Dog Walking Windsor

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

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Over 7
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Windsor, 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: Stephanie C.
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Stephanie C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
267 reviews
94 repeat clients
15 years of experience
Augusta, ME, 04330

Stephanie was extremely accommodating as I prepared to move into a new home. She was extremely warm and always made sure my boys were comfortable.She made sure my pets got the attention they needed while I was at work and I’ll always appreciate it during this busy time! Thank you again!

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Brooke H.
Sitter Profile Image: Eúde M.
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Eúde M.
from
$20
per walk
1 year of experience
China, ME, 04358

About: I've always had pets in my house so what sets me apart is the constant, undivided attention your pet will receive. Because I work entirely from home, your dog will never be left alone for long stretches or have their routine disrupted. I naturally integrate frequent potty breaks, midday play sessions, and mental enrichment into my daily workflow. This high-availability setup is ideal for anxious pets, young puppies who need constant supervision, or seniors requiring frequent outdoor trips. I also work with someone at a few locations near wayne. therefore, I am available on certain weekdays from 10am to 4pm on mondays, and I can work all day on saturdays. Be honest I can't bring others dogs into my house, cause my dog is a bit agressive toward other dogs, tough overly friendly with people.

Sitter Profile Image: Lindsay S.
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Lindsay S.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
195 reviews
76 repeat clients
25 years of experience
Whitefield, ME, 04353

About: Professional Groomer, trainer, accepting pets in home for extended stay. Farm, fence, full play room, individualized care, puppies and aged dogs welcome! It’s a dog’s life 🐾 Full availability, 7 days a week - holidays included! Active home with quiet spaces and experienced care. Full care and integration into our daily routine if it works for your pet - we’re up early, and on the go - lots of socialization (or not, if that’s your pups jam!) play, enrichment time and experiences. This is my full-time commitment and passion. My background includes Grooming, Training, Seminar’s in dog behavior, pet CPR and first aid, and running a large boarding and grooming facility. I am Licensed by the State of Maine for boarding 🐾 I utilize a lot of tools to keep everyone happy, healthy, and safe - kennels, gates, double leashes, double fencing, cameras (indoor and out!) and a very specific routine that I have found works for this little home. Please be aware - dogs need to be kennel trained to board here. I DO use them at feed time, and for nap times as needed, to keep all the dogs in my care safe. I ask that you send your dogs meals pre-packed, or in a reasonable (for their stay) container. Please leave “favorites “ that cannot be replaced at home. This includes beds! I provide fresh, daily, clean toys and blankets, plus raised cot beds. Feed time is 2X per day, with 2X per day “stimulation” snacks prior to nap time. I provide all snacks, but need to know if your pup has a special diet. If your dog has separation anxiety, I really need to know. It doesn’t mean I won’t take your dog, but it DOES mean I have to structure things differently for that particular stay, and rates will be discussed. My own dog has SA, so I understand; I just need the information to plan accordingly.

Sitter Profile Image: Saber H.
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Saber H.
from
$15
per walk
5.0 out of 5 stars
2 reviews
5 years of experience
Chelsea, ME, 04330

About: I’ve taken care of all sorts of animals since I was very young. I’ve been officially working in pet sitting for five years. Animals usually love me, and I’m willing to be as pateint as needed for the ones who are more shy and may take longer to warm up. I move at there speed. I also make sure that your house stays in the same condition you left it in. Maybe even cleaner lol. There’s no need for you to come home to a messy house after a much needed vacation. Leave the stress to me. This has become my full time job as well while I begin to build my writing career. So I am available for you whenever you may need me. I have an extremely flexible schedule and can accommodate your needs. I would love to have a meeting where we go over all your expectations and needs, every person is unique in how they care for there pet. I aim to make this process as easy as possible. I’ll bring a note pad and you tell me all the details of there regiment. I will follow them to a T and give you live updates on your little friends whenever you need!!

Sitter Profile Image: Sarah W.
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Sarah W.
from
$25
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
Augusta, ME, 04330

About: I have had dogs and taken care of dogs and cats since childhood. In my more recent years I have dog sat for family members and neighbors. I have enjoyed being able to give peace of mind to them knowing their pets are safe, happy, and cared for. Owning a dog and cat myself I understand the stress and fear of having to leave your pets. Whether it’s work, vacation and other life events it can feel like you’re leaving a piece of your heart behind while you’re away. I strive to bridge that gap and be able to provide peace of mind. My dog is a rescue and came to me with some behavioral challenges: fear, reactivity, resource guarding and separation anxiety. Since being with me he is a thriving boy with manners and is learning new skills and tricks every week! That being said I don’t scare easily and have experience managing a variety of behaviors. I know from experience leaving a pet that has some big feelings at times can be even more challenging and thats where I come in. To offer you peace of mind knowing your dog or cat will be safe and cared for with me. I firmly believe in the saying no bad dogs and would love to get the opportunity to take one worry off your plate while you are away! I have summers off and am able to be around as much or as little as needed for your pet in the summers as that is a busy time for vacations. I do structured schedules with play, train walk and rest times with pets. I can also create scheduled enrichment times throughout our time together. I try to cater what we are doing based on needs of the dog so they are fulfilled.

Sitter Profile Image: Liseli M.
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Liseli M.
from
$32
per walk
4.9 out of 5 stars
46 reviews
13 repeat clients
4 years of experience
South China, ME, 04358

Liseli is an incredible walker. Any time I leave bonito in her care he has such a wonderful time and I know he's in good hands ✨

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Aiden T.
Sitter Profile Image: Gabrielle B.
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Gabrielle B.
from
$20
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
20 years of experience
Augusta, ME, 04330

Highly recommend! Gabrielle has been wonderful with our pup, great communicator and very consistent.

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Chelsey E.
Sitter Profile Image: Melanie M.
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Melanie M.
from
$20
per walk
22 years of experience
Augusta, ME, 04330

About: I have been a vet tech for 22 years and am looking for something I can do to be with my family more. I am great with cats and dogs of all ages, sizes and personalities. I have owned cats, dogs, hamsters, rats and rabbits. My schedule would be based on the individual needing pet care. Communication is very important to me and a successful pet sitting experience. I do have children that my schedule would be based around. I am well educated on animal handling and care. Working as a vet tech has given me ample experience in all situations regarding health, behavior and affection.

Sitter Profile Image: Nathan B.
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Nathan B.
from
$20
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
15 years of experience
Augusta, ME, 04330

About: Ever since the family cat had kittens when I was four years old, I have been drawn to the care of animals. Honoring the lives of pets as our friends has been a source of inspiration and therapy for myself personally. As a working artist, taking the time to care for animals has been such a privilege and the perfect change of pace while I continue to work on creative projects. I have a German Shepherd that I keep separated from the work I do with other animals. I am located at a small farmhouse in Augusta that has a huge yard with two a-joining fields. There is more than enough room to explore the surround with your pet. I am also an avid walker so exercise is big for me generally.

Sitter Profile Image: Ascher t.
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Ascher t.
from
$15
per walk
25 years of experience
Vassalboro, ME, 04989

About: Hi! I’m a lifelong animal lover with experience caring for a wide range of pets, including dogs, cats, and horses. Growing up around animals has given me a deep understanding of their needs, personalities, and behaviors. I’m attentive, patient, and committed to making sure every pet feels safe, comfortable, and loved while you’re away. Whether it’s going for walks, playtime, or just providing companionship, I treat every animal as if they were my own. I’m also experienced in administering medications and can confidently follow any specific care instructions to ensure your pet stays happy and healthy. You can count on me to provide reliable, compassionate care and plenty of updates so you have peace of mind while you’re away! Pet care fits naturally into my routine, especially during evenings and weekends when I’m most available. I make it a priority to be there for pets when their owners are busy, traveling, or just need an extra hand after a long day. I’m consistently available for evening drop-in visits, making sure pets are fed, exercised, and given plenty of attention and companionship before settling in for the night. On weekends, I have even more flexibility and can accommodate multiple visits, extended care, or last-minute bookings. Caring for animals is something I truly enjoy, so I build my schedule around giving them the time, consistency, and care they deserve. I tailor my care based on each pet’s needs and the service requested, whether I’m in my home or yours. My goal is always to keep pets comfortable, safe, and as close to their normal routine as possible. In a client’s home, I focus on maintaining your pet’s usual schedule feeding, walks, playtime, and any special care instructions so they feel secure in their familiar environment. I keep things clean and organized, and I’m respectful of your space while making sure your pet gets plenty of attention, affection, and exercise. I also provide regular updates and photos so you always know how your pet is doing. If caring for pets in my home, I provide a calm, safe, and pet-friendly environment where they’ll receive lots of supervision, love, and attention. I make sure they have a comfortable place to relax, consistent potty breaks, and plenty of playtime. I’m attentive to details and experienced in administering medications if needed, and I’m always mindful of each pet’s personality, energy level, and comfort. My priority is making sure every pet feels happy, safe, and well cared for while you’re away.

Sitter Profile Image: Chloe S.
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Chloe S.
from
$17
per walk
6 years of experience
Augusta, ME, 04330

About: I have experience with animals from Great Danes to Fancy rats. I have training experience as well with things such as potty training, walking etiquette, and a few show tricks. I have college classes in the afternoons but my mornings and nights are wide open on weekdays. As for weekends its just dependent on the day so I'll need advanced notice. I have a small yard, and within a quarter mile from the nearest park. I can give potty breaks ever hour if need be, and I'm great at matching an animals energy level.

Sitter Profile Image: Falisity H.
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Falisity H.
from
$25
per walk
5.0 out of 5 stars
4 reviews
20 years of experience
Farmingdale, ME, 04344

About: Iv been raising newborn kittens and fish my entire life. I grew up with big dogs too! Past co-workers would often say I have a funny personality and a calm demeanor. My attention to detail is my strongest skill. I have done volunteer work for camp sunshine, the animal refugees, and we run a youth group called Gaming for Christ. Im an artsy person; im in college for horticulture and I hope to work as an agricultural specialist. Veterinary assistant experience from York County Community College. I have five years of customer service experience. Looking for long-term work with friendly people who will make a list of specific details (if needed) for your pets. I take a great time making sure your pets are happy and comfortable! Completely open to any time or date that your furry friend needs me! Holidays and special occasions included! Im going to school online so I can always be available. I am very knowledgeable in Pet CPR. Fast reaction skills and attention to detail. Very capable on keeping environment clean and safe for any pet.

Sitter Profile Image: Esther B.
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Esther B.
from
$20
per walk
5.0 out of 5 stars
2 reviews
2 repeat clients
4 years of experience
Gardiner, ME, 04345

About: Hello! I am new to Rover but I have been working with animals all my life from a very young age and I have been pet sitting for about 4 years. There were always pets in the home, mostly dogs and cats all my life and I have thorough experience being around animals and knowing how to take care of them. I took a major part in taking care of the puppies that my family bred most of my childhood, I have experience in working with a variety of animals such as dogs, cats, reptiles, roosters/chickens, horses, guinea pigs, etc. Besides working with my own pets I have been pet sitting for around 4 years now and have become very comfortable working with other peoples pets. I pride myself on my attention to detail and focus on making sure your pet/pets are as comfortable as possible. I am currently a student but most of my classes are online so I am very flexible and available pretty much every day of the week currently. I am able to be intuitive and approach every animal with the care and attention that is specific to their needs. I am sensitive to boundaries and always making sure to focus on listening to what they are communicating.

Sitter Profile Image: Ashley L.
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Ashley L.
from
$26
per walk
5.0 out of 5 stars
3 reviews
22 years of experience
Vassalboro, ME, 04989

Ashley is absolutely wonderful with my dog! She is reliable, caring, and clearly loves animals. My dog was so excited when Ashley came over our meet and greet. I feel at ease knowing my pup is in great hands. Ashley provides updates and photos, which I really appreciate. I highly recommend Ashley to anyone looking for a trustworthy and attentive dog walker!

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Cindy A.
Sitter Profile Image: Heidi T.
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Heidi T.
from
$20
per walk
5.0 out of 5 stars
1 review
1 repeat client
15 years of experience
Pittston, ME, 04345

About: I have owned animals my whole life. Working with dogs is my passion. I have over a year of working with dogs in a shelter setting of all sizes and most breeds. I am fear free certified. I have handled more challenging dogs and really easy dogs. I know how to read a situation and think a head. I’m all about positive reinforcement and fear free. Any questions? I would love to chat! I’m looking to build my own client base from the ground up, working with dogs is my desire. I typically make my daily routine around work. The owners are in control. Tell me your pups needs, and I can provide them! A simple short walk, a hike, dropping in to feed and a quick potty break. I’m open to your needs and wants, do not hesitate to ask.

Sitter Profile Image: Christi C.
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Christi C.
Star Sitter
from
$12
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
20 years of experience
Whitefield, ME, 04353

Through cold and snow- Christy was on schedule to walk and feed our pups. Clear and helpful communications.

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Laura W.
Sitter Profile Image: Eliza S.
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Eliza S.
from
$30
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
30 years of experience
Augusta, ME, 04330

Eliza was responsive and great with my beagles.

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Elissa C.
Sitter Profile Image: Eric B.
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Eric B.
from
$18
per walk
20 years of experience
Augusta, ME, 04330

About: I love dogs 🐶. I have been a dog owner most of my life. I would welcome your dog with open arms. Please feel free to reach out to me anytime- Eric. I’m looking forward to hearing from you soon....My dogs name is Lilly. She’s a beautiful female German Shepherd who loves people and other dogs. I have a very flexible schedule and will get back to you ASAP with any concerns you may have. I’m looking forward to this new adventure for my life. Hopefully, it will be as much fun and a rewarding experience for everyone. We must protect our animals. We are their voice when no one can hear them. Please reach out to me ASAP so we can get started on this new adventure.

Sitter Profile Image: Kelly C.
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Kelly C.
from
$30
per walk
5.0 out of 5 stars
37 reviews
11 repeat clients
40 years of experience
Belgrade, ME, 04917

Kelly took great care of my pups, giving them the exercise and love they needed! Thanks for helping me in a pinch.

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Erika C.
Sitter Profile Image: Erin D.
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Erin D.
from
$35
per walk
4.9 out of 5 stars
21 reviews
5 repeat clients
30 years of experience
Benton, ME, 04901

About: I’ve been taking care of pets since I was a little kid and helped my parents at my uncle’s farm. I truly love all animals and enjoy their individual personalities. I have experience dog/house sitting dating back to 2000 in the Camden area. Since we moved three years ago, I’m looking to meet new clients and help you with your furry loved one in the Waterville area. I worked in animal hospitals in my early 20s so I have a great wealth of knowledge to draw from in many areas (but not exotic pets, as none of the veterinarians I worked with were specialtists.) Currently, I'm available for sitting, dog walking, and drop in visits. I am not working outside of my home right now, so I'm quite flexible for scheduling. Any pet I take care of is treated as if they’re a member of the family. I believe in spoiling pets with love, but keeping the boundaries of the owner so as not to undo any training. Reinforcing good behavior is always a priority.

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The median cost per walk for dog walking in Windsor is $25

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Meet local walkers who will treat your dogs like family

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Sitters in Windsor average 2
repeat dog walking clients

FAQs for Dog Walking - Windsor

Frequently asked questions about Rover

The average cost for Dog Walking in Windsor on Rover is $16.05 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 226 sitters on Rover offering Dog Walking across Windsor. 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. 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.

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. On Rover:

  • 100% of walkers can help with special care needs
  • 100% can help with giving oral medications or injections
  • 100% 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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