Dog Sitting Winnetka

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

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Over 8
pet parents in Winnetka have booked dog sitting

Winnetka, 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.

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Sitter Profile Image: jiayi x.
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jiayi x.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
19 reviews
5 repeat clients
10 years of experience
glenview, IL, 60025

Jiayi was incredibly professional, courteous, and worked so well with our dog! I would absolutely recommend her and will definitely try to book Jiayi again.

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Robert M.
Sitter Profile Image: Jon E.
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Jon E.
from
$30
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
27 years of experience
Wilmette, IL, 60091

About: I love animals. Growing up with pets of all kinds I learned to appreciate them and recognize their needs. I know the importance of bonding with them and find great joy in forming that bond. I did domestic care for four years and my primary job was tending to the animals. I am trustworthy and caring and I will put the needs of your pet first. Every time. I have made pet care my priority. I presently work full time in pet car. I also love pet photography and offer that as a service I am available on a drop-in basis and I can make myself available for overnights and extended stays as well. Whatever you need, don't hesitate to ask. I have cleared my schedule to make myself available to tend to dogs and cats full-time. I will walk your dog or simply hang out with your pet, whichever you need. I will build a trust with you, and your pet will know. I look forward to meeting you. I am very conscientious and responsible. I lost my own dog of 14 years and this has opened the door for me to be able to tend to your dog or cat. I can only offer the same loving care that I showed my own dog.

Sitter Profile Image: Addison A.
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Addison A.
from
$17
per visit
5.0 out of 5 stars
2 reviews
5 years of experience
Wilmette, IL, 60091

About: I’ve been living with and taking care of dogs since I could walk! In recent years, I have pet-sat for friends and family, and my family just got a new golden retriever puppy, in which I have been very involved with her training and care. I am quite open consistently this summer to take care of your pets! I spend my days working part-time and studying, leaving me with lots of time for drop-ins or house sitting. I am very attentive to pets, always looking out for signs of what they need or if they want to play. I love to give pets the enrichment they need to feel happy and loved!

Sitter Profile Image: Alyson W.
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Alyson W.
from
$20
per visit
5.0 out of 5 stars
6 reviews
18 years of experience
Evanston, IL, 60201

About: I'm attentive, detail-oriented, and generous with love and affection for all dogs I have the privilege to take care of. I have experience helping my family take care of our beloved dachshunds throughout my childhood (3 over the course of my life). I also have dog-sat for numerous families back when I lived in Minneapolis. I'm a dog lover through and through. I'm a busy grad student at Northwestern, so I can't have a dog of my own right now. Pet-sitting allows me to fulfill that desire for puppy cuddles when it fits my schedule! I have classes during the day and club activities at night, but lots of flexibility in my schedule to drive to pet sitting appointments. I would prefer to take care of dogs in their homes and go for walks in their neighborhood rather than stay in my small studio apartment. This makes the dog feel safe in their space. I am dedicated towards making dogs feel comfortable with me by following their existing routines and spending as much time as I can with them.

Sitter Profile Image: Rebeca A.
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Rebeca A.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
23 reviews
6 repeat clients
15 years of experience
Wilmette, IL, 60091

Absolutely recommend Rebeca! You can tell she really cares about dogs and loves what she does. My dog Snoopy has anxiety & is very shy at first but he felt at ease with her as soon as he met her during the meet and greet. She was so gentle, patient & sweet with him right away. I felt completely at ease knowing he was in such caring hands. I will def be booking with her again!

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Elaine D.
Sitter Profile Image: Parisa H.
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Parisa H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
116 reviews
31 repeat clients
10 years of experience
North Park, Chicago, IL, 60659

SO friendly, communicative, and patient. My pets are shy but she had no problem trying to gain their trust. I will absolutely be booking her again.

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Elisa D.
Sitter Profile Image: Kathleen K.
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Kathleen K.
from
$16
per visit
4.9 out of 5 stars
15 reviews
6 repeat clients
2 years of experience
Glenview, IL, 60025

About: My daughter and I have been boarding dogs for years and love it, we really focus on one families pet at a time so we give him/her our full love and attention. We will take up to 2 dogs at a time. We love to walk and play with the dogs. We have a large fully enclosed back yard in addition to a park at the end of our block we can walk dogs around a large walking path. We text photos and funny videos of us with your pet. My daughter is off to college this year and this will assist her school fund. We love these dogs as if they were our own. WE love taking care of pets, We love staying active walking and playing with the dogs. We will not take dogs if we do not have time for them. I have an enclosed back yard that is perfect for active dogs to chase birds and have a bit of an area to run free. We do walk the dogs to our local park at the end of our block.

Sitter Profile Image: Marissa H.
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Marissa H.
from
$12
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
20 years of experience
Evanston, IL, 60201

About: I ensure they receive the attention and provide expert supervision and ensure that every dog receives the highest level of and go beyond basic boarding by offering a variety of enrichment activities to keep your dog mentally and physically stimulated. From interactive toys and puzzles to group play sessions and nature walks, providing a range of activities to keep your dog happy and engaged. Clean and Safe Facilities: I follow strict cleanliness protocols to prevent the spread of illness and ensure a comfortable stay for every guest. Communication and Updates: I understand how important it is to stay connected with your pet while you're away… regular updates and photos so you can see how much fun your dog is having during their stay I am available all the time. I am very flexible and take my job and care seriously! Any medications or food allergies will be given priority. I have a fenced in yard with security for my surroundings and your pets. I also have a large crate as well and try to ensure safety first

Sitter Profile Image: jacqueline b.
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jacqueline b.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Highland Park, IL, 60035

About: I have had two beautiful golden Retrievers and love dogs in general. My golden Wyatt passed away but I adore and love and miss him so much. Now with a new year one year old puppy who is HUGE , I absolutely want to meet more friends of fur. I work daily but have a flexible schedule and can attend animals during the workday as I make my own hours. I also can stay overnight on Friday through Sunday for overnight sitting. I care for pets making sure they have the essentials, food and water. That being said I love to spend time with them all always they are amazing and I love playing with animals and making them feel as human as possible.

Sitter Profile Image: Natalia M.
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Natalia M.
from
$20
per visit
18 years of experience
Wilmette, IL, 60091

About: Growing up I have always had 3 cats at home and have pet sitted for a little over 5 years! My clients have had a mix of dogs and cats so I have experience with both! I can do drop-in visits in the mornings and evenings to feed them, walk them, etc. But the time frame can vary depending on the pets needs and my work schedule I feed them, play with them, walk them, and change the litter boxes (cats). If any more care is required you can text me if needed!

Sitter Profile Image: Riley K.
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Riley K.
from
$22
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
7 years of experience
Evanston, IL, 60201

About: I have been pet-sitting for 7 years; caring for animals is my passion! My style of sitting is treating every pet as if they’re my own😊🐾 I am currently working a part time job, so I may have certain windows of availability—but I am more than happy to work with you on times :) In my clients home, I will follow all rules and guidelines relating not only to their pet, but also to respecting their space as well.

Sitter Profile Image: Elizabeth T.
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Elizabeth T.
from
$20
per visit
2 years of experience
Glenview, IL, 60025

About: I've always loved caring for dogs and enjoy getting to know each pet's unique personality. I have experience caring for dogs of all sizes and ages, from tiny breeds and small dogs to large breeds, including pit bulls, as well as energetic puppies. Whether your dog loves long walks, playtime, cuddles on the couch, or simply sticking to their daily routine, I'm happy to provide the care they need. I've provided overnight house sitting for families, cared for pets in their own homes to help keep their routines consistent, and offered drop-in visits and dog walking. I'm comfortable handling dogs of all sizes, temperaments, and energy levels, and I understand that every dog has unique needs and deserves patient, individualized care. I know how important it is to trust the person caring for your pet, so I'll always treat your home with respect and your dog like they're part of my own family. I'll keep you updated with photos and messages while you're away, giving you peace of mind that your furry family member is safe, happy, and receiving plenty of love and attention I am a full-time kindergarten teacher, and caring for others is a big part of who I am. My job has taught me patience, responsibility, and the importance of creating a safe and loving environment — qualities I bring into caring for pets as well. Outside of school, I have time for early morning walks, check-ins, evening visits, and overnight stays. I truly enjoy spending my free time with animals and making sure they feel comfortable, happy, and cared for while their owners are away. I’m happy to follow each pet’s routine and give them the attention, exercise, and love they need. I treat every pet like they are my own and want them to feel safe, comfortable, and loved while their owners are away. I make sure to follow their normal routines, including feeding, walks, potty breaks, playtime, and any special instructions you provide. I have experience caring for dogs of all sizes, from puppies and small dogs to larger breeds, including pit bulls. I enjoy getting to know each dog’s personality and making sure they get the attention, exercise, and care they need. I’ll also keep you updated with pictures and messages so you can feel confident your pet is in good hands.

Sitter Profile Image: Matthew W.
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Matthew W.
from
$20
per visit
1 year of experience
Wilmette, IL, 60091

About: When I lived in the city (Lakeview), I frequently walked an energetic golden retriever, as well as played with her indoors, refilled her water, and rewarded her with treats. I have a very flexible schedule, as I am currently job hunting, writing music, and performing gigs on week and weekend nights, leaving a lot of time for dog walking and sitting. I make sure the pet I am taking care of is comfortable and has their needs for the day met (e.g., water filled, taken outside to go to the bathroom and play, and has toys readily available).

Sitter Profile Image: Rhea S.
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Rhea S.
from
$17
per visit
5.0 out of 5 stars
3 reviews
3 years of experience
Morton Grove, IL, 60053

About: I love all animals and treat them with the respect they deserve. Dogs are definitely my spirit animal. I really enjoy taking care of pets and playing with them! :) I am a summer camp counselor which leaves my nights and weekends free. I wouldn't want to spend my free time doing anything else. I love spending time with animals! :) I will be gentle with your pet and firm when necessary. I adore animals and treat every one with respect and care. I will make sure everything is clean and as it should be! :)

Sitter Profile Image: Evan P.
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Evan P.
from
$17
per visit
19 years of experience
Wilmette, IL, 60091

About: I’ve been around cats my entire life, so building trust and connecting with them comes naturally to me. I also gained experience dog sitting for neighbors when I was younger, which helped me develop a strong sense of responsibility and attentiveness when caring for pets. Today, I occasionally volunteer at Tails Together Animal Shelter, where my love for animals continues to grow. Whether it’s playtime, walks, or simply providing companionship, I’m committed to making pets feel safe, comfortable, and cared for while you’re away. My schedule is very flexible. I’m an honors student at Depaul on summer break. I’m available to work as early as 8 AM and as late as 10 PM. I have reliable transportation and have always taken being on time seriously. I’ll come to your home and follow any instructions you have for taking care of your babies! I’m organized and neat and understand that cleaning up after pets is part of the deal.

Sitter Profile Image: Chia Ping L.
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Chia Ping L.
from
$23
per visit
3 years of experience
Skokie, IL, 60077

About: I have a flexible schedule and can easily fit cat care into my daily routine. I’m available for drop-in visits and can provide feeding, fresh water, litter box cleaning, playtime, and companionship. I’ll follow your cat’s routine and send regular photo updates so you can have peace of mind while you’re away. Your cat’s safety and comfort are my top priorities. I’ll carefully follow all of your instructions, including feeding schedules, administering medications (if needed), and providing any special care your cat requires. I always make sure doors and windows are secure, keep the litter box clean, and provide a calm, stress-free environment. As a cat owner myself, I understand how important it is to earn your trust, and I’ll care for your cat as if they were my own. I’m currently a freelancer, which gives me a flexible schedule. I usually prefer afternoon visits because my meetings are typically finished by then, but I’m happy to accommodate morning visits too. I just ask for at least 3 days’ notice for morning bookings so I can plan my schedule accordingly. Your cat’s safety and comfort are my top priorities. During every visit, I’ll follow your care instructions carefully, including feeding schedules, fresh water, litter box cleaning, playtime, and administering medication if needed. I’ll make sure all doors and windows are secure before I leave and keep your home clean and tidy. As a cat owner myself, I understand that every cat has a unique personality, so I’ll respect their boundaries while making sure they feel safe, comfortable, and well cared for. I’ll also send regular photo updates so you can have peace of mind while you’re away.

Sitter Profile Image: Coty C.
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Coty C.
from
$35
per visit
5.0 out of 5 stars
66 reviews
22 repeat clients
20 years of experience
Evanston, IL, 60201

Cody is amazing! She took the time to learn my dog’s specific needs and personality, and tailors her interaction with them. Her many years of experience with dogs was evident in the way that she cared for my senior dog’s needs and quirks. Aside from her professionalism (always on time, dependable, reliable, trustworthy), she is passionate about dogs, and my little one absolutely loved her! She went out of her way to make sure that my dog felt safe and happy while I was away, and sent me lots of cute pics. I can’t say enough great things about her. You will love her. I will definitely be rebooking her again!

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Nancy V.
Sitter Profile Image: Natalie C.
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Natalie C.
from
$30
per visit
5.0 out of 5 stars
36 reviews
15 repeat clients
11 years of experience
Skokie, IL, 60077

Natalie took care of our dog Sophie over a long weekend. She did an excellent job! The dog had recent surgery and had some activity restrictions which Natalie followed very closely. She sent us texts, pictures and comments with each visit! This helped us to know that the dog is very well taken care of and the pictures showed us how happy she is. Natalie spent time and pet the dog with each visit. Upon our return we found a happy, and healthy dog. We are planning to use Natalie’s services again. We highly recommend Natalie! Thank you Natalie!

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Ganka M.
Sitter Profile Image: Yao Q.
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Yao Q.
from
$17
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
4 years of experience
Morton Grove, IL, 60053

About: I’ve had a passion for animals since I was a little girl. I get along with all my neighbors’ dogs and my neighbors rely on me to take care of them some times. My old roommate has a golden retriever and I love taking care of him, giving him a bath and walking him. I have two cats at home and I even taught them some tricks! I’m currently working part time only on Mondays and Thursdays. So I have lots of free time outside of work taking care of your dogs and playing with them! I also have a car so I can drive to wherever you are and take your dogs for a walk where they are the most comfortable with. I live right next to the bike trail and woods, which is a paradise for dogs! If you have an athletic or active dog, I’ll take your dog running the trails, swimming in the pond, and have all the fun in the outside world! If your dog is less active, I’ll give your dog all the comfort and love at home, making sure they are well fed and entertained.

Sitter Profile Image: Jenny D.
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Jenny D.
from
$20
per visit
5.0 out of 5 stars
1 review
6 years of experience
Wilmette, IL, 60091

About: Active in the outdoors, and attentive to dogs' behaviors, I'm a caring listener who will make sure your dog has a great time! As a dog owner, I've been through training with the Humane Society for Dog Manors 1 & 2. I understand dog body language communication, and know its important to listen to what your dog is saying! Whether they are fearful, playful, bored, sad or joyful - I'll make sure they are taken care of with love and understanding. I"m all about paws-ative reinforcement! I love to run and play outside whenever possible. I would love to take your pup to the beach, park, or just around the block for some fresh air! I'll make sure to send you plenty of pics to make you feel part of the pack! I've had the comfort of experiencing life with dogs throughout my life and I appreciate how much joy they bring to our lives. I'll always make sure to bring a bit of fun to their day as well :-)

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The median cost per visit for dog sitting in Winnetka is $20

Dog parents share their Rover experiences - Winnetka

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5.0 out of 5 stars

Jiayi was incredibly professional, courteous, and worked so well with our dog! I would absolutely recommend her and will definitely try to book Jiayi again.

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

Melisa always goes the extra mile. She cared for our two elderly Chihuahuas for a long weekend. Handled meds, feedings and cleanup like a star.

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

The best pet sitter. Rosy literally just saved my cat’s life, when she noticed he was not his usual self, took him to the vet, where they identified he had a urinary blockage and likely just hours to live. How lucky for us that Rosy was caring for our animals and so observant. Thank you, forever. 🌟🌟🌟🌟🌟

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

Absolutely recommend Rebeca! You can tell she really cares about dogs and loves what she does. My dog Snoopy has anxiety & is very shy at first but he felt at ease with her as soon as he met her during the meet and greet. She was so gentle, patient & sweet with him right away. I felt completely at ease knowing he was in such caring hands. I will def be booking with her again!

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Elaine D.
Drop-In Visits
5.0 out of 5 stars

Donna was wonderful! She texted pictures and updates every time she was here. Henry really liked her, and he was well taken care of. It gave me peace of mind knowing that he was happy. I would hire Donna again any time.

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Marjorie A.
Drop-In Visits
4.0 out of 5 stars

There was one missed visit out of 5. Taylor was apologetic & took care of the dogs as scheduled for the rest of the visits.

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Marilee E.
Drop-In Visits
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Sitters in Winnetka average 7
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FAQs for Drop-In Visits - Winnetka

Frequently asked questions about Rover

The average cost for Dog Sitting in Winnetka on Rover is $21.09 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 11,678 sitters on Rover offering Dog Sitting across Winnetka. 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 Winnetka 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 Winnetka 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 Winnetka 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 Winnetka. On Rover:

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

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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