Dog Walking Five Points

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

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Over 198
pet parents in Five Points have booked dog walking

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1 / 1
Sitter Profile Image: Kaylyn M.
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Kaylyn M.
from
$23
per walk
5.0 out of 5 stars
35 reviews
22 repeat clients
25 years of experience
Glacier Ridge, Madison, WI, 53719

Kaylyn is wonderful!! She is very quick to respond when I message her. She keeps me updated on how my dog’s walk are going and I love getting a picture from the walk. My dog Raven loves when Kaylyn comes to visit. I would highly recommend Kaylyn!!!

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Cori L.
Sitter Profile Image: Austin C.
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Austin C.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
73 reviews
29 repeat clients
5 years of experience
Madison, WI, 53719

Austin has been great with my dog, Jax. He's punctual, communicates well, and takes Jax's needs as an old dog into account, taking it slow with him and giving him breaks in the hot weather!

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Andrew W.
Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
137 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

Michelle did an excellent job. When we first met, she took notes about my requests. She followed my directions precisely and took excellent care of Myla. I received updates before, during, and after Myla's walk and she left very thorough notes on the visit card. I highly recommend Michelle.

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Lawrence O.
Sitter Profile Image: Becky P.
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Becky P.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
18 reviews
8 repeat clients
20 years of experience
Verona, WI, 53593

Becky was great! She hopped on a video chat with me prior to meeting my pup and was very communicative and reliable! I would definitely contact her to walk my puppy again!

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Elaina S.
Sitter Profile Image: Daniel & Penny B.
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Daniel & Penny B.
from
$14
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
50 years of experience
Glacier Ridge, Madison, WI, 53719

Highly recommend Daniel and Penny for your dog walking! They were very flexible and went the extra mile walking our dog- literally! Even the small things like making sure he had enough water when he came back were taken care of.

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Joseph B.
Sitter Profile Image: Carmen & Brian W.
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Carmen & Brian W.
from
$16
per walk
5.0 out of 5 stars
18 reviews
3 repeat clients
15 years of experience
VERONA, WI, 53593

About: We will welcome your dog into our family while you are away. My husband and I both work from home, and one of us is here at most times on weekdays. . Our beagle/ heeler mix (Obi) loves to play in our fenced yard, and then settle in for a long nap on one of the big dog beds in my office. Obi was born Jan of 2018. We also have 2 cats, Milo and Potato awho re used to being around dogs, and love to play chase all around our house. Your dog will be treated like a part of our family while in our home, or if we are walking / checking in at your house. We accept puppies who may need more frequent potty breaks, as well as older pets who may need medications, or special feeding. Since I work from home full-time, hanging out with pets is a huge perk of my day! I'm easily able to step away between calls and meetings for potty breaks and playtime. Plus, my husband works hybrid, so one of us is almost always home to keep your pet company. I have a fenced yard, one dog and 2 cats. So, your pet will have plenty of buddies to hang out with and tons of safe, supervised space to relax.

Sitter Profile Image: Annalesse B.
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Annalesse B.
from
$18
per walk
5.0 out of 5 stars
4 reviews
5 years of experience
Madison, WI, 53719

About: I’m a lifelong animal lover, experienced pet owner, and former veterinary assistant who cares for both dogs and cats. I understand how important it is to find someone trustworthy, attentive, and patient with your pets. I’m comfortable with walks, feeding routines, playtime, cleanup, and providing lots of love and attention while you’re away! 🐾 I work full-time during weekdays, so my availability is mainly evenings and weekends. I’m fully available on weekends for walks, drop-ins, and extended care, and I’m happy to help provide reliable, loving care around my work schedule. Your pet’s safety and comfort are always my top priorities. As a former veterinary clinic assistant and experienced pet owner, I pay close attention to routines, behavior, and any special care instructions to help your pets feel safe and stress-free. I’m attentive, reliable, and committed to providing a calm, loving environment.

Sitter Profile Image: Jennifer B.
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Jennifer B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
18 reviews
4 repeat clients
12 years of experience
Middleton, WI, 53562

Jennifer was great with my big, goofy mastiff-pitty mix! And Jupiter/JuJu loved his walk and sniff time with her…he came back ready for a nap! Glad to have Jennifer on board as part of Jupiter’s team!

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Elaina M.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
123 reviews
46 repeat clients
10 years of experience
Madison, WI, 53719

Ann was very responsive and gave updates and photos of the dogs while we were gone. She was flexible with scheduling and accepting a last minute booking.

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Christina R.
Sitter Profile Image: Hanna P.
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Hanna P.
from
$16
per walk
5.0 out of 5 stars
1 review
1 repeat client
6 years of experience
Madison, WI, 53719

About: I grew up with two dogs and have owned guinea pigs for the last 6 years. I volunteer with a shelter where I walk and play with dogs. I also foster dogs with my rescue but do not currently have a foster. I currently work a full time job. I am available for lunchtime walks or enrichment. I am available during the evenings and weekends to care for your dog whether that’s walks, enrichment, or overnight sitting. I’m currently living in an apartment so any sitting would need to occur at your home! I can easily follow any directions you have to ensure your furry friend is well cared for. I’m looking forward to help with your needs. Please reach out with any questions!

Sitter Profile Image: Becky & Judd W.
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Becky & Judd W.
from
$15
per walk
5.0 out of 5 stars
30 reviews
4 repeat clients
3 years of experience
Fitchburg, WI, 53719

About: Our kids LOVE dogs, they pretty much live for them. We can't have our own right now, so we want to love on yours while you're away! We've owned our own dogs, and both of the adults grew up taking care of and loving dogs. We're happy to help reinforce any training that you're doing with your pup! We work during the week, but we can spend the weekend giving full-time care to your dog! We are open to watching your pup during the week, but they would be home alone from about 9am-4:30 pm. Just send me a message if you need longer care than the weekend and we can discuss details! We have a fenced backyard with plenty of room for dogs to run and play fetch. We can offer plenty of outside time and bathroom breaks, we're happy to keep your pet on their typical schedule!

Sitter Profile Image: Magan E.
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Magan E.
from
$18
per walk
5.0 out of 5 stars
33 reviews
14 repeat clients
13 years of experience
Madison, WI, 53719

Magan is great with my dogs! She is punctual and takes them for a nice long walk everyday! Will definitely continue to use her services and highly recommend.

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Marisa B.
Sitter Profile Image: kylie l.
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kylie l.
from
$22
per walk
5.0 out of 5 stars
87 reviews
26 repeat clients
1 year of experience
Madison, WI, 53719

Polite, professional, treats the pupper well, very patient. Easy to work with

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Leah D.
Sitter Profile Image: Anaya S.
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Anaya S.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
41 reviews
14 repeat clients
10 years of experience
Fitchburg, WI, 53719

Anaya was wonderful with our two dogs. She was always on time and provided timely responses to questions and updates on our fur babies. We would love to have her take care of our dogs again!

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Matt H.
Sitter Profile Image: Jacob T.
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Jacob T.
from
$25
per walk
5.0 out of 5 stars
18 reviews
6 repeat clients
12 years of experience
Verona, WI, 53593

Jake to great care of our older rescue dog during a drop in visit and walk. He is really caring and very responsive to request. I highly recommend Jake!

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Kathleen M.
Sitter Profile Image: Matthew H.
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Matthew H.
from
$12
per walk
4 years of experience
Madison, WI, 53719

About: I’m a passionate dog lover who believes pets are family. As a dog owner for over four years, I understand the care, attention, and love our furry friends need every day. Whether you need help with walks or companionship for your pet, I’m committed to providing reliable and caring support. I love dogs of all sizes and personalities and look forward to helping keep your pet happy, safe, and active! While I am looking for a new full time job, I have a lot of availability for anyone needing some help. Would be open to daily walks or as needed. I would care for any pet like they are my own! I am extremely protective of my dog and would only want the best for her and I would offer the same level of care for your pet, too!

Sitter Profile Image: Emily O.
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Emily O.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
14 reviews
2 repeat clients
20 years of experience
Fitchburg, WI, 53719

About: My family dog, Midnight, is a rescue black lab and was a reluctant, anxious leash walker for many years. She has given me experience with “sniff walks”, dog-led walks, treat reinforcement, and various types of collars & harnesses. Today, she is fully comfortable on a leash and we regularly walk 2-3 miles at a brisk pace. My goal is to provide a comfortable and safe experience for your dog at their pace. I would love to spend time with your dog and provide the same level of care as I do for my own! 🐾 I’m a teacher and am available after school hours for drop in visits and dog walking during the week (Mon-Fri). My schedule is more open on the weekends and I can offer my services morning, afternoon, or evening time. I prioritize your pet’s safety with attentive care, secure handling, and clear routines. You can trust me to be reliable, communicative, and respectful of your home. I provide a calm, positive environment where your dog feels comfortable, exercised, and genuinely cared for during every visit or walk.

Sitter Profile Image: Lilly W.
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Lilly W.
from
$15
per walk
5 years of experience
Fitchburg, WI, 53719

About: I love dogs! I grew up with dogs, as well as have a wide range of experience with caring for puppies, senior dogs, and dogs with disabilities. My apartment at this moment does not allow for dogs, so I really am looking for some dogs to give some tender loving care to in the meantime! I am a teacher, so I am free afternoons and evenings, as well as weekends! I am a teacher- so afternoons and evenings, as well as weekends work for me! During the summer, I have a lot more flexibility as well. I am currently offering drop-in visits, as well as dog walking! I am looking for dogs to love on, as I can not have my own in my current apartment.

Sitter Profile Image: Jesse T.
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Jesse T.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
26 reviews
10 repeat clients
1 year of experience
Madison, WI, 53719

About: I have experience working at Paw Pals taking care of cats and dogs. I have also raised and cared for hamsters, horses, birds and bunnys. I'm currently working part-time to only care for animals so I have plenty of time for your animals! Let me know when you need me and I will be there! They will get the time they need. ❤️ Your pet will have the whole downstairs to themselves and lots of play space. I have two friendly cats that are willing to be friends with your pets but they will be upstairs. There are multiple grassy areas to run around in around my condo and trails to walk your pet that will allow them to play in. Treats treats treats❣️

Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
133 reviews
53 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra has been walking our mastiff and doing a great job working on leash skills. We got Bixby as a rescue so he’s needed a lot of extra TLC to relearn things at 3-4 years old. Allegra totally gets him.

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Emily B.
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The median cost per walk for dog walking in Five Points is CA$20

Dog parents share their Rover experiences - Five Points

1 / 1
5.0 out of 5 stars

Meeting Natalie was a pleasure. Warm charming personality. Followed through on questions promptly, on time. Highly recommend Natalie. In future will request her again.

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Dennis R.
Dog Walking
5.0 out of 5 stars

Sidney is absolutely amazing and I highly recommend her! She is really good at communicating and sent the best pictures of my dog when I was missing him. She was willing to give medications and did a great job overall.

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Gracelyn F.
Dog Walking
5.0 out of 5 stars

Krishna was an amazing dog walker and extremely helpful! She was super flexible with a last minute scheduling issue when we needed to add another pet to the walking schedule. She made our wedding weekend extremely smooth with no worries about our pets!

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Michael Y.
Dog Walking
5.0 out of 5 stars

Krista does such a great job with my pets! So happy she is here to give them attention when I can't.

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Donna S.
Dog Walking
5.0 out of 5 stars

Austin was really great to work with and super flexible. He made it really relaxing while I was away knowing my pup was well taken care of, and I will definitely be using Austin again. Thanks Austin!

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Isaac W.
Dog Walking
5.0 out of 5 stars

Highly recommend Daniel and Penny for your dog walking! They were very flexible and went the extra mile walking our dog- literally! Even the small things like making sure he had enough water when he came back were taken care of.

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Joseph B.
Dog Walking
5.0 out of 5 stars

Michelle is very courteous and my dog loved being walked by her. Michelle was respectful of my home, and I would highly recommend her to everyone.

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Sara W.
Dog Walking
5.0 out of 5 stars

Sydney was awesome! Reliable and friendly. I really liked that she reached out to me to let me know that she was planning on walking Myla and had not forgotten the reservation a few days before the reservation went into affect. She took great care of Myla. I highly recommend her!

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Lawrence O.
Dog Walking
5.0 out of 5 stars

Jordan is an amazing dog walker! My dog loves him. He is reliable and really considerate of the dog’s walking experience. He gets to know the dog and what the dog needs. Every time my dog returned she was calm, happy and had a big goofy grin on her face. We had difficult weather during the week he walked her and he was great about communicating with me to work around the weather and make sure she had a great walk. I highly recommend him!

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Natasha M.
Dog Walking
5.0 out of 5 stars

Laura is always so accommodating and kind! We’re so lucky she was able to help us with a last minute request!

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Wesley S.
Dog Walking
5.0 out of 5 stars

Grace is amazing!! She is super nice during our every encounter. She shares lots of pictures for during her walk with my dog. It was truly great having her as my dog walker.

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Maggie L.
Dog Walking
5.0 out of 5 stars

Kira is communicative and so nice to book with. She always takes great care of Lily and takes the time to write a detailed Rover Card.

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Jon S.
Dog Walking
5.0 out of 5 stars

Claire was amazing! She was so friendly, and easy to coordinate with, and arrived in a timely manner . You can tell she really loves dogs. Bella was tired after the walk, which was much needed after being home alone today. Would recommend Claire for anyone in the Madison or Sunprarie area with pups in need of a good walk!

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Damanique F.
Dog Walking
5.0 out of 5 stars

We have a great experience as a first-time Rover user! Magan was reliable and punctual, showing up right on time every day for our pup’s 30-minute walks. I especially appreciated the photo updates and detailed potty reports - it gave us peace of mind knowing how everything went while we were away. Would absolutely book with her again.

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Megan S.
Dog Walking
5.0 out of 5 stars

James was extremely kind and easy to work with! Knox enjoyed his time with James on their walk, which was evident through the pictures and how tired out he was.

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Sara G.
Dog Walking
5.0 out of 5 stars

Becky is reliable and very responsive to communication! I felt very comfortable, coordinating dog walks with her and taking care of our pup!

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Jonathan M.
Dog Walking
5.0 out of 5 stars

This was my first time using Rover and I’m very happy with the process. Azaria was wonderful to work with!

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Jason G.
Dog Walking
5.0 out of 5 stars

Here’s a shorter version: --- Melissa is a fantastic dog sitter! She communicates clearly, sends great updates, and is genuinely thoughtful about my dog’s needs. I always feel at ease knowing my dog is with her. Highly recommend!

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Mitchell R.
Dog Walking
5.0 out of 5 stars

Michael was nice, attentive, professional and on time. This was the first time we hire someone else to walk our dog Rocoto and he loved Michael. We appreciate his responsiveness and the pictures updates. At the end Rocoto was safe and happy and that gave us a piece of mind. We are looking forward to hire his services again.

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katia r.
Dog Walking
5.0 out of 5 stars

Isabel is a great communicator! She is amazing with my dog Gimli and lets him come to her. She asks amazing questions and is so sweet. Definitely rebooking.

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Gracelyn F.
Dog Walking
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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

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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

    Schedule a free in-person Meet & Greet to find the perfect fit
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Sitters in Five Points average 3
repeat dog walking clients

FAQs for Dog Walking - Five Points

Frequently asked questions about Rover

The average cost for Dog Walking in Five Points on Rover is $19.98 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 1,478 sitters on Rover offering Dog Walking across Five Points. 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 Five Points. 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 Five Points.

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 Five Points. On Rover:

  • 90% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 98% 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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