Dog Walking Chestnut Hill

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

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Over 103
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: Jessica W.
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Jessica W.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
• 83 reviews
22 repeat clients
10 years of experience
Chesterfield, VA, 23832

“Jessica did a great job walking our Australian Shepherd! It was my first time using Rover and she made it super easy. She was right on time, professional, and friendly. Will definitely be reaching out to Jessica next time I need helping walking my dog! Thanks Jessica!!”

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Annie N.
Sitter Profile Image: Emily H.
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Emily H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 136 reviews
11 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: Sara M.
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Sara M.
from
$30
per walk
5.0 out of 5 stars
• 33 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: Janini C.
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Janini C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 30 reviews
13 repeat clients
8 years of experience
North Chesterfield, VA, 23236

“Kiki had the best time with Janini. Pick and drop off was perfect, she was nice and sleepy when she got home. She can’t wait for her next visit with Mrs Janini!!”

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Kristin C.
Sitter Profile Image: Eileen C.
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Eileen C.
from
$22
per walk
5.0 out of 5 stars
• 75 reviews
24 repeat clients
20 years of experience
Midlothian, VA, 23112

“Eileen and her husband are very kind people. My pup loves them and did great on the first walk! Will definitely book again.”

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Emily A.
Sitter Profile Image: Bruce S.
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Bruce S.
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: Tara W.
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Tara W.
Star Sitter
from
$16
per walk
5.0 out of 5 stars
• 64 reviews
10 repeat clients
10 years of experience
Chesterfield, VA, 23832

“Tara responded immediately to a last minute request to walk my dog two days later so that I could be away for a day. Everything went very well!”

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Jennifer W.
Sitter Profile Image: Hanna C.
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Hanna C.
from
$18
per walk
5.0 out of 5 stars
• 40 reviews
13 repeat clients
10 years of experience
Westover, Richmond, VA, 23225

“I have used Hanna many times for drop-in visits and dog walking due to my very busy work schedule. She always sends photos and makes sure Monty has a full bowl of water and food. She was also able to come by urgently to help barricade him back in the house when he got out accidentally one day. I would 100% recommend her and will continue to use her when needed!”

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Alicia B.
Sitter Profile Image: Katherine L.
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Katherine L.
from
$18
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
3 years of experience
Bon Air, VA, 23235

“Katherine was great and our pup loved her! She is on time and very communicative. She also reinforced skills we practice when walking our dog. We’ll definitely use Katherine again!”

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Anne L.
Sitter Profile Image: Ytalo B.
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Ytalo B.
from
$22
per walk
4.7 out of 5 stars
• 6 reviews
3 repeat clients
6 years of experience
Midlothian, VA, 23112

“Ytalo took great care of our pups while we were gone for the weekend. We loved all the pictures and he kept us updated the whole time. Would definitely schedule with him in the future.”

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Danna M.
Sitter Profile Image: Amanda W.
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Amanda W.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
• 63 reviews
17 repeat clients
15 years of experience
Chesterfield, VA, 23832

About: Hello there! I absolutely adore animals. I spent 3 years at the SPCA, working directly with the animals and fostering. My friends and I started our own rescue, SFC Virginia Animal Rescue. I know how hard it is to trust your dog is in good hands, and to feel happy, and safe. I love snapping photos and sharing with you all that me and your fur baby do during our visit, (and not afraid to inspect poop to ensure your pet is healthy and report when a concern.) My dogs have been through various trainings and would be happy to share my knowledge while I spend time with your pet. I have over 5 years experience with pets with medical needs varying from administering sub-q fluids to medications to inhalers for the cat-kiddos. My girl has hypo-thyroid and has to take a pill twice a day. With my experience with medically-needy animals I am hyper aware of the smallest changes in behaviors in a short period of time and can offer varying tricks with administering for the ones who aren’t big fans. Side note: I do have travel minute limit, for those east of 95, that is within the time limit if the $5ish toll is taken, otherwise it would take over 30 mins. If you are okay with an additional charge of $6 to cover toll, I will be more than happy to assist! I work from home so I get a lot of quality time with my babies. Where I see opportunities to train, I take advantage. Training is a daily on going activity. My animals eat twice a day on snuffle mats with a kibble and veggie/fruit medley. In short, pet care is part of my routine. When hired to do check-ins I like to spend my first time with the pet observing knowing I’m a stranger and I want to not overwhelm. I will read the vibes and either interact more or keep a distance depending on their body language and how they are reacting to me. I know pets sometimes have a tendency to be more reserved or hesitant to do their normal activities. I try to connect and bond during this time as well with treats (if provided) and positive quiet communication.

Sitter Profile Image: Cynthia S.
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Cynthia S.
from
$16
per walk
5.0 out of 5 stars
• 31 reviews
7 repeat clients
17 years of experience
Richmond, VA, 23235

About: I have experience for being responsible for animals my whole life. I have 15 pets of my own and love the responsibility. I enjoying interacting with animals and giving them my full attention. Weekly I care for my own pets and would love to care for yours as well. There isn’t anything I’m not willing to do in caring for your pet. Right now I’m off from work in the summers and have a lot of time on my hands. I will follow detailed instructions on how to handle your animals and what you want to be done. I will always put their safety first and will keep that in mind at all times.

Sitter Profile Image: Brevin B.
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Brevin B.
from
$16
per walk
5.0 out of 5 stars
• 5 reviews
2 repeat clients
15 years of experience
Richmond, VA, 23225

About: I’ve taken care of cats and dogs growing up and have worked with a variety of ages from puppies to elderly. I have 2 years of experience volunteering as a veterinary shadow intern and have confidence to providing for the needs of cats and dogs of all personalities. As a recent college graduate I have flexibility and time to reliably work as needed to provide care for pets. My schedule allows me to prioritize their routines, whether it’s daily visits or last minute bookings. I prefer to adapt approach to pets according to their needs, whether it’s calm and non confronting to shy cats or running with younger dogs. I also like to continue their routines that they are comfortable with. For owners, I keep regular updates as wanted to keep peace of mind.

Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$22
per walk
5.0 out of 5 stars
• 48 reviews
20 repeat clients
20 years of experience
Chesterfield, VA, 23234

“Great to work with Rebecca! Excellent communication and arrived in the agreed time frame with no issue. She took my pup with hers for a walk to the nearby dog park. Pics showed how delighted he was with the walk and the company! Definitely plan to work with her again”

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Christine H.
Sitter Profile Image: Amanda & Matthew F.
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Amanda & Matthew F.
from
$25
per walk
5.0 out of 5 stars
• 8 reviews
25 years of experience
Midlothian, VA, 23113

About: I have had my own dogs since my early 20’s, and I’d probably have about ten more if I could. Everyone in our family has dogs, ranging from tiny Yorkipoos to big ol’ lab mixes, and I love them all! I currently have one rescue pup, Russell, who is 19 different breeds! I am patient, I don’t get grossed out easily, and I will love your pup like it’s a member of the family. My husband and I are both teachers, so we are home full-time during the summer with our two teenage kids. During the school year we work, but I’m usually home by 3:30. Our 13-year old daughter is interested in pursuing a career working with animals, so she will be assisting in the care of your pet. We have a large fenced yard and a dog-friendly house. We even have a doggie door for pups to come and go outside to the back yard as they need or want to. We have one 5-year old dog who gets along great with other pups. Usually when we dog sit, we have the visiting pup have a home base in our daughter’s room where they can be fed separately, have peace and quiet, and enjoy the best air conditioning in the house! We are a dogs on furniture house, and she even loves to let the dogs we are sitting sleep in her bed with her if they want. Your dog should expect many pets and snuggles at our house! If we are coming to your house, we will follow whatever routines and rules you’ve established for your pet. But still expect lots of love for your pet!

Sitter Profile Image: Jenelle J.
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Jenelle J.
from
$25
per walk
4.9 out of 5 stars
• 15 reviews
4 repeat clients
15 years of experience
Richmond, VA, 23235

“We love Jenelle! She does a great job reinforcing what we are working on in training. We are so appreciative of her!”

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Kelly C.
Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$30
per walk
4.6 out of 5 stars
• 11 reviews
1 repeat client
23 years of experience
Richmond, VA, 23235

About: I have lived in a golden retriever family my entire life, and dog-obsessed honestly does not do me justice! I know the Richmond area well and love taking dogs to new locations, like dog parks or the river. Since I am an athletic individual I can offer rigorous exercise for even large active dog breeds. I am very trustworthy and responsible, I schedule my time wisely and am always on time for scheduled appointments. I do work full-time, but am often available on evenings and weekends. I would love the opportunity to get to know you and your dog! I work full time, so I am usually busy during the day. However, I am often free on evenings and weekends and love walks and drop in visits. I do not bring dogs to my own home, because I have older goldens at home. But I love to come spend time where your dog is comfy!

Sitter Profile Image: Alison S.
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Alison S.
from
$32
per walk
5.0 out of 5 stars
• 12 reviews
1 repeat client
21 years of experience
Midlothian, VA, 23114

About: 20+ years caring for dogs and cats. I’ll care for your pet with love and attention, just as I would my own. Experienced with rescue and pure breds, as well as senior dogs and cats. Have cared for small, mid, and large sized dog breeds, such as golden retrievers, goldendoodles, labs, beagles, Cavapoo, terriers, English and French bulldogs, and pugs. I work remotely, so will keep your pet company during day and have plenty of time for walks and play time. I'm available on weekends for boarding at your house, walks and play time. Offering pet sitting at your house, will follow your wishes and needs for your pet (ie, crate or no crate, food timings, and minimum # of walks, etc.

Sitter Profile Image: Nathan C.
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Nathan C.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
• 12 reviews
5 repeat clients
16 years of experience
Midlothian, VA, 23113

About: I’ve rescued/raised three dogs from about 2 months old, and fostered pups/kittens as well. I currently work as Foster Coordinator at a local humane society. I have access to good walking trails, and a dog park. I can keep your dog active with hikes and parks, or we can just chill. Whatever they need! I’m working part-time with a consistent schedule. With advance notice I can be available almost any time, and be able to care for your dog throughout the day. Available for house/dog-sitting anytime. I’m available for anything your dog needs! I enjoy the outdoors, so we can go on walks/hikes together and play at the park. Or if your pup is more the indoor type, we can lounge about and play in the home.

Sitter Profile Image: Sarah H.
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Sarah H.
from
$30
per walk
5.0 out of 5 stars
• 1 review
18 years of experience
NORTH CHESTERFIELD, VA, 23235

About: I have grown up with dogs and cats since infancy and I started petsitting professionally for neighbors, friends, family and others at age 12. Now, I love providing petsitting, dogsitting and petcare services for animals on the side. I have two well-behaved indoor cats of my own and they have many "cousins" (my mom bred Shelties and currently owns three, in addition to a kitten and my sister has a rescue pup). I have fostered moms with kittens from the SPCA. I am patient, kind, loving and caring for furry-faced friends brings me much joy and fulfillment! I currently take care of my best friend’s Maine Coon when she is out of town and on weekdays, I let out and play with her Corgi and lab puppy mid day. I also Petsit for neighbors as needed and have long term relationships with families whose dogs and cats I have taken care of for going on 6+ years! I work full time but it is regular 9-5 Mon through Fri hours and it is a remote job so I work from home. I am available in the mornings, evenings, weekends, holidays and can check in on pets during the day if needed. I have petsat for many folks while working full-time without any issues, and have already established a great routine for petsitting while working remotely! I live in a spacious two bedroom, two bathroom apartment. I have two friendly, well-behaved indoor cats who are familiar with dogs, cats and pets and have had foster cats, kittens and dogs in our apartment with no fights or problems! We do not have a yard, but the apartment is pet-friendly, in the suburbs, in a safe neighborhood and has lots of sidewalks, grassy areas and space for dog walking, etc. There is even a fenced-in dog park a minute from our apartment, in the complex! :) Our apartment is clean, spacious and has plenty of blankets, furniture and space for fuzzy-faced kiddos! I work full time but remotely and it’s easy for me to fit pet care into that routine! Having a flexible schedule allows me to work around your pets’ needs! I am flexible and am comfortable caring for your fur baby in my home or yours! Have provided both services over the years. Just let me know what best suits you!

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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

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5.0 out of 5 stars

Cant be happier with the overall experience. Very easy to work with, very responsive and great for a last minute booking! 10/10

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Justin A.
Dog Walking
5.0 out of 5 stars

Janini walked Emily on her own today. Emily loves her and I feel grateful to have Janini as my dog walker. She arrived on time and gave me feedback about the walk.

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Gisele P.
Dog Walking
5.0 out of 5 stars

I can’t say enough good things about Caitlyn. My Goldendoodle is a little wild (okay, a lot wild), and she handled him with patience and confidence on their 30-minute walk. My Goldendoodle came home happy and tired, which is the best compliment I can give! If you have a high-energy pup, Caitlyn is the walker you want. I’ll definitely be booking her again.

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Chris M.
Dog Walking
5.0 out of 5 stars

Sarah was wonderful! Loved all the pictures and updates. Even though it was our first time using Rover, Sarah put our dogs at ease.

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Danna M.
Dog Walking
5.0 out of 5 stars

Kristy was great! Very comfortable with our big dog! We look forward to more walks with her in the future!

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Megan R.
Dog Walking
5.0 out of 5 stars

Wesley was Fabulous with our dogs Dega and Ripley. He spent a lot of time with them and gave them lots of attention. This is what I want in a Dog Sitter / Walker.

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Brigitta Sylvia S.
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

Jessica did a great job walking our Australian Shepherd! It was my first time using Rover and she made it super easy. She was right on time, professional, and friendly. Will definitely be reaching out to Jessica next time I need helping walking my dog! Thanks Jessica!!

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Annie N.
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

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
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How to book dog walking

  1. 1. Search

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Popular requests for dog walking - Chestnut Hill

Select a filter and find qualifying sitters offering dog walking.

Sitters in Chestnut Hill average 3
repeat dog walking clients

FAQs for Dog Walking - Chestnut Hill

Frequently asked questions about Rover

The average cost of Dog Walking in Chestnut Hill is $18 per walk as of November 2026. Most bookings cost between $16 and $28 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 2,347 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 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 bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Chestnut Hill after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the 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:

  • 91% of walkers can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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