Dog Walking Windsor Hills

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Over 3
pet parents in Windsor Hills have booked dog walking

Windsor Hills, 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: Abby M.
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Abby M.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
288 reviews
103 repeat clients
14 years of experience
Chester, VA, 23831

Abby helped me during a last minute trip. She was pleasant and kept me informed. This was my first time using the Rover App but will be back because of her. Thanks Abby!

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Shameka C.
Sitter Profile Image: Emily W.
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Emily W.
from
$18
per walk
5.0 out of 5 stars
93 reviews
26 repeat clients
1 year of experience
Colonial Heights, VA, 23834

Emily was simply outstanding. She went above and beyond to take care of my dog and kept me up to date on everything happening with her. I would absolutely recommend her 100% to anyone who needs dog care/services!

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Caneel D.
Sitter Profile Image: Amanda B.
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Amanda B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
25 reviews
7 repeat clients
20 years of experience
Chester, VA, 23831

Reagan and Brody enjoy Amanda!

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Beverly W.
Sitter Profile Image: Phyllis N.
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Phyllis N.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
107 reviews
44 repeat clients
50 years of experience
North Chesterfield, VA, 23237

Absolutely amazing experience. Work and day to day has been made so much more enjoyable and I have so much appreciation for the patience my pup is experiencing. I will be a regular for quite some time. Thank you again Phyllis!

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Megan B.
Sitter Profile Image: Crystal C.
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Crystal C.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
299 reviews
106 repeat clients
15 years of experience
South Chesterfield, VA, 23834

Crystal was so accommodating and great with our 2 dogs while I was away. She provided me with updates and made being away from my babies a lot less stressful. We will definitely be booking with her again! Thank you for everything, Crystal!

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Jasmin V.
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
214 reviews
60 repeat clients
10 years of experience
Chester, VA, 23831

Thank you so much for taking care of our dogs again and for doing it on such short notice! It’s so nice having someone so reliable and trustworthy. I know they’re already looking forward to your next visit!

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Jasmin V.
Sitter Profile Image: Darnell M.
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Darnell M.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
101 reviews
38 repeat clients
14 years of experience
Colonial Heights, VA, 23834

Darnell did a great job taking Minnie out for her afternoon walk! Thank you again for taking such great care of our kid, means the world to us that you took care of her like she was yours!

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Sharon L.
Sitter Profile Image: Alecia B.
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Alecia B.
Star Sitter
from
$13
per walk
5.0 out of 5 stars
59 reviews
20 repeat clients
20 years of experience
Chester, VA, 23836

Alecia is always so good with Karma. She is easy to do business without. She is prompt in response, schedule and she follows instructions exactly. Thank you Alecia!

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Debbie S.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
50 reviews
14 repeat clients
15 years of experience
Chester, VA, 23831

Sabrina did an excellent job of gaining the trust of my dogs! They enjoyed the walks very much.

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Lecia J.
Sitter Profile Image: Michelle H.
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Michelle H.
from
$25
per walk
5.0 out of 5 stars
11 reviews
6 repeat clients
25 years of experience
Chester, VA, 23831

About: I have a lot of knowledge with most exotics as well, I’m happy to help with any bird, turtles/tortoise, fish, snake, any lizard, monkeys, any rodent, rabbit, chicken, horses, pigs, cow, goats and sheep. I’ve taken care of animals my entire life. I also work with The Wildlife Center and do some small animal rehabilitation. I currently have 2 dogs and one fish. I’ve recently fostered 3 tortoises, a senior dog and a bearded dragon. I am able to do some puppy training and very knowledgeable in senior care for dogs and cats. I am currently a stay at home mom and my kids are in school full time. I have my real estate license as well as degree in pharmacology but I’d much rather work with animals at my own pace. I have a decent sized fully fenced in backyard. I am also able to crate your animals if that is something that is preferred. My dogs are extremely sweet and love to play with all of their dog friends that come to visit. They are up to date on all vaccines and my house is very clean but pet friendly. My couch is big enough for all the pups and people here.

Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
6 reviews
7 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

Allejah was great . Ciroc really enjoyed her . She kept me updated and I felt safe leaving my dog with her. I would highly recommend!

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Janayla W.
Sitter Profile Image: Melissa M.
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Melissa M.
from
$25
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
30 years of experience
Chester, VA, 23831

About: I've cared and been around pets and dogs of all breeds all my life. My family has always had dogs so I have experience feeding, grooming, playing, walking, administering simple medication, and basic training. I'm a mom of 7 that works part-time, with little ones in school, so I have the means, time, professionalism, and drive to play and care for your four legged family member, when your unavailable to.... And your able to rest assure that they are well taken care of :) When caring for pets I am able to visit and care for them in their natural setting.... Of their home, so they more natural and relaxed. Please reach out if your interested in weekend boarding at my home.

Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$25
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Chester, VA, 23831

About: I specialize in dogs that need a little extra grace and a lot of patience, but I also love a social butterfly! Having raised a reactive high-drive mix and managed the pulling power of large breeds like Labs and Great Danes, I know firsthand that not every dog is an easy walker. I bring a calm, highly disciplined, and observant approach to every visit, ensuring your dog feels secure and understood. ​My Special Skills Include: ​Reactive & Anxious Dog Handling: Creating safe, low-stress environments for sensitive souls. ​High-Drive Breed Management: Experience safely handling and exercising powerful, high-energy working breeds. ​Behavioral Reinforcement: Utilizing consistent treat training, professional handling techniques, and keen observation of canine body language. ​Large Breed Experience: Confident leash-handling for strong pullers. ​Whether your dog is a socialite who loves making friends or a sensitive pup who needs a sitter with unshakeable patience, I tailor my approach specifically to them. Pet care isn't just a part of my routine—it is my full-time dedication here in the Temple area beginning mid september! As the owner of A&A Professional Pet Care, my schedule is built entirely around providing your pets with the absolute best care and companionship possible. Here is what I can provide for your furry family members: ​Reliable Midday Care (9 AM - 6 PM): I am available Monday through Friday to provide the perfect midday break for your pet, whether they need an engaging walk, a fun drop-in, or just some focused playtime while you work. ​Early Morning Adventures: I am wide awake and ready to provide early 5:00 AM or 6:00 AM walks to get your pup's day started off right with plenty of exercise before you head out the door. ​Weekend Coverage: I offer weekend care on a select, rotating basis, providing you with trusted pet sitting or drop-in coverage for those busy Saturdays or quick weekend getaways. ​Consistent, Recurring Schedules: I specialize in setting up recurring weekly schedules for drop-ins and walks, providing your pets with a consistent best friend and giving busy working parents total peace of mind. Whether I’m staying at your place or visiting for a drop-in, your pets are treated like family. My approach combines physical exercise with mental engagement—I love incorporating short, positive training sessions into our day to keep their minds sharp. They’ll get plenty of 'tummy rub' downtime and scheduled feedings, but they’ll also get the structure and play they need to stay happy and tired out. Your dog won't just be watched; they’ll be active, engaged, and thoroughly spoiled.

Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$25
per walk
5.0 out of 5 stars
29 reviews
12 repeat clients
23 years of experience
Chester, VA, 23831

Tiffany is amazing! She goes above and beyond. This is truly her passion. She loves what she do and it shows. This is my third time using Rover and she is the best one we booked for our Buddy. Tiffany, I hope you are available whenever me and my family decides to travel.

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Nancy W.
Sitter Profile Image: Sarah K.
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Sarah K.
from
$20
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Chester, VA, 23836

About: I promise you trust, communication, comfortability, and great care! I love pets! I grew up with a Golden Retriever named Skippy! I now own my beautiful mut mix of Lab, Pit and Blood Hound. His name is Maverick! He's 2 and such a loving, happy dude! I currently dog sit my mom's 3 Boston Terriors whenever she needs to go out of town and have been since I was a teenager. I also take in my best friend's older pit bull, Cookie, and her and Maverick get along wonderfully! There's plenty of space to walk dogs around my apartment community, along with a fenced in tennis court area where they can run free! I work full time AT HOME so I'm flexible just looking to make some extra money I work from home Monday through Friday, and am available most weekends, so I have lots of time and flexibility to care for your doggos! I live in an apartment but it's very dog friendly! I will ensure your dog gets lots of attention and love! I have access to lots of trails, open pet areas, and a fenced in tennis court where they can run free and we can play fetch! My dog is very friendly and has lots of experience around other dogs. I do have a large dog crate if that is required or necessary.

Sitter Profile Image: Lashell D.
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Lashell D.
from
$35
per walk
5.0 out of 5 stars
32 reviews
6 repeat clients
15 years of experience
Chester, VA, 23831

Friendly and sweet. She is timely and bonded wit my dog.

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Deanna E.
Sitter Profile Image: Lindsey R.
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Lindsey R.
from
$18
per walk
5.0 out of 5 stars
9 reviews
4 repeat clients
2 years of experience
Chester, VA, 23831

About: I love dogs, they are my favorite people. All shapes and sizes, whenever I spend time with them, they just make my heart happy. When they’re with me they’ll be taken good care of. Whether it’s long walks, games of tug of war, endless belly rubs, and lots of cuddles. I will love your pet as if they were my own. In addition to raising two dogs of my own, I’ve cared for friends and neighbors’ pets while they’re at work or away. I know how hard it is to leave your pet behind whether it’s while you’re at work or on vacation but when they’re with me you won’t have to worry because they’ll be well cared for and loved. I work full time Monday through Friday from 8am-5pm but only live 5 minutes from my work. I am able to go home midday and have evening and weekends free to spend lots of time with your fur babies. I make sure that they will remain on they’re regular feedings and pawty schedules and are free to run the apartment if no need to crate. My apartment provides a fenced in yard for them to have safe and fun outdoor time. I work full time Monday through Friday from 8am-5pm. I am able to have evening and weekends free to spend lots of time with your fur babies. I will make sure that they will remain on they’re regular feedings and pawty schedules and are free to run the house if no need to crate. My house provides a fenced in yard for them to have safe and fun outdoor time.

Sitter Profile Image: Grace L.
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Grace L.
from
$20
per walk
5.0 out of 5 stars
39 reviews
14 repeat clients
17 years of experience
South Chesterfield, VA, 23834

Grace was friendly and showed up when scheduled.

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Rayanna B.
Sitter Profile Image: Nadra W.
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Nadra W.
from
$21
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
12 years of experience
Chester, VA, 23836

Thank for being available last minute.

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Patrícia Z.
Sitter Profile Image: Brooklynn B.
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Brooklynn B.
from
$20
per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
10 years of experience
South Chesterfield, VA, 23803

About: I love all animals but I’m a dog lover through & through. Yes.. Even the stinky butt, stinky breath, so ugly that they’re cute, accident prone, jumper, barker, puller, escape artists, babies too. I was raised with 2 boxers who have made their way across the rainbow bridge. I raised a super mutt for 6 years who has also crossed over. I now have a Rottie mix who was adopted through Chesterfield Animal Shelter going on 4 years ago. She is, in addition to my human babies, my dog child. She is the best of friends with my kids. If you ask my oldest how many brothers and sisters he has, she is included in his total … 😂 I have 10+ years of experience walking/pet sitting neighbors, family and friends dogs but im in my second year of pet sitting full time. I can’t express enough the joy it has brought me. I’ve worked with puppies, seniors & everything in between of all sizes. I’m familiar with giving oral medication and have learned how to properly perform CPR on dogs. I fully understand & respect that each animal is different & has their own needs and personality. As well as their owners. This is why my care goes beyond maintaining. I’m full of patience and love & It’s important to me that i strive for comfortability. I have taken on pet sitting full time! My regular returning clients are a priority but i still have plenty of open room for new clients! I understand that for each pet, their wants and needs may vary. I am big on respecting what makes everyone the most comfortable and cared for. I strive to leave your pet feelings enriched and at ease by the end of my visit.

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The median cost per walk for dog walking in Windsor Hills is $20

Dog parents share their Rover experiences - Windsor Hills

1 / 1
5.0 out of 5 stars

Emily is super attentive and even remembered part of our dogs’ routines I forgot to mention! We think she’s great!

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Alic B.
Dog Walking
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Meet local walkers who will treat your dogs like family

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Popular requests for dog walking - Windsor Hills

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Sitters in Windsor Hills average 3
repeat dog walking clients

FAQs for Dog Walking - Windsor Hills

Frequently asked questions about Rover

The average cost for Dog Walking in Windsor Hills on Rover is $17.76 per walk (as of August 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 August 2026, there are 2,410 sitters on Rover offering Dog Walking across Windsor Hills. 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 Windsor Hills. 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 Windsor Hills.

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 Windsor Hills. On Rover:

  • 94% of walkers can help with special care needs
  • 98% 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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