Dog Sitting Chestnut Hill

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

End Date
Search

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%.

1 / 1
Sitter Profile Image: Wendy L.
Verified Enhanced Background Check
Wendy L.
$19
total per visit
5.0 out of 5 stars
8 reviews
4 repeat clients
10 years of experience
Boston, MA, 02135

Was able to get Wendy at short notice. She was on time, Communicated promptly with me and made sire Mia had a good time with her. Thanks Wendy

Profile image
Rob N.
Sitter Profile Image: Gabriel B.
Verified Enhanced Background Check
Gabriel B.
Star Sitter
$28
total per visit
4.9 out of 5 stars
78 reviews
17 repeat clients
10 years of experience
Boston, MA, 02130

Gabriel is great. He is dedicated to making sure animals are comfortable with him and provides amazing care. His communication is also great.

Profile image
Christopher M.
Sitter Profile Image: Jana W.
Verified Enhanced Background Check
Jana W.
Star Sitter
$29
total per visit
5.0 out of 5 stars
294 reviews
89 repeat clients
30 years of experience
West Roxbury, West Roxbury, MA, 02132

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!

Profile image
Barbara B.
Sitter Profile Image: Nhu Thieu L.
Verified Enhanced Background Check
Nhu Thieu L.
Star Sitter
$34
total per visit
5.0 out of 5 stars
16 reviews
5 repeat clients
10 years of experience
Allston-Brighton, Boston, MA, 02135

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.

Sitter Profile Image: Grace S.
Verified Enhanced Background Check
Grace S.
$25
total per visit
5.0 out of 5 stars
22 reviews
9 repeat clients
15 years of experience
Brookline, MA, 02445

Grace was very receptive to our requests and was a good companion for our puppy during a 1 hour drop in visit. She is also flexible about scheduling. We will be booking again.

Profile image
Fiona L.
Sitter Profile Image: Sydney P.
Verified Enhanced Background Check
Sydney P.
$28
total per visit
4.9 out of 5 stars
64 reviews
23 repeat clients
5 years of experience
Allston-Brighton, Brighton, MA, 02135

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!

Profile image
Erica S.
Sitter Profile Image: Julia W.
Verified Enhanced Background Check
Julia W.
Star Sitter
$33
total per visit
5.0 out of 5 stars
24 reviews
5 repeat clients
10 years of experience
Watertown, MA, 02472

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!

Profile image
Katie V.
Sitter Profile Image: Allison F.
Verified Enhanced Background Check
Allison F.
$28
total per visit
10 years of experience
Newton, MA, 02467

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.

Sitter Profile Image: Augusta G.
Verified Enhanced Background Check
Augusta G.
$23
total per visit
8 years of experience
Allston-Brighton, Boston, MA, 02135

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.

Sitter Profile Image: Chloe H.
Verified Enhanced Background Check
Chloe H.
$28
total per visit
13 years of experience
Allston-Brighton, Brighton, MA, 02135

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 :)

Sitter Profile Image: olivia a.
Verified Enhanced Background Check
olivia a.
$28
total per visit
5.0 out of 5 stars
17 reviews
2 repeat clients
10 years of experience
Brookline, MA, 02446

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!

Profile image
Lawrence M.
Sitter Profile Image: Anna H.
Verified Enhanced Background Check
Anna H.
$28
total per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
24 years of experience
Allston-Brighton, Boston, MA, 02135

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!

Profile image
Julia B.
Sitter Profile Image: Sarah B.
Verified Enhanced Background Check
Sarah B.
$39
total per visit
5.0 out of 5 stars
28 reviews
8 repeat clients
15 years of experience
Boston, MA, 02135

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.

Profile image
Emily R.
Sitter Profile Image: Abigail F.
Verified Enhanced Background Check
Abigail F.
$20
total per visit
5.0 out of 5 stars
2 reviews
1 repeat client
5 years of experience
Newton, MA, 02467

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.

Sitter Profile Image: Colleen N.
Verified Background Check
Colleen N.
$23
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Newton, MA, 02461

I highly recommend Colleen and plan on calling her again.

Profile image
Lisa T.
Sitter Profile Image: Jose Q.
Verified Enhanced Background Check
Jose Q.
Star Sitter
$23
total per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
12 years of experience
Allston-Brighton, Brighton, MA, 02135

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.

Profile image
Rachael F.
Sitter Profile Image: Shilpa J.
Verified Background Check
Shilpa J.
Star Sitter
$28
total per visit
5.0 out of 5 stars
69 reviews
30 repeat clients
Allston-Brighton, Brighton, MA, 02135

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!

Profile image
Katie T.
Sitter Profile Image: Julia J.
Verified Enhanced Background Check
Julia J.
Star Sitter
$32
total per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
15 years of experience
Boston, MA, 02135

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!

Profile image
Alina Q.
Sitter Profile Image: Lauren V.
Verified Enhanced Background Check
Lauren V.
$34
total per visit
5.0 out of 5 stars
64 reviews
19 repeat clients
13 years of experience
Allston-Brighton, Brighton, MA, 02135

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!

Profile image
Jennifer & Rick B.
Sitter Profile Image: Megan J.
Verified Enhanced Background Check
Megan J.
$23
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
8 years of experience
Brighton, MA, 02135

Megan was great!

Profile image
Allison B.
1 / 1
View more sitters

The median cost per visit for dog sitting in Chestnut Hill is $25

Dog parents share their Rover experiences - Chestnut Hill

1 / 1
5.0 out of 5 stars

We’re grateful to Stuart for taking Clare out on two walks today, and being responsible on a 100°day, and cutting one of the walks short, and instead hanging out with Clare indoors for the duration of the visit.

Profile image
Ted C.
Drop-In Visits
5.0 out of 5 stars

Traci was an excellent dog-walker for us! She kept us updated and provided pictures throughout the weekend as well as little updates. We will definitely book with her again!

Profile image
Kyle W.
Drop-In Visits
5.0 out of 5 stars

Lianne is great!! I needed a dog sitter very last minute and she was so kind to help out. She took great care of Ellie, was timely, and sent detailed cards about her visits. I will definitely be reaching out again and would recommend!!

Profile image
Rylee S.
Drop-In Visits
5.0 out of 5 stars

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!

Profile image
Ms. J.
Drop-In Visits
5.0 out of 5 stars

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!

Profile image
Lawrence M.
Drop-In Visits
5.0 out of 5 stars

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!

Profile image
Viviana G.
Drop-In Visits
5.0 out of 5 stars

Buddy loved meeting Michele! She was great meeting us before hand and catering to my old guys needs! He had a great visit!

Profile image
Stephanie R.
Drop-In Visits
5.0 out of 5 stars

Thank you Kristen! I hope it wasn’t too hot for you and your little. He may have wanted to stop across from Dane Park. Because he usually goes in there. Thanks again :)

Profile image
Deborah D.
Drop-In Visits
5.0 out of 5 stars

Fabulous!!! Tosh and I have had the best experience with Mel. He loves her and I can’t say enough good things.

Profile image
Priscilla M.
Drop-In Visits
5.0 out of 5 stars

Grace took excellent care of our boy Rua with weekly visits over a few months. We will definitely book again when we need her.

Profile image
Fiona L.
Drop-In Visits
5.0 out of 5 stars

Zilalai is so amazing! She is reliable, flexibility, professional, and goes above and beyond making sure you are well informed. We are so grateful for her!

Profile image
Alexis K.
Drop-In Visits
5.0 out of 5 stars

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.

Profile image
Cecilia Y.
Drop-In Visits
5.0 out of 5 stars

Sam was very nice and punctual. He communicated any questions he had right away. My dog definitely liked him!

Profile image
Sarah M.
Drop-In Visits
5.0 out of 5 stars

Chelseigh was excellent with Petey who is reactive. She was patient, consistent, reliable, and caring.

Profile image
Molly M.
Drop-In Visits
5.0 out of 5 stars

It was REALLY HOT that day! Sorry you two had to meet on such a bad weather day. You were very sweet to try to bring her back home— she looked very uncomfortable. I’ll bet you were too! Thanks so much

Profile image
Barbra & Doug S.
Drop-In Visits
5.0 out of 5 stars

Emma was very responsive, and so easy and friendly to work with for our very last minute drop in request. She did everything we asked and it was obvious through her pictures our dog was very comfortable with her. Thanks so much!!

Profile image
Emma
Drop-In Visits
5.0 out of 5 stars

Emma was a fantastic dog care person for our beloved Sammi! She went the extra mile to help, when a problem arose. We look forward to booking her again in the future! Thanks, Emma!

Profile image
Ann P.
Drop-In Visits
5.0 out of 5 stars

Emily is amazing! She is so sweet, genuinely loves and wants to spend time with dogs, and respects a schedule you’d like her to follow. Not only would I request her again in the future, but I also wouldn’t hesitate to recommend her to others.

Profile image
Abbey C.
Drop-In Visits
5.0 out of 5 stars

Thank you for taking care of Duke, always being communicative and proactive about letting us know how Duke was doing. We enjoyed all The little details about your time with him and the photos. We found him in amazing spirit when we got back.

Profile image
Ayan M.
Drop-In Visits
5.0 out of 5 stars

Jana was able to take care of our fur babies (one large dog, one cat) on pretty short notice and was so pleasant and communicative the entire time! She was wonderful to work with and we will keep her in mind for future pet care needs!

Profile image
Ashley W.
Drop-In Visits
1 / 1
Find pet care near you

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. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge