Dog Walking Sleepy Hollow

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

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Over 35
pet parents in Sleepy Hollow have booked dog walking

Sleepy Hollow, 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: Fred H.
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Fred H.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
3 repeat clients
30 years of experience
West dundee, IL, 60118

“Fred has been an absolute blessing to our family. Moochy like him immediately and trusted him. She’s usually pretty skittish. Fred was always on time, willing to be flexible if needed, and was just really good with Moochy. I needed someone who was strong to walk mooch because she’s big and strong. Fred had no trouble with it. I had absolute faith in Fred’s ability to handle her. And when Mooch saw his car pull up, she was so happy. I have no trouble recommending Fred to be your dog walker.”

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Monica M.
Sitter Profile Image: Derek G.
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Derek G.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 119 reviews
26 repeat clients
25 years of experience
Carpentersville, IL, 60110

“Derek accommodated a last minute walk for our pup, and was very kind and communicative. He took great care with jackson and followed all the instructions I provided him. Will definitely book again!”

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Noreen L.
Sitter Profile Image: Samantha C.
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Samantha C.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 23 reviews
5 repeat clients
4 years of experience
Algonquin, IL, 60156

“Amazing! She helped me feel very comfortable for my first time!”

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Emma O.
Sitter Profile Image: Jennifer T.
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Jennifer T.
from
$25
per walk
5.0 out of 5 stars
• 10 reviews
2 repeat clients
30 years of experience
Lake in the Hills, IL, 60156

“Jennifer is absolutely wonderful, so attentive and thoughtful with our pup. She’s the perfect peace of mind to know our pup is happy, safe and having a great time. Her communication is superb and her kindness is unmatched. So grateful for her!”

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Kortney Geegan
Sitter Profile Image: Marcus G.
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Marcus G.
from
$20
per walk
5.0 out of 5 stars
• 5 reviews
1 repeat client
13 years of experience
Elgin, IL, 60120

“Marcus was patient and kind to Mitchell. He took the time to bond and be comfortable with each other and would hire him again.”

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Ayinde B.
Sitter Profile Image: Miranda N.
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Miranda N.
from
$25
per walk
4.9 out of 5 stars
• 11 reviews
2 repeat clients
10 years of experience
Algonquin, IL, 60102

About: I have been an animal lover my entire life and shown it in the care I give. I started my pet care experience at 14 by watching family members' pets, as well as my mother's coworkers' animals. From there, I expanded into word-of-mouth clients from friends, and finally opened up a Rover account when I entered my 20s. I treat all pets I care for like my own, and have experience with several animals, including dogs, cats, birds, fish, reptiles, small mammals, and even horses. I love learning and continue to expand my knowledge for caring for animals by researching and taking classes where I can. I currently work full time, which is Monday through Thursday from 9:00 A.M. to 6:00 P.M. and Saturday from 10:00 A.M. to 2:00 P.M. I am always willing to work things into my schedule, so please contact me to do so. I love when owners leave me notes regarding their pets care and little trick and habits that will help the pets feel more comfortable. I ensure safety and care to any pets I sit or walk.

Sitter Profile Image: Maya P.
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Maya P.
from
$18
per walk
5.0 out of 5 stars
• 6 reviews
2 repeat clients
4 years of experience
Algonquin, IL, 60102

About: I’ve had a love for animals since I was small. This kept me active as a volunteer in animal shelters throughout high school, in addition to being a reliable sitter for my family and friends’ fur babies. I would love to go on walks and give lots of love to your furry friend(s) whenever you need! Please check my availability through my calendar! I update it consistently. I am full time studying at home postgrad, so I have a very flexible schedule! I will be diligent in keeping your dog safe by walking with a leash and always keeping a close eye on them. I have no other pets at home and am graduated, so your pet will get my full attention.

Sitter Profile Image: Ali S.
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Ali S.
from
$20
per walk
5.0 out of 5 stars
• 32 reviews
5 repeat clients
12 years of experience
Fox River Grove, IL, 60021

“Ali was great!! She did everything I was hoping for and kept me updated! Highly recommend!”

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Karley M.
Sitter Profile Image: Marcy E.
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Marcy E.
from
$20
per walk
5.0 out of 5 stars
• 11 reviews
3 repeat clients
20 years of experience
Crystal lake, IL, 60014

“Marcy is amazing!! My dogs love having her come by, she takes a lot of care with them. She sends photos, gives updates, everything I could ask for!!”

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Bridget K.
Sitter Profile Image: Jacqueline G.
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Jacqueline G.
from
$20
per walk
10 years of experience
Elgin, IL, 60123

About: I've taken care of both kitten and puppies to a senior dog. It's been a very rewarding opportunity to gain trust from my pets and the pets in my family. I'm patient, caring, and responsible. I work a full time job 9-6pm Monday through Friday. I'm available on weekends, I'll be able to care and walk for most of the day. Keep routine as much as possible, I know it will depend on the pet but my goal is to keep them calm and happy just like any other day.

Sitter Profile Image: Lydia F.
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Lydia F.
from
$22
per walk
5 years of experience
Algonquin, IL, 60102

About: I’m a caring and dependable person who genuinely enjoys spending time with dogs. I’ve cared for my friend’s dog while they were away on vacation, including making sure they were fed, walked, comfortable, and given plenty of attention and companionship. I understand how important it is to know your dog is in good hands while you’re away, and I’ll treat every dog I care for with the same patience, attention, and care I would want for my own. My schedule is currently very flexible, which gives me plenty of availability for walks and dog care during the week and on weekends. I’m typically available mornings and afternoons and can be flexible depending on your dog’s routine and needs. I’m happy to care for your dog in the comfort of their own home and follow their normal routine. I can take them on walks, play with them outside, give them plenty of attention and companionship, and keep them active throughout the day. With the owner’s permission, I’m also happy to take them on outings to places like Petco or the dog park. My goal is to make sure your dog feels comfortable, happy, and well cared for while you’re away.

Sitter Profile Image: Erika G.
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Erika G.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 312 reviews
86 repeat clients
25 years of experience
St. Charles, IL, 60175

“Erika is so wonderful! She always takes wonderful care of our buddy and makes she he gets all that he needs while we are away. She’s awesome!”

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Abby B.
Sitter Profile Image: Joanna M.
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Joanna M.
from
$20
per walk
1 repeat client
30 years of experience
Pingree Grove, IL, 60140

About: I am new to professional pet care, but I have a genuine love for animals and enjoy spending time with dogs. I am responsible, patient, and attentive to each pet’s needs. I am excited to provide safe, caring dog walks and drop-in visits and treat every pet like my own. My work schedule varies from week to week but I’m flexible and always make time for pet care. I’m usually able to fit in dog walks and drop in visits on most days, depending on timing. I enjoy being active and spending time with pets, so I will do my best to accommodate requests and keep communication clear. Your pet’s safety and comfort are my top priorities. I provide a calm, attentive presence during walks and drop-in visits, making sure each dog feels secure and cared for. I stay alert to surroundings, use safe handling practices, and always respect each pet’s individual needs and personality.

Sitter Profile Image: Katrina M.
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Katrina M.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 12 reviews
4 repeat clients
22 years of experience
Crystal Lake, IL, 60014

“Thank you 🙏🏽”

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Britto T.
Sitter Profile Image: Alexis M.
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Alexis M.
from
$17
per walk
4 years of experience
Elgin, IL, 60120

About: As a dedicated pet sitter, my commitment goes beyond basic care. I bring a unique set of skills and a genuine love for animals that ensures your pets receive the highest level of attention and care. I understand that every pet has its own personality, preferences, and needs. I take the time to get to know each pet individually, tailoring my care to ensure they feel comfortable and loved. I believe in keeping pets active and entertained. Whether it’s playing fetch, going for walks, or engaging in interactive toys, I make sure your pets have fun and get the exercise they need. My schedule is flexible during the weekend During the week I’m not available in the morning but I am flexible in the afternoon or if we need to add another week day. I am well-versed in pet first aid ensuring your pet’s safety at all times. I also keep a close eye on their health, looking out for any signs of distress or illness.

Sitter Profile Image: Stephanie B.
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Stephanie B.
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
5 repeat clients
1 year of experience
Hampshire, IL, 60140

About: Hi there! My name is Stephanie and have ample experience and tons of love for dogs! We have rescued a few pups with varying personalities and support requirements from partial paralysis, fear-aggression and anxiety. I have experience in dog walking, boarding and administration of medications (our own pup takes meds daily). I do have a 2 year old toddler at home along with an 11-year-old dachshund mix so any boarding requests should take that into consideration and will be vetted accordingly! I do work from home so your love bug would get lots of attention !

Sitter Profile Image: Linda C.
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Linda C.
from
$25
per walk
4.8 out of 5 stars
• 6 reviews
4 repeat clients
7 years of experience
Schaumburg, IL, 60193

“Friendly and great with dogs. Did a good job walking ours.”

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Shanthi-Sree N.
Sitter Profile Image: Eloise L.
Verified Enhanced Background Check
Eloise L.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 17 reviews
3 repeat clients
15 years of experience
Huntley, IL, 60142

About: I live in an apartment and am unable to keep a pet due to the lease conditions. This has left me with a hole in my heart for connection with pets. I would adore the opportunity to spend time with your pet and care for them. Growing up, we had a yellow Labrador Retriever named Sandy who I felt was the best dog we could possibly have asked for. I trained her, taught her tricks, and played with her almost constantly. In more recent years, I took care of Daisy who was a medium sized mixed breed with spunk. She belonged to an ex-partner and I cared for her as if she was my own. She needed lots of stimulation and outlet for energy as well; we had multiple walks a day and it was fun to see her solving playful challenges I made. I grew up around rabbits that I adored, and even dressed them up in my doll’s clothes! My sister and I later raised rabbits for several years. We brought them everywhere we could and had special harnesses and leashes to walk them around the neighborhood or pet store, etc. They also liked to run around our backyard with our dog. I am comfortable around cats, hairless or not! I allow them to approach me, rather than crowd their space. When they want to, I love cuddling with cats and feeling them purr. I have usually cared for multiple cats at once. Although I have never lived with a cat, I am confident in caring for them and interacting with them. My roommate has six ferrets and they each hold a little piece of my heart. I give them medication when she is stuck at work late, and let them out to play. They are such curious and playful little creatures! Staying late at the office? Let me stop by to feed, pet, play with, and exercise your pet. No time in the early mornings or during lunch? Let me take the time you wish you had to care for them. While my own home is not pet friendly, I am happy to visit yours. If your pet has a routine and schedule they are on, I want to keep that seamlessly running for you. If your pet is adventurous, I want to keep them engaged.

Sitter Profile Image: Anna S.
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Anna S.
from
$25
per walk
4.9 out of 5 stars
• 11 reviews
3 repeat clients
9 years of experience
Elgin, IL, 60123

“Anna is a great dog walker! She always letting me know if there any issue with our dog. I also, love that she send pictures of our dog on his walk. I hope we continue working with her.”

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Samantha T.
Sitter Profile Image: Joseph S.
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Joseph S.
from
$25
per walk
5.0 out of 5 stars
• 4 reviews
10 years of experience
Lake in the Hills, IL, 60156

“Joseph arrived early for his appointment and was great with the dogs. He asked about their special needs and took them for a grand adventure around our neighborhood. I will use him again and I recommend him.”

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Lynn G.
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The median cost per walk for dog walking in Sleepy Hollow is $20

Dog parents share their Rover experiences - Sleepy Hollow

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5.0 out of 5 stars

We are so grateful to Maggie for taking such wonderful care of our dog(american bully)! Our pup always gets so excited when it's time for their walk. Maggie is reliable, punctual, and truly cares about animals. Highly recommend to anyone looking for a great dog walker!

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Galina S.
Dog Walking
5.0 out of 5 stars

Cat is our go to sitter my boys are very happy to see her and she loves seeing them. Genuinely caring,helpful and great communication with us during her care.

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Nidia T.
Dog Walking
5.0 out of 5 stars

Jacqueline and Uriel are great, highly recommend. They always take good care of my dachshund Ladybug and are very communicative. Lots of pics and video updates. Ladybug loves them. 🐶💕

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Robin M.
Dog Walking
5.0 out of 5 stars

Amanda is the best! She is always on time, super easy going and flexible, responsive, and kind! She has made having a puppy so easy while we are at work. She has not only been great for us, but our puppy absolutely adores her. Thank you as always Amanda!

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Sarah G.
Dog Walking
5.0 out of 5 stars

Fred has been an absolute blessing to our family. Moochy like him immediately and trusted him. She’s usually pretty skittish. Fred was always on time, willing to be flexible if needed, and was just really good with Moochy. I needed someone who was strong to walk mooch because she’s big and strong. Fred had no trouble with it. I had absolute faith in Fred’s ability to handle her. And when Mooch saw his car pull up, she was so happy. I have no trouble recommending Fred to be your dog walker.

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Monica M.
Dog Walking
5.0 out of 5 stars

Iryna is awesome! She does such a great job and our puppies love her! She is trustworthy and quickly responsive. She is flexible and always on time. Totally recommend!

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Sarah G.
Dog Walking
5.0 out of 5 stars

Jessica has walked my dog numerous times and has done a great job! My dog likes her and she is easy to work with!

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Ava N.
Dog Walking
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book dog walking

  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.
  3. 3. Book & Pay

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Popular requests for dog walking - Sleepy Hollow

Select a filter and find qualifying sitters offering dog walking.

Sitters in Sleepy Hollow average 4
repeat dog walking clients

FAQs for Dog Walking - Sleepy Hollow

Frequently asked questions about Rover

The average cost of Dog Walking in Sleepy Hollow is $19 per walk as of October 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 October 2026, there are 6,620 sitters on Rover offering Dog Walking across Sleepy Hollow. 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 Sleepy Hollow. 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 , 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 Sleepy Hollow 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 , 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 .

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

  • 88% of walkers can help with special care needs
  • 92% can help with giving oral medications or injections
  • 95% 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 .

walkers on Rover set their own , 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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