Dog Sitting Sleepy Hollow
Book a Sleepy Hollow dog sitter to watch your dog in your sitter’s home or yours.

Over 112 pet parents in Sleepy Hollow have booked dog sitting
Sleepy Hollow, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Pets were well taken care of. He shared pictures (but I did not receive the written reports the sitters usually share after every visit). He helped as possible with cleaning poop/throw up my puppy left around the house. Quick to reply to my text messages.”

“Eloise was fantastic! She followed all of our instructions, and our dog and cat seemed to genuinely love having her take care of them. She was available for a drop in last minute, and sent over very cute photos and videos. Will definitely be hiring her again!”

“Kaileigh was so great to my pups! I was happy to find someone that lived near me. She treated my pups as her own. She kept in contact with me and sent my photo updates, I loved that! I would highly recommend her to watch your furbabies.”

“Leslie took great care of my cats! She gave me thorough updates and asked questions when needed, and made good inroads befriending the cats (even my super-shy one). I appreciate you, Leslie!!”


About: I've been a lifelong dog lover and currently have a Golden Retriever/Irish Setter who keeps me active with plenty of walks, playtime, and adventures. Caring for my own high energy dog has taught me the importance of patience, consistency, and giving each dog the attention they deserve. Whether your pup loves long walks, belly rubs, fetch, or simply having a companion nearby, I'll make sure they feel safe, loved, and comfortable while you're away. I treat every dog as if they were my own and strive to provide the same level of care and affection I'd want for my own pet :) I currently work part-time on some weekends in Huntley, IL (Friday–Sunday), but I’m generally very flexible and available during the week! I just ask for a few days’ notice whenever possible so I can make sure I’m able to give your pet the time and attention they deserve. 😊 I’d also love to set up a meet & greet with you and your fur baby before our first visit! It’s a great opportunity for us to get acquainted, learn about your pet’s personality and routine, and make sure they feel comfortable with me. Your pet's safety, comfort, and happiness are always my top priorities. While I do have a spacious corner lot with a secure tie-out area for supervised outdoor time, the majority of my services take place in your home where your pet is most comfortable and can maintain their normal routine. During walks and drop-in visits, I'll follow all care instructions closely, ensure your pet has fresh water, exercise, potty breaks, playtime, and plenty of attention. I'll treat both your pet and your home with the same respect and care that I would my own, and I'll keep you updated with photos and messages so you can feel confident knowing your furry family member is in good hands.
About: Have owned and cared for dogs and cats for 13 years, care for them like they are my own children. Rely on me to protect and love your pets! I enjoy walking and playing with dogs while conversing with them like friends. I spend most of my time with my pets and make sure to include them in things like running errands so they are not bored. I can do anything to assist any kind of pets and their necessities. Whether medical needs or preferences, you can trust me to follow any instructions needed for your pet. I will do anything to make sure your pet is comfortable and feels safe at all times.
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.
About: Pets have always been a big part of my life, and I care for every animal with genuine love, patience, and attention. I’m experienced with walks, feeding, baths, playtime, and comforting pets who may feel shy, anxious, or lonely. I take my time learning each pet’s personality and routine so they feel understood, safe, and cared for. My goal is for every pet to feel relaxed, protected, and truly loved while their family is away. Pet care is a natural part of my daily routine. I make time every day for walks, feeding, playtime, and giving pets attention and comfort. I’m very consistent and flexible, so I can easily fit their needs into my schedule. Your pet will be welcomed into a loving home with three friendly dogs and a gentle cat who enjoy having company. I always supervise playtime, keep routines consistent, and make sure every pet feels safe, calm, and cared for. I can crate if needed.
About: Hi, I’m Drew! I know how important it is to find someone you can completely trust with your furry family members. I have years of experience caring for dogs and cats. Whether your pet needs high-energy outdoor walks, gentle companionship, or strict adherence to a daily feeding and medication schedule, I adapt my care to fit their exact routine. What I offer: Tailored Care: Flexible scheduling to meet your pet's specific personality and energy level. Communication & Updates: Frequent photo updates, detailed check-ins, and quick response times so you never have to worry while you're away. Safety & Comfort: A calm, attentive environment focusing on behavioral care, and lots of genuine affection. I look forward to meeting you and your pet for a Meet & Greet! Pet care is my top focus every day. Because I work from home, I’m fully available around morning, noon, and night for feedings, energetic walks, potty breaks, playtime, and cuddles. My flexible remote schedule allows me to give your pets frequent, consistent attention and companionship all week long. I maintain a clean, secure, and completely pet-friendly space with zero escape routes and plenty of cozy spots to relax. Whether at my home or yours, I follow your exact feeding and medication instructions, stay vigilant for any signs of stress, and prioritize your pet's physical comfort and emotional well-being above all else.
About: Dogs have been at the center of my life for as long as I can remember. Growing up, my family raised two Bichon Frises who lived long, happy lives to ages 13 and 15. Over the years, I have helped care for a wide range of family dogs, including energetic Border Collies, small Yorkies, and larger rescue mixes. Today, I am the proud owner of Jasmine, a sweet and powerful mix who loves barking at squirrels. Living alongside dogs of all shapes and temperaments taught me how to read their needs and respect their individual routines. I bring that same patience, calm energy, and careful attention to every pet I care for. Whether your dog needs a steady mid-day walk or a quick drop-in visit, I will make sure they stay safe, relaxed, and well loved while you are away. I am currently working part time. Saturday Sunday Monday, then Monday Tuesday rotating. Beginning in April I will have classes Monday-Friday from 9-4. I can be available for overnight stays during the week if your furry friend is okay alone from 9-4. For overnight stays and drop ins I am happy to take dogs with or without fenced in yards on walks whenever your pup wants to!
About: I want to be a vet one day and I have always been the go-to sitter for my family and family friends for years! I love all animals! I am available everyday! I am looking for a steady job right now so I can afford to transfer to ISU from MCC where I currently go! I take my husky for walks as much as she's willing to and she's 13.5! I play with her all day when I am home and I have had tons of ducks and other animals!
“♥️Ashley and Andrew are a very personable and responsible couple that we had the pleasure of hiring for our cat care needs. They took A+ care of our 13 and 3 year old cats. The cats are so happy. We could tell that they were well taken care of and spoiled with attention during our vacation. These two people are high on our list of the very best kind of people that we have met and would most definately rehire. We love the ease of choosing the perfect sitters thru Rover, kind, knowledgeable, people keeping us up to date with every visit with a report and pictures♥️ Very reassuring🤗. Thank you Ashley and Andrew.. we had a wonderful vaca!!”

About: I’ve been a house sitter and dog walker for other people for years, while also taking care of family rescues also! Puppies and kitties of all ages and sizes, from Great Danes to Bichon! I’m currently studying so some fur friends to keep me company are very welcome! My days are very busy, so I’m mostly available on night sits, otherwise drop in sits are good! I’m very attentive and caring, good at cleaning up after the pups and cleaning the house. Walking them and very good about handling strong dogs on walks, never getting angry at them.
About: I provide peace of mind when you need someone you can trust with your pet(s) and home. I am detail-oriented and an excellent communicator who keeps you updated every step of the way. . . . Here is what I bring to your pet's care: • Reliability & Trust: I treat your home with total respect. Whether managing keys, locking up securely, or sticking to precise morning and evening schedules, I am fully accountable. • Specialized Care: From shelter volunteer training to raising large breeds from puppyhood, I understand animal behavior. I am fully experienced with everyday pet needs, frequent potty breaks, and precise food or medication administration for all ages. • Multi-Pet Households: As a proud cat mom, I excel at keeping multi-pet environments structured, peaceful, and clean. . . . Pets naturally gravitate toward my calm, warm energy. Whether your pet loves having a friendly presence around the house, enjoys standard daily exercise, or thrives on a consistent routine, you can relax knowing they are truly cared for. Whether you need a consistent dog walker for your workweek or a dedicated sitter for an upcoming vacation, I am able to plan ahead and be there for you and your pet. I prioritize clear communication and structure my days around your requested schedule. Because I oversee my own weekly routine and keep an organized calendar, I never miss a beat! My Rover availability is always fully updated. I know how important your privacy and peace of mind are. How I care for your space: • Gentle Respect: I treat your home with the utmost kindness and respect, ensuring everything stays clean, secure, and exactly as you left it. • Home Care: I am very mindful of keeping doors locked, windows secure, and your keys safe. • Pet Comfort: I do regular, quiet checks to ensure your pets are happy, comfortable, and safe indoors.
About: Hey, I’m Madison, a reliable and affectionate dog lover based in Barrington! 🐾 I’ve raised two Golden Retrievers and a French Bulldog, and I also have experience caring for abused and rescue animals. That background has given me patience, compassion, and the ability to handle pets with all kinds of needs, from energetic puppies to gentle seniors. I enjoy exploring and would love to give your pet the care & companionship they deserve while providing you with peace of mind. Your pet will always be treated like family in my care. ❤️ As a full-time Master’s student at DePaul, I take night classes Monday through Wednesday from 5:45–9:00 pm. That means I’m free during the day—prime hours for walks, drop-ins, or pet sitting. Thursdays through Sundays, I have even more flexibility, so I can easily work around you and your pet’s needs and routine. Your pet’s safety and comfort always come first. While I don’t provide leashes, I always carry poop bags and will follow your instructions to keep your pet’s routine consistent. If it’s time for a walk, we’ll go, whether that means a quick potty break, a long scenic route, or a trip to the dog park to burn off extra energy. I’m careful to make sure any dogs we encounter are friendly before entering off-leash settings, and if your pet has special needs, I’ll happily adjust our routes or keep to quieter areas. My goal is to make every outing safe, comfortable, and enjoyable for your pet while giving you peace of mind.

About: Hi Everyone! I’m Bailee and I’m obsessed with animals. I’ve had a dog and/or a cat in my life since I was born (or multiples at the same time) - I have 2 cats and 1 dog of my own. I am available for dog walking and house drop ins on Monday, Wednesday, Friday, Saturday and Sundays. Please let me know how I can help you out!! I will either take your dog on a walk as requested or drop in to take care of the animal. I have worked around animals for many years.
The median cost per visit for dog sitting in Sleepy Hollow is $21
Dog parents share their Rover experiences - Sleepy Hollow
This was our very first time using Rover and hiring a dog sitter, so naturally we were a little nervous! However, we couldn’t have been more pleased with our experience! Maddie was always on time, kept us updated, and sent lots of pictures, which gave us such peace of mind while we were away. It was so reassuring to know our dogs were being well taken care of. She made our first experience with Rover a wonderful one, and we would absolutely use her again! Highly recommend Maddie!!

Eloise was amazing with my dog and cat and I know they are in such good hands with her! I really appreciate her flexibility and attention to detail with both of my babies and their various needs. I was able to fully enjoy my time away because I knew they were well taken care of. I will absolutely be booking with her again!

Amanda is the best she’s been doing drop in visits for me for four months now M-F very punctual, great communication, has never canceled or missed a scheduled visit and she treats my dog birdie like her own. Amanda has exceeded all expectations I can’t wright a good enough review for her. Thanks Amanda - Adam & Bird

Iryna took wonderful care of my dog during twice-daily drop-ins. She is warm, friendly, and clearly compassionate — my dog was happy and relaxed after every visit. One afternoon she was about 30 minutes late because her car broke down, but she messaged me right away and kept me updated, so it was no problem at all. I would happily book her again and recommend her to anyone looking for a caring sitter. Thank you, Iryna

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
Book and pay through Rover’s secured platform—no cash or checks required.
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.
How to book dog sitting

1. Search
Browse profiles of sitters near you who offer dog sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog sitting - Sleepy Hollow
Select a filter and find qualifying sitters offering dog sitting.Sitters in Sleepy Hollow average 7 repeat dog sitting clients
FAQs for Dog Sitting - Sleepy Hollow
Frequently asked questions about Rover
The average cost of Dog Sitting in Sleepy Hollow is $19 per visit as of October 2026. Most bookings cost between $15 and $28 per visit. On Rover, sitters 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 6,546 sitters on Rover offering Dog Sitting across Sleepy Hollow. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Sleepy Hollow choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter 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 .
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.
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 sitter 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 sitter 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 sitter for longer stays or first-time bookings. Read our tips for your first .
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Sleepy Hollow with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Sleepy Hollow. On Rover:
- 88% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 94% 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.
sitters 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 sitter.











