Dog Walking Chestnut Hill

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Over 107
pet parents in Chestnut Hill have booked dog walking

Chestnut Hill, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Francoise S.
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Francoise S.
from
$15
per walk
5.0 out of 5 stars
40 reviews
13 repeat clients
30 years of experience
Midlothian, VA, 23114

Francoise was great! She worked well with our crazy schedule and was very personable. She was thorough and efficient as well. We enjoyed working with her and look forward to working with her in the future.

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Ashley W.
Sitter Profile Image: Jessica W.
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Jessica W.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
82 reviews
22 repeat clients
10 years of experience
Chesterfield, VA, 23832

Jessica‘s walked my dog several times now. She always shows up exactly what time she says she will be there and does a great job with my dog. I’ll be using her more in the future.

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Clifford A.
Sitter Profile Image: Kassandra J.
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Kassandra J.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
91 reviews
17 repeat clients
26 years of experience
North Chesterfield, VA, 23236

Kassie put in the extra effort to make my grumpy little old man of a dog happy! She consistently put in extra time to ensure his comfort and to keep me posted while I was away. Very appreciative of her!

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David A.
Sitter Profile Image: Kiara P.
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Kiara P.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
253 reviews
70 repeat clients
4 years of experience
Midlothian, VA, 23114

Kiara was extremely reliable and patient with both of my dogs. One has a neurological condition and Kiara was able to handle her with grace. Would highly recommend and use again.

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Rochelle R.
Sitter Profile Image: Wesley H.
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Wesley H.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
18 reviews
5 repeat clients
20 years of experience
Midlothian, VA, 23112

Wes was great! Was comfortable around my dog immediately, which made her accept him right away. He was punctual and sent photo updates. Highly recommend!

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Tiffany S.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
319 reviews
86 repeat clients
30 years of experience
North Chesterfield, VA, 23236

Excellent and reliable care! DAMACIA was available with short notice planning and ensured that Bear got everything he needed. She even made sure he got excellent care on the rainy day and bear, like most pups, is not a fan of the rain. I highly recommend DAMACIA and will book with her again when I’m looking for help!

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Kyle W.
Sitter Profile Image: Julia H.
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Julia H.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
44 reviews
18 repeat clients
16 years of experience
North Chesterfield, VA, 23236

Julia did an amazing job keeping my puppy busy while I was in a meeting. She is very reliable and I would definitely book again. I loved seeing the pictures and that she included a write-up of all the fun things they did together.

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Erin D.
Sitter Profile Image: Jynette V.
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Jynette V.
from
$15
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
30 years of experience
Chesterfield, VA, 23832

Got along very well with my mini poodle, she may be his new best friend 🧡 they did great together from the moment they meet at the meet and greet, she did an awesome job

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Cristina C.
Sitter Profile Image: Kristy B.
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Kristy B.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
318 reviews
123 repeat clients
16 years of experience
Chesterfield, VA, 23832

Exceptional care!

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Tracie F.
Sitter Profile Image: Kaylee K.
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Kaylee K.
from
$20
per walk
5.0 out of 5 stars
55 reviews
25 repeat clients
5 years of experience
midlothian, VA, 23114

Kaylee is ANAZING!!! She is super creative and intuitive in how she is interacting with my puppy. She has been helping keep him exercised during the day and during the day but due to his age, he can’t walk far distances. She fills in the rest of the time with both physical and mental stimulation, including play, puzzles, and cuddles. I can’t recommend her more highly!!!

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Amira T.
Sitter Profile Image: Alyssa H.
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Alyssa H.
from
$16
per walk
6 years of experience
Richmond, VA, 23235

About: I have experience caring for highly energetic dogs including two of my own as well as experience with many cats, so I understand the importance of patience, consistency, and attentive care. My responsibilities include daily feeding, exercise, playtime, and monitoring their overall health and well being. I'm comfortable following care instructions and providing plenty of attention to help pets feel safe, happy, and well cared for! I bring the same level of dedication and compassion when caring for others animals. I work 7:00 a.m. to anywhere between 11 a.m. and 3:00 p.m. which leaves flexibility to fit your animals scheduled needs, with my days off varying each week. I'm available for overnight house sitting and can provide care before and after work, including feeding, walks, playtime, and plenty of attention. On my days off, I have more flexibility for extended visits and one on one time with your pets, please reach out and I can provide my off days for the week! It's my priority to keep your pets on their normal routine and provide dependable care while you're away, along with regular updates for your peace of mind!! I genuinely enjoy caring for animals and treat every pet as if they were my own! I understand that each animal has its own personality, routine, and needs, and how important it is to take the time to make them feel safe, comfortable, and loved. Whether it's feeding, walking, playing, basic care, or providing companionship, I am dependable, patient, and attentive. My goal is to give pet owners peace of mind, knowing their fur family members are in caring and responsible hands!

Sitter Profile Image: Ytalo B.
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Ytalo B.
from
$18
per walk
4.5 out of 5 stars
5 reviews
2 repeat clients
5 years of experience
Midlothian, VA, 23112

About: Hi there! I’m Fabrizio, proud dog parent to Bruno, my 5-year-old buddy who taught me that every pup has their own personality and needs. Over the years I’ve also cared for the pets of friends and family — from playful puppies to older dogs that just need extra love and attention. I’m flexible, reliable, and love keeping owners updated with pics and messages. With me, every walk is an adventure and every cuddle feels like home. 🐾🐶 I work as an independent sports agent, which means most of my job is done from my phone and laptop. Because of this, I have a very flexible schedule and can easily adjust my day around walks, drop-in visits, or pet sitting. Whether it’s mornings, afternoons, evenings, or even weekends, I can usually make it work. I’m happy to discuss your pet’s routine and find the perfect times to keep them happy and cared for. Your pet’s safety is always my top priority. When I’m in your home, I respect your space and follow all instructions carefully to make sure your pets feel comfortable and secure. I treat every house as if it were my own, with responsibility and care. On walks, I’m always alert to surroundings, traffic, and other animals. I keep dogs safely leashed, avoid risky situations, and make sure they get exercise in a fun but safe way. You can trust that your pets will always be in good hands with me.

Sitter Profile Image: Mary M.
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Mary M.
Star Sitter
from
$14
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Richmond, VA, 23235

About: I am very chill and upbeat. I just truly love animals and love caring for them. I’ve grown up around pets my whole life, I’ve never lived without a dog. I’m very very available! I will happily dedicate all my time to your fur baby and give them all the attention they deserve and need. I am very attentive and will follow your routines for your pets with care. I know how important it is for some pets for things to go as usual, and I will be very sure of that.

Sitter Profile Image: Bruce S.
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Bruce S.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
29 reviews
10 repeat clients
7 years of experience
Richmond, VA, 23236

Bruce is great. He showed up minutes before the appointed time to be certain he was not late. He thrilled the dogs with their first ride in a convertible. He sent plenty of pictures including those that look like the dogs are smiling ear to ear. He was prepared with water during the walk and gave them breaks to rest from the heat. Our yellow lab is usually restless and constantly pulling my husband but she behaved for Bruce. I would highly recommend him.

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Kathy C.
Sitter Profile Image: Kristina & Richard T.
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Kristina & Richard T.
from
$20
per walk
5.0 out of 5 stars
2 reviews
20 years of experience
Midlothian, VA, 23114

About: We (myself and my husband, Ricky) are pet lovers and currently have two "wobbly cats". They don’t freely roam the house due to their wobbly condition and the stairs, so we are able to keep visiting pets separated. Our beloved dog passed away a few years ago and we have had cats ever since. Our kids are 9 and 8, and love to help. I am home full time with the kids, but occasionally Ricky will take the lead on pet sitting in our home. I am home with my kids this summer and our days are filled with a balance of fun and responsibility. We are very flexible with our time, and able to help. We have a fully fenced in back yard. We have chickens in our backyard but they can be kept up in their run if needed.

Sitter Profile Image: Frances A.
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Frances A.
from
$17
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
37 years of experience
Westover, Richmond, VA, 23225

About: I've never not had animals in my life! I spent my early years on a working farm and have always had a way with animals. Dogs love me (cats, too!) and I them ❤️ I have many years of experience in the veterinary field and know what to do in emergencies. I am currently working part time and my schedule is flexible. I do work away from home for 5-8 hours a day, split shift. I have dogs amd cats but can keep them separate, if necessary. My dogs are dog friendly, although my beagle mix is very bossy (typical!) Dogs will be in the house with my dogs, but they can be separated, if needed. I can crate, if the parents supply the crate. Dogs will be leash walked in the wide front yard but we can also go across the street to the dog park, too!

Sitter Profile Image: Finneas B.
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Finneas B.
from
$16
per walk
8 years of experience
Richmond, VA, 23236

About: I’ve taken care of friends’, family’s, and neighbor’s pets since 2018. I love getting to know other pets and see what makes them special. Above all else, I prioritize their safety and happiness like they’re my own pet! I am available at any time to give your pet a potty break, a walk, whatever they need! I am available for boardings as well. I go back to school in August so if you have any summer vacations lined up, I will gladly take care of your furry friend. I have a chocolate lab puppy who is 5 months old. I walk her multiple times every day and play with her extensively. I never get tired of being her playmate and I would to provide the same service to your pup! I have had another dog and cat before her as well. With at least one pet around the house I’ve been caring for my own pets since I can remember.

Sitter Profile Image: Sara M.
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Sara M.
from
$30
per walk
5.0 out of 5 stars
32 reviews
16 repeat clients
8 years of experience
Midlothian, VA, 23114

About: I have always been raised around dogs and love all breeds. A few years ago we adopted our own three- legged mixed pup who has filled our hearts with love! We also have another rescue mix that is high energy and keeps his friends playing all day! They love to play, but also love to cuddle and relax. We have never had trouble with our fur babes getting along with others. We and our dogs love to play and go on walks! We have a nice sized backyard that is fenced in and a great neighborhood to walk in with a park near by. Due to our opposite work schedules someone is almost always home to be with the dogs. We would love to meet your furry friend and let the playing and cuddles begin!

Sitter Profile Image: Emily H.
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Emily H.
from
$30
per walk
5.0 out of 5 stars
135 reviews
10 repeat clients
13 years of experience
Midlothian, VA, 23114

Emily has done a great job walking Teddy while I’m at work. I highly recommend here and I will be using her walking service in the future.

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James D.
Sitter Profile Image: Sherrita D.
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Sherrita D.
from
$15
per walk
10 years of experience
North Chesterfield, VA, 23236

About: I provide your dog(s), or cat(s) the care they need while you're away - right in their own home or mines. I will feed and water your pet; exercise it; administer medicine, vitamins or other special care (shots, pills or drops) as needed and give it lots of love and playtime. I will also look after your home, giving it that "lived-in" look by bringing in mail and newspapers and adjusting lights and blinds. You can return home at any hour of the day or night to find your home and happy pet eagerly awaiting your return. When you call, I will schedule a time to meet with you and your pet(s). This consultation will allow your pets tome and become familiar with my voices and smells. In addition, this will provide time for us to discuss what services you are looking for, feeding/watering instructions and frequency of visits. ******When requesting services, once I accept the booking you have 2 hours to confirm booking or I will decline for the next client******** I am available daily for all your pet care needs; day sittings, dog walking and house visits within my servicing area. Contact me with your pet care needs. I provide your dog(s), or cat(s) the care they need while you're away - right in their own home or mines. I will feed and water your pet; exercise it; administer medicine, vitamins or other special care (shots, pills or drops) as needed and give it lots of love and playtime.

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The median cost per walk for dog walking in Chestnut Hill is $20

Dog parents share their Rover experiences - Chestnut Hill

1 / 1
5.0 out of 5 stars

Janini was wonderful! Very responsive and kept us updated with pictures, in which our girl looked to be having a great time. Would definitely book again. :)

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Caitlin J.
Dog Walking
5.0 out of 5 stars

We reached out to Christell for last minute walks for our senior dog while we were out of town for an evening. She showed promptly for the walks and sent us wonderful updates. Our dog is a little quirky on walks (he freezes) and she figured out a way to keep him moving! We also have a cat at home who got lots of attention. Thank you so much Christell for agreeing to take care of them under short notice! We would highly recommend Christell to take care of your fur babies!

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Katrina G.
Dog Walking
5.0 out of 5 stars

We've had Julia walk our puppy several times now. She does a great job every time. She is very reliable and I love reading her reports after the walk. I highly recommend her for your pet care needs.

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Erin D.
Dog Walking
5.0 out of 5 stars

Wes was great! Was comfortable around my dog immediately, which made her accept him right away. He was punctual and sent photo updates. Highly recommend!

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Tiffany S.
Dog Walking
5.0 out of 5 stars

Sarah is amazing! Took great care of our GSD, including ball play. This is our third time using her and will again anytime we need a dogwakker.

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Delia I.
Dog Walking
5.0 out of 5 stars

Great as always! We have used Caitlyn & Samuel several times and always professional, timely and great communication.

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Nate M.
Dog Walking
5.0 out of 5 stars

Hannah took the time to come and meet our dog prior to walking him for the first time. Really appreciated her going above and beyond! She has a great personality and communicates well!

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Joshua B.
Dog Walking
5.0 out of 5 stars

Ada was a wonderful companion for our dog, Freda. She was punctual and provided the time and exercise Freda needed and certainly enjoyed. I appreciate Ada’s easy approach to Freda and her sweet personality. Would love to request her again in the future!

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Kim B.
Dog Walking
5.0 out of 5 stars

Amber was attentive to our and our dog's needs and was very communicative. She is kind, amenable, and our dog enjoyed her.

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Daniel B.
Dog Walking
5.0 out of 5 stars

Tamiya is excellent! She makes time to meet your pets before being booked and delivers quality services/care.

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Eriqc L.
Dog Walking
5.0 out of 5 stars

Denise was amazing with Shadow. She was always on time with walks and kept me up to date with daily pics and messages! I would definitely use Denise again to take care of my baby!

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IBM4eva
Dog Walking
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  • 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

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  • 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 walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

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Sitters in Chestnut Hill average 3
repeat dog walking clients

FAQs for Dog Walking - Chestnut Hill

Frequently asked questions about Rover

The average cost for Dog Walking in Chestnut Hill on Rover is $17.76 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking 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 Walking. For more information on service fees, click here .

As of July 2026, there are 2,336 sitters on Rover offering Dog Walking across Chestnut Hill. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Chestnut Hill. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Chestnut Hill.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

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.

Every walker 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 .

Yes, you can find walkers who have experience with handling special pet needs in Chestnut Hill. On Rover:

  • 94% of walkers can help with special care needs
  • 98% can help with giving oral medications or injections
  • 99% 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.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.

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 walker.

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