Dog Sitting Sleepy Hollow

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Over 90
pet parents in Sleepy Hollow have booked dog sitting

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Sitter Profile Image: Jacqueline & Uriel C.
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Jacqueline & Uriel C.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
180 reviews
54 repeat clients
6 years of experience
South Barrington, IL, 60010

Jackie & Uriel were incredible with Brick for drop in visits in the evenings while we were on vacation. They walked Brick each visit and he loved it! They kept us updated on literally everything! We got a report card with notes, photos, videos, potty details, treats given, etc. We would definitely hire them again!

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Melissa M.
Sitter Profile Image: Marilyn P.
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Marilyn P.
from
$20
per visit
5.0 out of 5 stars
37 reviews
11 repeat clients
40 years of experience
Elgin, IL, 60123

About: I love animals. I used to have three Shar Peis, which can be fairly temperamental, but I think I was their favorite walker. I've walked dogs with Wag for years and have cared for dogs ranging from tiny pups to large Anatolian Shepherds. I work from home most days, so having a dog or two in the house is not an issue. And, i don't mind sitting at other folks' homes, if the dogs are more comfortable in their own environment. I've recently fenced our backyard with a 6 foot privacy fence, so that visiting dogs will be secure during off-leash play. I live in a quiet neighborhood and there is a large park down the street, so walks can be quite lengthy, if the dog is up for it. I have a few chickens in a coop / run in the backyard. The app asks about my pets but then when I said ‘yes’ only allowed me to pick either ‘dog’ or ‘cat’ - and I couldn’t list birds so I couldn’t update it. 😕. Apparently Rover thinks there are only two kinds of animals??? Visits to the backyard are always supervised to keep everyone safe.

Sitter Profile Image: Myrlonette H.
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Myrlonette H.
from
$17
per visit
5.0 out of 5 stars
9 reviews
12 years of experience
Elgin, IL, 60123

About: Im a perfect fit to care for your dog .Because my schedule is flexible. I focus on positive reinforcement ensuring your dog feel safe with me . I currently working partime .some days im free to car for you pet..im available on weekends also. If you have errand I can watch your pet I have a fenced yard .neighborhood is great.your pet can run freely . Play catch with me theirs no kids just me and my husband

Sitter Profile Image: Alisa H.
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Alisa H.
from
$25
per visit
5.0 out of 5 stars
50 reviews
21 repeat clients
10 years of experience
West Dundee, IL, 60118

Alisa is great with Annie and Dexter. They were abused before we adopted them and sometimes have trust issues. They did not have any concerns with Alisa since the 1st meeting. We can see by the photos and videos Alisa sends us that they enjoy her visits

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Dawn M.
Sitter Profile Image: Danielle E.
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Danielle E.
from
$20
per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
23 years of experience
Gilberts, IL, 60136

About: I have taken care of animals for it seems like my whole life. I have experience administering medication both orally and through syringes and love to spoil dogs when walks and cuddles. I work for a school district so I my school day runs from 7:30-2:30, so no pet would be alone for long. I can do weekdays and weekends. I have experience going into someone’s home and watching their animals from there. I find it’s easier for on them when they are in their own home environment. I follow your routine and instructions and will let you know if I have any questions or anything comes up.

Sitter Profile Image: Toby J.
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Toby J.
from
$17
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
4 years of experience
Lake in the Hills, IL, 60156

Toby is always reliable and takes such good care of our pups. Highly recommend!

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Stacey H.
Sitter Profile Image: Stephanie K.
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Stephanie K.
from
$17
per visit
4.9 out of 5 stars
196 reviews
96 repeat clients
4 years of experience
SOUTH Elgin, IL, 60177

Stephanie is wonderful! She is very flexible. I needed her an extra day and she had no problem helping me out. She loves my little Luigi already and I'm sure he loves her because he behaves so well with her. So I'm told! I felt very comfortable when I met her. She brought her son with and Luigi took to both of them right away. My dog told me everything I needed to know about her right then and there. Thank you Stephanie and Rover. I feel at ease when I am away from home having Stephanie taking care if my boy! ❤

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Anna Marie C.
Sitter Profile Image: Amy F.
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Amy F.
from
$22
per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
15 years of experience
South Elgin, IL, 60177

We’re so grateful to Amy for taking such amazing care of our dog Max. She treated him with so much love and attention it truly felt like he was with family. Amy kept us updated, was super reliable, and went above and beyond to make sure Max was happy and comfortable. We came home to a very content pup and complete peace of mind. We highly recommend her to anyone looking for someone trustworthy and caring to look after their pets.

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Oz H.
Sitter Profile Image: Esther W.
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Esther W.
from
$18
per visit
1 year of experience
Streamwood, IL, 60107

About: I have about one year of hands-on pet ownership experience and have been around animals my entire life. I’ve helped train and care for dogs, including Collies and Hounds, with experience in basic obedience, leash walking, crate training, and puppy training. I enjoy walking dogs and providing enrichment to support their physical and mental well-being. I also love bathing dogs too! I have experience with a range of dog personalities, including puppies, senior dogs, and those with special needs, such as medication schedules or mobility considerations. I’m adaptable, patient, and willing to adjust my care style to fit each dog’s individual needs. I try and build my routine that balances and fits my dog and me! This includes daily walks, 10 minute sessions of training, playtime, and decompression time. I also give snuggle and cuddle time, but only if the dog I work with initiates. I also love giving my dog a well balanced diet and hydration especially in this hot weather. I also believe that a dogs world is as big as we allow, and so I love bringing dogs to new adventures, like hiking or a day at the beach. I try to include these at least weekly or bi-weekly. I also love having doggie play dates, and have some minor experience with dogs meeting for the first time! I currently live in an apartment, so I only service for home visits and walking right now. I’m familiar with fenced or semi fenced yards and crating. I have my own dog that I love taking out for walks and training, so if you don’t have a yard that isn’t an issue! I work great when I’m giving instructions in writing or verbal that best helps your doggie!

Sitter Profile Image: Erika G.
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Erika G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
255 reviews
65 repeat clients
30 years of experience
St. Charles, IL, 60175

Erika was super, she even went above and beyond and brushed my dog for me. Very thorough with what she did for me, which I appreciate as a first time user! Thank You Erika :)

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Ursula A.
Sitter Profile Image: nicole r.
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nicole r.
from
$22
per visit
5.0 out of 5 stars
10 reviews
5 repeat clients
West Dundee, IL, 60118

About: I have felt a calling towards dogs for quite some time now. I have a few dog friends, and feel a very deep, genuine, and pure connection with them. I hope that it's the same with your beloved furry friend, and I'm confident that it will be. Please allow me to respond to your booking request before sending your request to multiple parties.. This is appreciated! My schedule really is pretty packed right now, but mid-afternoons are pretty open most days.. I will take new clients if I am able to find a time slot for you, though! For now, I'd like to keep care either in your home, or outdoors. I will treat your home like it is my own. Thank you!

Sitter Profile Image: Grace K.
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Grace K.
from
$21
per visit
5 years of experience
West Dundee, IL, 60118

About: Been dog sitting for five years for daytime and overnight care. Available for walking, playtime, or just companionship for any size dog who needs some love 💗 I do currently have a part-time job Monday through Friday but am looking to walk dogs in the mornings and weekdays except on Wednesdays and can sit and do visits anytime on the weekends. I live in a very walkable and dog friendly area where your pets will always get the attention and time they need from me while also being safe and accepted.

Sitter Profile Image: Aaliyah C.
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Aaliyah C.
from
$15
per visit
11 years of experience
South Elgin, IL, 60177

About: I grew up taking care of my 2 collies and helping out with family members pets. I am experienced with managing large breeds and high energy dogs. I am currently on summer break from university, so I have a lot more free time. I am available on weekdays after 11 and weekends I have full availability. Safety is my top priority. I treat every pet as my own, maintaining a calm, clean, and safe environment. Ahead of time, I ask about any triggers your pet may have and make sure we walk in comfortable environments.

Sitter Profile Image: Meghan G.
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Meghan G.
from
$20
per visit
5.0 out of 5 stars
22 reviews
3 repeat clients
10 years of experience
Pingree Grove, IL, 60140

Meghan was great- I didn’t have to worry about our cat at all and trusted he was in good hands. She gave us great updates; will definitely book with her again!

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Chloe S.
Sitter Profile Image: Valerie P.
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Valerie P.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
119 reviews
46 repeat clients
13 years of experience
Elgin, IL, 60123

Great communication. I tried to contact 3 other providers and Valerie was the only one who responded. And she responded within an hour or two. Would definitely use her again.

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Christopher A.
Sitter Profile Image: Kierstin S.
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Kierstin S.
from
$17
per visit
11 years of experience
Elgin, IL, 60123

About: I’ve been a dog sitter since I was young. I’ve also cat sat for several family members before. I love working with cats, dogs, and any other creatures! I have a lot of experience administering almost any kind of medication, from administering fluids to oral meds to transdermal meds. No ask is too much for me! I work Monday-Friday eight to four. So I will work around that. I am also free all weekends. I will even do house stays if needed. I will treat your house as my own. I will leave it the way that you left it. I will also do anything that makes you feel more comfortable with me being in your house

Sitter Profile Image: Michael M.
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Michael M.
from
$35
per visit
4.9 out of 5 stars
24 reviews
8 repeat clients
10 years of experience
Algonquin, IL, 60102

About: I started and successfully managed my own dog walking business at the age of 15, serving clients throughout my local neighborhood. Over time, I built a loyal client base of more than 20 regular customers and provided a range of services, including dog walking, drop-in visits, and occasional bathing. This experience helped me develop strong time management skills, reliability, and a deep understanding of pet care. I currently have full availability and am eager to meet new dogs while continuing to provide dependable, high-quality care. As a welcome offer, new clients will receive $20 off their first booking with me. I am also happy to assist with basic dog training upon request, reinforcing positive behaviors during visits. While I do not have a yard available, I focus on providing attentive, active care through structured walks and drop-in visits to ensure each dog receives proper exercise, stimulation, and attention. In addition to dogs, I have hands-on experience caring for a wide variety of reptiles and exotic pets. I understand their unique environmental needs, including maintaining proper temperature gradients, humidity levels, and lighting. I have worked with species such as snakes, lizards, and other small exotics, ensuring their enclosures are clean, safe, and enriching. I am also knowledgeable about specialized diets, including live feeding, supplementation, and species-specific nutrition. I carefully monitor animal behavior and can recognize early signs of stress or illness. My approach emphasizes patience, consistency, and minimizing stress during handling and daily care routines. I am comfortable following detailed instructions and adapting to each pet’s individual personality and needs. Overall, I am committed to providing attentive, responsible, and knowledgeable care for all animals. I currently have unlimited availability and am here to meet all the new pups and help deliver exceptional service and dog training services if requested by owner. Upon arrival at a client’s home, if a backyard is available, I conduct a thorough perimeter check to ensure there are no gaps in the fence and that all gates are securely closed before allowing dogs outside. I follow each pet’s established feeding schedule and ensure fresh water is provided and replenished regularly. For overnight stays, I provide attentive in-home care to maintain your pet’s routine and comfort. If a walk requested during the booking exceeds 15 minutes an additional booking fee will apply for walks ranging from 30 to 60 minutes.  If your pet requires medication, please inform me in advance so I can ensure it is administered safely and according to your instructions.

Sitter Profile Image: Asher R.
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Asher R.
from
$15
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Elgin, IL, 60123

Asher was wonderful. He sent pictures and updates everyday of both cats, and our cats instantly loved him. Thank you!

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Monica G.
Sitter Profile Image: Danielle M.
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Danielle M.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
4 years of experience
West Dundee, IL, 60118

Perfect 10 !!! Danielle went out of her way for me. 100 % satisfaction! Received my report every walk and a picture of my dog. This was my first time leaving my dog without family, was nervous, but she put me at ease. Thank you again!! I highly recommend Danielle.

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Cindy M.
Sitter Profile Image: Nikitha R.
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Nikitha R.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
9 years of experience
West Park, Algonquin, IL, 60102

About: Hi there! I am so excited to finally be making my pet-sitting official with Rover. I am still new-ish to the area after having moved back in with my parents a little less than a year ago (originally from New Jersey, then moved to California for college and work). I have had the pleasure of taking care of my family dog (Winnie the Cavapoo) since we got her 9 years ago. Hanging out with her is one of my favorite things to do, and she truly makes each day better with every walk we go on and every cuddle we share. I've also gotten to dog-sit for some of my best friends and locals while I was in college, and it really helped me whenever I was missing my Winnie girl! My only hope is to provide you with peace of mind that your pup is in good hands with me! My schedule is pretty wide open and flexible! If there is a time/day on my schedule that looks unavailable, message me and I'll see if I can move things around to make it work (as I share a car with a family member). If you need me to come over and pet-sit at your home, I will respect all the rules you provide me with so you are comfortable with having me in your home while I watch your fur baby. Please let me know in advance to your booking if your pet is allowed on furniture, or in certain areas of your home, and what/where are absolute no-go's, so I can remember to keep them away from those areas. If you use a crate with them, please let me know how you use it with them - if they must be crated the entirety of time while indoors aside from meal and potty times, or if for certain periods of time. If you have a backyard that is fenced and secure, I am comfortable with letting them of their leash (if you permit it) so they have free reign to run around, but if it is not an enclosed space, I am not comfortable letting them off their leash, even if they are trained perfectly - just want to be safe and take all the precautions I can to make sure they are safe while with me!

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The median cost per visit for dog sitting in Sleepy Hollow is CA$20

Dog parents share their Rover experiences - Sleepy Hollow

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5.0 out of 5 stars

Madeline took care of our 4 german shepherds. They can be pretty energetic but she did a great job with them

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Ryan M.
Drop-In Visits
5.0 out of 5 stars

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

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Adam G.
Drop-In Visits
5.0 out of 5 stars

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

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Janos C.
Drop-In Visits
5.0 out of 5 stars

They took great care of Newton while I was on vacation! He loves them and I will definitely use their services again in the future! 10/10!!!!

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Diane S.
Drop-In Visits
5.0 out of 5 stars

Eloise was very responsive and helped us with a short notice request to visit our dogs. We appreciate her willingness to help and our dogs enjoy her. She’s responsible and dependable

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Janet H.
Drop-In Visits
5.0 out of 5 stars

We were thrilled with Karlie’s first drop-in visit today. Her kindness and attentiveness were truly remarkable. As soon as I stepped through the door, DixieBelle was bouncing up and down more than usual, and I’m certain she was expressing her immense joy and excitement about having a new friend. She can’t wait to see Karlie again.

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Victoria N.
Drop-In Visits
5.0 out of 5 stars

Madalynn did a wonderful job taking care of our dog while we were away. We will absolutely use her again!

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Joshua T.
Drop-In Visits
5.0 out of 5 stars

Jessica is great! She always shows at her scheduled times and takes great care of our pups. She’s goes above and beyond,

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Keith C.
Drop-In Visits
5.0 out of 5 stars

Abileah is super- fantastic. She took great care of my working line Mal. Please please please book !!!

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Tyler V.
Drop-In Visits
5.0 out of 5 stars

Peter was so wonderful to work with, friendly, great communication and fantastic helping take care of dogs! Will absolutely have Peter back again 🤗

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TIFFANY S.
Drop-In Visits
5.0 out of 5 stars

If you need someone to take care of your senior dog when you need to be away I highly recommend Derek. He is very reliable and sends detailed information about his visit as well as several photos. I will continue to use his services again in the future.

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Christine A.
Drop-In Visits
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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Sleepy Hollow average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Sleepy Hollow

Frequently asked questions about Rover

The average cost for Dog Sitting in Sleepy Hollow on Rover is $18.87 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting 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 Sitting. For more information on service fees, click here .

As of July 2026, there are 6,955 sitters on Rover offering Dog Sitting across Sleepy Hollow. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Sleepy Hollow stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 Rover's Trust & Safety page .

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.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters 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.

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:

  • 92% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 96% 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 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 sitter.

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