Dog Sitting Westchester

Book a Westchester dog sitter to watch your dog in your sitter’s home or yours.

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Over 38
pet parents in Westchester have booked dog sitting

Westchester, 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.

1 / 1
Sitter Profile Image: Heather O.
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Heather O.
from
$25
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
40 years of experience
Forest Park, IL, 60130

Thank you for the last minute help!

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Kim J.
Sitter Profile Image: Marin H.
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Marin H.
from
$22
per visit
5.0 out of 5 stars
10 reviews
1 repeat client
14 years of experience
Oak Park, IL, 60302

Marin was awesome. She communicated well and took great care of our dog.

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Nikhil P.
Sitter Profile Image: Dana R.
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Dana R.
from
$29
per visit
5.0 out of 5 stars
12 reviews
1 repeat client
25 years of experience
La Grange, IL, 60525

Dana given a most unusual assignment jumped right in!

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Linda R.
Sitter Profile Image: Estefani C.
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Estefani C.
from
$15
per visit
6 years of experience
Melrose park, IL, 60160

About: Hi my names estefani! I’ve loved all animals since i was baby and have grown up around them! Would love to meet all of ur furry friends in ur families any shape or size! i am reliable and very responsible and will keep ur fur baby safe and treat it as if it were my own! (meaning lots of love and loads of belly rubs) i do consistent updates and will be your very own furry friends photographer 📸🐶 Ademas soy bilingüe y hablo español! I am a student in high school who gets out at 3 but i’m usually all ready to go by 4 to start taking care of every and all types of fur babies! I have loads of free time afterschool and during weekends since i’m primarily focusing on school right now and doing rover 😊 i will ensure your furry friends are protected and safe since i know just how important they are to ur families and how much we all worry about leaving our babies with ones we trust!

Sitter Profile Image: Tamara C.
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Tamara C.
from
$25
per visit
5.0 out of 5 stars
104 reviews
26 repeat clients
17 years of experience
Brookfield, IL, 60513

Tamara dropped in to check on our dog while we were out of town for a week. She came to our home twice a day and sometimes 3 to check on our dog. She was amazing and we felt our pet was well cared for while we were gone. Tamara sent us pictures and videos at every visit. We could tell how much she cared for our dog. I highly recommend her and would not hesitate to hire her again.

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Nora C.
Sitter Profile Image: Grace M.
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Grace M.
from
$20
per visit
5.0 out of 5 stars
221 reviews
77 repeat clients
6 years of experience
Riverside, IL, 60546

Grace was the best! She sent detailed information to me with every visit and pictures. She even went as far as to take the scooped cat litter out with her when she left. I will definitely be using her again in the future!

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Tara K.
Sitter Profile Image: Justice P.
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Justice P.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
46 reviews
20 repeat clients
1 year of experience
Austin, Chicago, IL, 60644

Justice is great! She is reliable, friendly, and sent thorough updates and pictures while checking in on Cooper. Everything went super smoothly and we'd be happy to work with her again!

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Michael M.
Sitter Profile Image: Nastassia G.
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Nastassia G.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
71 reviews
20 repeat clients
35 years of experience
La Grange, IL, 60525

Nastassia did a great job by hanging out with the kitties and providing medication to our senior cat on a specific schedule. The cats were doing great when we came back and I would use her services again!

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Etienne S.
Sitter Profile Image: Sarah P.
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Sarah P.
from
$25
per visit
5.0 out of 5 stars
44 reviews
8 repeat clients
12 years of experience
Western Springs, IL, 60558

Sarah is so kind and caring with our energetic puppy! She creates a nurturing and playful environment to keep him busy while we're gone. I highly recommend her!

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Gabrielle S.
Sitter Profile Image: Stephanie M.
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Stephanie M.
Star Sitter
from
$35
per visit
4.9 out of 5 stars
42 reviews
13 repeat clients
10 years of experience
Irving Park, La Grange, IL, 60525

After having to have an emergency scheduling Stephanie was absolutely fantastic, she was quick to reply, communicative, respectful and very kind. She gave us constant updates on our cat Freyja along with photos. We would happily use her services again.

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Joseph J.
Sitter Profile Image: Natalia B.
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Natalia B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
80 reviews
13 repeat clients
15 years of experience
Berwyn, IL, 60402

Natalia was great with Flynn. He can be a little scaredy cat/hisses at strangers but he really warmed up to her. She was great at communication and pics/videos and put my mind at ease. Will def use her again in the future.

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Jessica M.
Sitter Profile Image: Tea Agne J.
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Tea Agne J.
from
$30
per visit
5.0 out of 5 stars
15 reviews
6 repeat clients
18 years of experience
Forest Park, IL, 60130

About: Having lived with, and cared for dogs for much of my life, you can expect that your pet will receive my full attention and devotion during the time that we work together—not just their basic health, safety and food/outdoor needs, but also the affection that keeps them feeling loved. I currently work from home-where we have a large backyard with endless fascinating smells—and I rarely leave client dogs unattended. My own Boston Terrier, Hutson, currently 8 years old, is a well socialized, solid companion who is very good with canine communication, and will give space to dogs who need and request it, or play with those who share his play style (I monitor very closely). He’s especially good with puppies. I am also very comfortable maintaining obedience protocols when needed, but also flexible and realistic about dogs' behavior. I have some experience with dogs' health needs. I have helped care for my mother's cocker spaniel, whose serious autoimmune condition has required the administration of daily oral medication, including immune system blockers and steroids. I've also cared for a four month-old Boston Terrier puppy who when we first met needed medication administered twice daily. Outside my interest in animals, I've run a summer program for high school students, and have significant and transferable experience handling emergency situations and working under pressure. I currently work from home, and I rarely leave client dogs unattended. We have a large backyard full of interesting smells and occasional visits from other animal friends, from squirrels to rabbits and opossums. I also love longer walks through nearby forest preserved if dogs are well suited to this. Having lived with, and cared for dogs for much of my life, you can expect that your pet will receive my full attention and devotion during the time that we work together—not just their basic health, safety and food/outdoor needs, but also the affection that keeps them feeling loved. I'm an advocate of positive training techniques, and try to provide mental stimulation. My own Boston Terrier, Hutson, currently six years old, is a well socialized, solid companion who is very good with canine communication, and will give space to dogs who need and request it, or play with those who share his play style (I monitor very closely).

Sitter Profile Image: Jessica C.
Verified Enhanced Background Check
Jessica C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
309 reviews
71 repeat clients
20 years of experience
Riverside, IL, 60546

Jessica did a great job at communicating with us. She sent daily pictures of her time with our pet. She is very dependable. Will be using her services again.

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Loretta W.
Sitter Profile Image: Angelina O.
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Angelina O.
from
$22
per visit
5.0 out of 5 stars
92 reviews
46 repeat clients
15 years of experience
Brookfield, IL, 60513

Angelina was wonderful! She took great care of our elderly cat and had helpful suggestions for some of his ailments. We will definitely have her back again the next time we are traveling.

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Shawn K.
Sitter Profile Image: Collette W.
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Collette W.
from
$21
per visit
5.0 out of 5 stars
99 reviews
19 repeat clients
20 years of experience
Villa Park, IL, 60181

Collette is the most kind, caring, attentive, responsible sitter! Both of our cats loved her. She is incredibly patient and our shy & overly cautious kitty even loved her. :) We will be booking her again!

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Bethany K.
Sitter Profile Image: Kate B.
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Kate B.
from
$20
per visit
5.0 out of 5 stars
17 reviews
8 repeat clients
6 years of experience
Brookfield, IL, 60513

Amazing!! So kind and great with our dogs. Excellent communication and so grateful she could accommodate extra visits last minute. Will definitely book her again!!

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Lisa K.
Sitter Profile Image: Jhadira V.
Verified Enhanced Background Check
Jhadira V.
from
$22
per visit
1 repeat client
7 years of experience
Countryside, IL, 60525

About: Hi, I’m Jhadira! 👋 I recently experienced a layoff from my corporate HR career, so I’m taking this opportunity to spend my time doing something I truly love, caring for dogs! I’m located in the La Grange area and have a large, fully fenced backyard that’s perfect for safe, supervised playtime. I share my home with my two spoiled pups, Charlie and August, and I also help care for my family’s senior dog, Tony. Caring for dogs through every stage of life has taught me that each one has their own personality, routine, and unique needs. I have over 7 years of hands-on experience caring for dogs of all ages, breeds, and temperaments. My experience includes potty training puppies, working with high-maintenance dogs, caring for puppies undergoing treatment for intestinal worms and other temporary medical needs, administering oral medications, basic obedience training for both puppies and older dogs, walking and running with active dogs, and providing extra patience and specialized care for senior dogs. Whether your dog is full of energy, needs a little extra attention, or enjoys a slower pace, I’m happy to tailor my care to what makes them feel most comfortable. I’m also training for a half-marathon myself so if your dog needs that outdoor exercise I would gladly love the company on my runs! As a dog mom myself, I know how much trust it takes to leave your furry family member with someone else. That’s why I treat every dog as if they were my own. Their safety, happiness, and well-being are always my highest priorities. I’ll follow your dog’s routine closely, provide regular photo and video updates, and make sure they receive plenty of love, attention, exercise, and enrichment while you’re away. Over the years, I’ve also built relationships with wonderful local pet professionals. If you ever need recommendations, I’m happy to share trusted groomers and veterinarians that I’ve had great experiences with. Whether your pup loves long walks, backyard zoomies, playing fetch, learning new tricks, or curling up for a nap, I’ll make sure they feel safe, loved, and right at home. I can’t wait to meet you and your best friend! Open schedule, I have my own two dogs I look after but have all day to drop in for a walk or to check in on yours! I have a tight schedule with my own dogs and will make sure to make your fur baby feel as safe and loved as if they were home.

Sitter Profile Image: Lorraine C.
Verified Background Check
Lorraine C.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
105 reviews
30 repeat clients
25 years of experience
Westchester, IL, 60154

Lorraine was wonderful! Very easy to communicate with & did great with my dogs!!!!

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Paula K.
Sitter Profile Image: Rafael L.
Verified Enhanced Background Check
Rafael L.
from
$20
per visit
10 years of experience
Maywood, IL, 60153

About: I have experience taking care of pets for more than 10 years I have always had animals and I teach them where to do their needs and tricks to improve their performance and well-being I have all the time available to take care of pets since I work with delivery applications so I manage my time Full time for animal I only have one cat in my house I can take it for a walk I have a park nearby and I have a backyard to take them out to do their needs

Sitter Profile Image: Dezmond M.
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Dezmond M.
from
$24
per visit
5.0 out of 5 stars
40 reviews
16 repeat clients
8 years of experience
Hinsdale, IL, 60521

Dezmond was extremely helpful for a last minute drop-in. He was able to administer my dog's insulin shot with ease. Benji appreciates you and thank you again!

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Allison C.
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The median cost per visit for dog sitting in Westchester is $20

Dog parents share their Rover experiences - Westchester

1 / 1
5.0 out of 5 stars

I truly appreciate Esther. She makes sure Ace gets some loving! Ace appreciates his play time with her

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Kareline L.
Drop-In Visits
5.0 out of 5 stars

An incredible sitter overall! Checked in consistently and helped my anxious dog feel safe and comfortable even with stormy weather. She was very patient with my shy and nervous dog, sent tons of photos and updates, and went above and beyond to play with and comfort Addy. Would 100% re-book her services and recommend her to anyone looking for trustworthy and consistent care for their dog!

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

Isabella was wonderful with my dog while I was gone for the weekend! He's older and picky and needs a little extra care...she was great with drop in visits, giving him extra attention, and making sure he got enough exercise while I was away. Very kind and reliable, will definitely book with Isabella again!

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Sarah L.
Drop-In Visits
5.0 out of 5 stars

Great job. Thank you for the photos. And the little live update on the camera. Jake seems very happy with you.

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Becky P.
Drop-In Visits
5.0 out of 5 stars

We booked with Estefanía for her to visit our dog three times a day during our week-long trip. She was always super professional- quick responses when I texted her any last-minute requests or instructions. She also brought in our trash bins and kept our plants alive:) Bruno was happy when we got home, but definitely no stress when we were away!

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Kristen B.
Drop-In Visits
5.0 out of 5 stars

Lexi is amazing! I was fortunate to find her in a last-minute situation, and she enthusiastically took on three drop-in visits with less than 24 hours’ notice. My timid rescue beagle warmed up to her immediately, she followed very specific instructions perfectly, and I will definitely be using her services again!

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Nicole B.
Drop-In Visits
5.0 out of 5 stars

Paulina was amazing with my dog Turbo! She treated him like her own and was patient with him and his needs especially with him being a puppy. I would recommend her to anyone and will continue to keep on rebooking her whenever I need to!

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

Always a pleasure having Brittany watching my critters. My dog and kitty love her, and she does everything I want and more. Thanks again

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Sandra B.
Drop-In Visits
5.0 out of 5 stars

Tamara dropped in to check on our dog while we were out of town for a week. She came to our home twice a day and sometimes 3 to check on our dog. She was amazing and we felt our pet was well cared for while we were gone. Tamara sent us pictures and videos at every visit. We could tell how much she cared for our dog. I highly recommend her and would not hesitate to hire her again.

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

Angelina is a caring and dependable caregiver for our beloved dog, Walter. She not only takes him out but spends time with giving him attention and relaxing belly rubs and pets. He is clearly happy to see her when she arrives.

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Phillip L.
Drop-In Visits
5.0 out of 5 stars

Our pup had 2 walks with Nastassia and both were great. Appreciated all the communication before & after. This was my first experience with Rover.

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

Kristen has been amazing! She is kind and patient, and has been very reliable. She has been great at taking care of my little Yorkie, taking her for walks and playing with her to burn off some energy! Highly recommend!

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Beth F.
Drop-In Visits
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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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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

Meet local sitters who will treat your dogs like family

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Sitters in Westchester average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Westchester

Frequently asked questions about Rover

The average cost for Dog Sitting in Westchester on Rover is $27.75 per visit (as of September 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 September 2026, there are 12,363 sitters on Rover offering Dog Sitting across Westchester. 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 Westchester 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 Westchester 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 Westchester 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 Westchester. On Rover:

  • 91% of sitters can help with special care needs
  • 95% 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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