Dog Sitting in Chestnut Hill

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

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Top rated Chestnut Hill dog sitters

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Kim W.
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Kim W.
Star Sitter
$28
total per visit
5.0 out of 5 stars
18 reviews
6 repeat clients
5 years of experience
Newton, MA, 02459

About: I am a lifelong dog lover and animal person. I grew up riding horses and spent years at the barn caring for the horses, dogs, and cats. I've had my own dogs and taken care of other people's. I would love to take your dog for walks and spoil them with love! I am also licensed in my town and have pet sitting insurance outside of Rover's insurance. I have a flexible job and work from home most days. I can fit in walks or be around the house with your dog. I have a secure and good sized fenced in yard and live near a dog park as well if your dog is okay with other dogs. I balance spoiling dogs with lots of love, treats, and pats with making sure dogs get whatever individual care they need including feedings, exercise, and medications if needed.

Sitter Profile Image: Jana W.
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Jana W.
Star Sitter
$29
total per visit
5.0 out of 5 stars
291 reviews
89 repeat clients
30 years of experience
West Roxbury, West Roxbury, MA, 02132

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.

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Korri C.
Sitter Profile Image: Wendy L.
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Wendy L.
$19
total per visit
5.0 out of 5 stars
7 reviews
3 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

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Rob N.
Sitter Profile Image: Grace S.
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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.

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Fiona L.
Sitter Profile Image: Stuart T.
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Stuart T.
$16
total per visit
5.0 out of 5 stars
6 reviews
1 year of experience
Allston-Brighton, Brighton, MA, 02135

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!

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Ted C.
Sitter Profile Image: Sydney P.
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Sydney P.
$28
total per visit
4.9 out of 5 stars
63 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!

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Erica S.
Sitter Profile Image: Shilpa J.
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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 took exceptional care of my senior cat, who requires daily medication, and handled everything with such care, patience, and reliability. She was clearly attentive to my cat’s needs, made sure her medication was given consistently, and kept me updated so I could relax while I was away. I would absolutely recommend Shilpa to anyone looking for a trustworthy and attentive sitter, especially for pets with special medical needs

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Molly J.
Sitter Profile Image: Adelle W.
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Adelle W.
Star Sitter
$29
total per visit
5.0 out of 5 stars
70 reviews
26 repeat clients
8 years of experience
Allston-Brighton, Brighton, MA, 02135

Adelle was amazing! So great with the cats, left great messages and took photos every day, and had no issues administering medicine to my temperamental cat! Would 100% book again

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Eden S.
Sitter Profile Image: Gabriel B.
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Gabriel B.
Star Sitter
$28
total per visit
4.9 out of 5 stars
77 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.

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Christopher M.
Sitter Profile Image: Sarah B.
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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.

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Emily R.
Sitter Profile Image: Lauren K.
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Lauren K.
$25
total per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
5 years of experience
Boston, MA, 02135

Lauren provided excellent in-home care and walks for our dog. Couldn’t be happier! 🐶

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Riana R.
Sitter Profile Image: Veronica P.
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Veronica P.
$23
total per visit
1 year of experience
Allston-Brighton, Boston, MA, 02135

About: I have been surrounded by animals all my life, starting with my cat Cheeks and leading to the 3 dogs and 2 cats that I have at home. Alongside taking care of my family animals, I have professional experience with Crossroads Campus, a dog adoption center and non-profit in Nashville, TN. I worked in dog care during Summer 2025, and I go back to work during my school breaks. My responsibilities included taking each dog on walks, spending personal time playing with them inside and outside, feeding them, monitoring their behavior in a kennel environment, and learning each dog’s individual personality. I felt connected to each dog and can proudly say that all the dogs I worked with have been adopted. Ultimately, dogs and cats remain an integral part of my life, and I want to continue to remain close to animals and take care of them while I spend my summer in Boston. I am currently interning at the International Institute of New England as a Legislative Advocacy Intern, and I am working on a hybrid schedule. I am unavailable on Thursdays when I need to go into the office, but otherwise, I'll be working remotely and will have lots of free time. I am located in Chestnut Hill, MA near Boston College, but I have access to both the T and a car, so it is easy for me to travel. Overall, I am very flexible with scheduling and will have tons of open time during the week to get outside with your pet when you need a date night or a couple days out of town. At home, I help my family by feeding our dogs morning and night and giving them the proper medication that they need. I also go outside with them and play in our backyard as well as take them to different dog parks near our house to let them get out of the house every so often. At Crossroads, I took each dog on a walk every day and helped with feeding and playtime. I love walking, running, and hiking, so getting your dog out for some exercise is a given for my work methods!

Sitter Profile Image: Julie J.
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Julie J.
Star Sitter
$23
total per visit
5.0 out of 5 stars
224 reviews
68 repeat clients
22 years of experience
Brookline, MA, 02445

I can’t say enough wonderful things about Julie! She treats our dogs like family, always reliable, caring, and communicative. The updates and pictures after each walk make me feel at ease knowing our dogs are happy and in safe hands. Our dogs absolutely adore her and it’s clear how much love and attention she gives. We feel so lucky to have found such a trustworthy and amazing walker on Rover!

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Riana R.
Sitter Profile Image: Maddie G.
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Maddie G.
$28
total per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Newton, MA, 02459

About: I have been working as a veterinary assistant for 4 years, and will be starting veterinary school in the fall. I am passionate about making pets feel safe, cared for, and happy in whatever ways I can. This is reflected in both my years working in the veterinary field, and the many years taking care of my own family dogs. While your pet is in my care, I treat them as my own! I am currently working per diem as a vet assistant, and enjoying the summer before I begin graduate school. I have very open availability on days where I am not working, which are reflected in my calendar. I have grown up around dogs and cats, and feel comfortable caring for and being around animals in all settings. I have lots of practice with walking dogs around other people, children, and dogs. My experience as a vet assistant allows me to be comfortable if your pet requires medication or specialized care during my time with them.

Sitter Profile Image: Lucy M.
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Lucy M.
$23
total per visit
10 years of experience
Allston-Brighton, Brighton, MA, 02135

About: I’ve had a dog in the family since I was 6 years old. Starting when I was 15, my family had at least 3 dogs. Right now they have 3 dogs and 2 cats. I am experienced in caring for animals compassionately. I have 3 years of experience in caring for dozens of ant colonies as well. I am currently working full-time, and my day ends at 3pm. I can feed your pet in the morning before 7am. My weekends are free as well! I live in a medium sized apartment with no yard, but there are two parks nearby for your pet to enjoy. I can provide them with food and water inside my home.

Sitter Profile Image: Sarah J.
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Sarah J.
$23
total per visit
5.0 out of 5 stars
39 reviews
12 repeat clients
4 years of experience
Boston, MA, 02135

Sarah was terrific with our pups while we were gone for the day. She took them for a walk then came back and gave them dinner. We got cute pics each time.

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Allison B.
Sitter Profile Image: Chelsea S.
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Chelsea S.
$28
total per visit
5.0 out of 5 stars
4 reviews
15 years of experience
Boston, MA, 02135

About: I grew up with cats, so I understand their needs. I have experience with all age levels - kittens to senior cats. Leaving your furry family members can be a stressful experience, but my goal is to make the experience as seamless as possible for both you and them! I also have a ton of experience walking and caring for dogs - from corgis to husky’s. During the week, I can visit pets in the evening after work. My weekends are flexible - so I can provide pet care whenever needed. Since I grew up with cats, I know what to look for in the home to ensure they're safe and happy while their family is away.

Sitter Profile Image: Linda G.
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Linda G.
Star Sitter
$28
total per visit
4.9 out of 5 stars
22 reviews
7 repeat clients
40 years of experience
Watertown, MA, 02472

Linda was terrific. She is reliable, detail oriented, and perceptive. She clearly cares deeply about animals. You can be sure your pet will be well cared for.

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Lisa G.
Sitter Profile Image: Colleen N.
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Colleen N.
$23
total per visit
5.0 out of 5 stars
4 reviews
10 years of experience
Newton, MA, 02461

I highly recommend Colleen and plan on calling her again.

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Lisa T.
Sitter Profile Image: Erin O.
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Erin O.
$19
total per visit
5.0 out of 5 stars
2 reviews
3 years of experience
Allston-Brighton, Boston, MA, 02135

About: I grew up with pet dogs, but fell in love with cats too after catsitting for a friend for several weeks! My own dog recently passed away (I adopted her as a senior but we had three wonderful years together) and I would love to continue to spend time with and take care of beloved pets. I work full-time, but my evenings and weekends are free. I'm also an early bird, so pre-work visits are also possible. I have a monthly bus pass, an e-scooter, and a car, so it will be no problem for me to get to you! I will treat your beloved pets like they are my own! We will adhere to the same schedule/regimen/rules they live by when you are home.

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Chestnut Hill dog parents share their Rover experiences

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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!

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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 :)

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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.

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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.

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

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!

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Ted C.
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!

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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.

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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!

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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.

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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

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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!!

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Emma
Drop-In Visits
5.0 out of 5 stars

Traci came by for a meet and greet with my family and dog, then it seems like everything went well with the drop in!

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Candice B.
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!

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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.

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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.

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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!

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Ashley W.
Drop-In Visits
5.0 out of 5 stars

Natasha was Great! She watched over our 4-month old puppy while we went out on our own for the first time. She got him through the whining and right into playing, training and resting. She took pictures, and gave us a thoughtful report on what she saw, based on her experience in training dogs. Highly recommended!

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Andrew M.
Drop-In Visits
5.0 out of 5 stars

Nina was wonderful with our shy puppy. She knew exactly how to approach him and gain his trust, and they became instant friends! Nina was also very communicative and flexible when we had a scheduling issue come up. I would definitely book her again.

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Raquel R.
Drop-In Visits
5.0 out of 5 stars

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! 🐾

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Briana M.
Drop-In Visits
5.0 out of 5 stars

Wendy was able to help us out in a pinch and provided the exercise and companionship that Annie needed, while also focusing on safety and health. We would be glad to hire her again!

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Chris G.
Drop-In Visits
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Dog Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Chestnut Hill dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Chestnut Hill.

Rover makes it easy to find Chestnut Hill dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.