll be available! I'm around weekends and weekdays, my own cat has plenty of alternate caregivers. I would not be able to host pets in my home, but would follow any rules at clients homes to make pets feel safe and regulated :) consistency helps them and me!
“Amarais was very attentive to my cat & took the time for an intro visit before my trip. I really appreciate that she took time to brush him out & water my outdoor plants.”
“Nick was great with our cat Delilah! He was very professional and came and met her ahead of time. She was very comfortable with him as we saw through many cute photos! We would definitely book with Nick again.”
The median cost per visit for dog sitting in Chestnut Hill is $25
Dog parents share their Rover experiences - Chestnut Hill
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 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 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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