Pet Sitting Windsor

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Over 191
pet parents in Windsor have booked pet sitting

Windsor, Find top rated pet 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: Taryn E.
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Taryn E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 36 reviews
17 repeat clients
4 years of experience
Windsor, WI, 53598

“Taryn was kind and very patient with my older, unsure little dog. Everyday Taryn took her time to get to know him. She was friendly and gentle allowing him to get used to her visits.”

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ZOE M.
Sitter Profile Image: Tricia D.
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Tricia D.
from
$15
per visit
5.0 out of 5 stars
• 1 review
2 repeat clients
14 years of experience
DeForest, WI, 53532

About: Experienced & Loving Dog Care | 14+ Years in Rescue, Training & Medical Care Dogs have always been at the heart of my life—growing up, they were truly cherished members of our family, and that philosophy guides how I care for them today. For over 14 years, I have worked hands-on in rescue shelter environments, giving me deep experience with dogs of every size, age, and background—from tiny toy breeds to gentle giants. My time in rescue has taught me patience, intuition, and deep compassion. I’ve had the privilege of working closely with extremely fearful dogs, including those rescued from puppy mills who had never known human touch or seen the light of day. Helping them learn to trust, feel safe, and discover the joy of just being a dog is one of the most rewarding parts of my work. What I Bring to Your Dog’s Care: Specialized & Behavioral Care: Experienced in basic dog training and working with a wide range of unique personalities (from energetic pups to timid rescues). Medical & Recovery Support: Proficient in administering oral medications (pills and liquids) and supporting dogs through physical therapy and post-op recovery. Family-Level Love: Every dog in my care is treated with the exact same warmth, attention, and affection I give my own. Dependable & Adaptable: I have a flexible schedule, pay close attention to detail, and follow your home and care instructions to the letter. (I also have experience in caring for small mammals and reptiles!) I’d love to meet your pup and provide them with a safe, comforting, and fun environment while you're away! Pet care isn’t just something I squeeze into my schedule; it’s central to my day to day life. With a flexible schedule, I am able to dedicate focused, quality time to the animals in my care without rushing. Whether your pet needs a mid-day walk, precise medication timing, or dedicated cuddle and play sessions, my routine naturally accommodates their specific needs. I prioritize consistency so your pet’s daily rhythms—feeding times, exercise, and rest—remain uninterrupted while you’re away. Safety and trust are the foundation of everything I do. Having spent over 14 years working in animal rescue, I am trained to maintain a secure, low-stress environment and anticipate potential hazards before they happen. In Your Home: I strictly honor your pet’s safe space and established routines. I keep doors and gates secure, ensure all foods and medications are safely stored, and strictly follow your home rules. Building Trust: I let pets approach me at their own comfort level, using positive reinforcement, soft body language, and patience—especially with anxious or rescue pets. Health & Safety: I am highly experienced in monitoring health cues, managing medical recoveries, and administering medications, giving you complete peace of mind that your pet and home are in capable, loving hands.

Sitter Profile Image: Mira D.
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Mira D.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 10 reviews
3 repeat clients
10 years of experience
Waunakee, WI, 53597

“Mira was great! She was very pleasant, quick to communicate, and scheduled a meet & greet shortly after accepting the booking. She took care of my kitty with drop-in visits over three days and sent me updates and pictures every day, which I really appreciated. It was obvious that she genuinely cared about my cat and made sure she was well taken care of. She also arrived within the scheduled time each day. I’ll definitely be booking Mira again! 🐾❤️”

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Jennifer B.
Sitter Profile Image: Tiana B.
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Tiana B.
from
$20
per visit
5.0 out of 5 stars
• 32 reviews
13 repeat clients
5 years of experience
DeForest, WI, 53532

“Tiana was great! She was timely, communicated well, and was great to work with. She came and let out my dog while I was working and took great care of him!”

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Daria D.
Sitter Profile Image: Hailey M.
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Hailey M.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
• 46 reviews
11 repeat clients
10 years of experience
Madison, WI, 53704

“Hailey was amazing! She was super responsive and agreed to watch my dog last minute over Labor Day Weekend and was a lifesaver. She sent plenty of pics and let me know how Delilah was doing and what they got up to on her visits. I will absolutely be reaching out again in the future!”

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Emma B.
Sitter Profile Image: Rachel J.
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Rachel J.
from
$15
per visit
17 years of experience
Cherokee Park, Madison, WI, 53704

About: I grew up in a household with a minimum of us having 3 dogs at a time, ranging from 4 lb to 150 lb (shorkie/ irish wolfhound)! I'm a travel nurse in the area, and can't travel with pets, looking to spend some of my free time loving on animals. Along with having dogs growing up, we typically always had a cat or 2 to snuggle up with! I currently work 3 12 hours shifts in a week at the hospital. I do mostly night shift, however some day shifts. I typically have 4 days a week that I can spend watching your furry loved one! Since I am here on a travel nurse assignment, I am unable to watch your pet in my airbnb rental. This profile is for drop ins/ walking :)

Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 54 reviews
22 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

“Liz was very flexible and willing to help with my 3 pit bull/bully doggies on short notice. Very kind and understanding. Great help. Thanks Liz!”

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Julia X.
Sitter Profile Image: Phillip C.
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Phillip C.
from
$20
per visit
5.0 out of 5 stars
• 8 reviews
2 repeat clients
20 years of experience
Sun Prairie, WI, 53590

About: I’m experienced with both cats and dogs, house sitting and plant sitting if needed. I have a senior cat myself and two other younger cats but I also grew up around dogs and love to dog sit and take dogs on walks when the weather permits. My schedule is usually very flexible. I’m a full time student and I’m working part time from home in the Miami area. As long as I have a solid Wi-Fi or data connection for a hotspot I’m good to go. If there isn’t already explicit instructions my usual schedule would be to walk the dogs every 2-4 hours (puppies more than that till their potty trained) and feed the animals as instructed. Cats and dogs both need their daily playtime as well. I’m willing to spend the night if you’d prefer or just come and spend the workday with them 12+ hours a day.

Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 71 reviews
18 repeat clients
20 years of experience
Madison, WI, 53718

“Jackie was a perfect fit for my drop in visits and day care. She was thorough in getting to know Apollo and his needs. She followed my recommendations and went above and beyond to make sure Apollo was taken care of, some people are just naturals when it comes to caring for pets, and I believe Jackie is one of them, 100/10 recommend!”

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Megan B.
Sitter Profile Image: Lindsey D.
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Lindsey D.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
• 53 reviews
22 repeat clients
15 years of experience
Sun Prairie, WI, 53590

“Love how fast she is to respond and always has positive things to say about our pups who can be a little crazy 🤪 We trust her with their care.”

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Samantha T.
Sitter Profile Image: Mary W.
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Mary W.
from
$14
per visit
5.0 out of 5 stars
• 11 reviews
5 repeat clients
20 years of experience
High Crossing, Madison, WI, 53718

“Mary was communicative, asked questions, and gave excellent care for my dog. Thanks Mary! Will definitely book again.”

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Krista I.
Sitter Profile Image: Anna M.
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Anna M.
from
$13
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
15 years of experience
Madison, WI, 53704

About: I grew up with dogs and miss having them in my life dearly! I have experience, walking, feeding and bathing dogs. I have experience with them all — from tiny schnauzers to giant goldendoodles that pull you along — and I would love to meet your furry friend! I have a full-time job so I’m available in the evenings and weekends for dog walking and visits. I could potentially take a calm doggo to work with me for pet sitting during the day, and I could also do early morning walks or visits when needed! When not in a fenced-in yard or dog park, I keep dogs on a leash to keep them safe. I can also adapt to your practices such as putting the dog in a harness, getting them into a crate, or closing certain doors when needed.

Sitter Profile Image: Jamie Z.
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Jamie Z.
from
$25
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
2 years of experience
Waunakee, WI, 53597

About: I’ve grown up with dogs my entire life and currently have three dogs of my own, all with very different personalities and needs. I’ve put a lot of time into training and creating a successful multidog household, which has given me experience with everything from basic obedience and leash manners to reactivity, resource guarding and special-needs dogs. I’m comfortable following established routines, using the training methods and equipment your dog is accustomed to, and adjusting my approach based on each individual dog. I understand that not every dog is a social butterfly, and I’m happy to give dogs the space, patience and structure they need to feel comfortable. Most importantly, I know how nerve-wracking it can be to trust someone else with your dog. I’ll care for yours with the same attention and respect I expect for my own. As a registered nurse, I’m dependable, detail-oriented and comfortable following specific care and medication instructions. I am not only certified in human CPR but also Red Cross Dog/Cat/Pet CPR and first aide certified. I’m also used to communicating clearly, so you can expect plenty of updates while your dog is in my care I’m an RN with a rotating schedule, which gives me several days off during the week and plenty of flexibility to care for your pets. On my days off, I’m available for walks, drop-in visits, playtime and plenty of attention! I am home most of the time and my husband works from home so someone will usually be here. With the occasional instances of going out a few hours at a time. We do keep our dogs crated while we are gone and have cameras on the kennel/dog room to keep an eye on them. I know every dog has their own routine, personality and comfort level. I’m happy to follow your established routine and any specific instructions for feeding, walks, medications, crates or training. I have experience with multidog households, reactive dogs and special-needs dogs, so I’m comfortable adjusting my approach to what makes your dog feel safest and most comfortable. I’ll also keep you updated with photos and messages so you can feel confident your pet is well cared for while you’re away

Sitter Profile Image: Jordan F.
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Jordan F.
from
$20
per visit
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
DeForest, WI, 53532

About: Hello! My family and I currently have a beautiful silver Laborador Retriever, Mae, who brings so much happiness and energy to our lives. I’m a firm believer that a house is not a home without a furry friend! I have a pretty flexible schedule during the day, and would love to help out some pet owners in need of anything from short potty break, midday play, or walk while you’re out! I’ve grown up with dogs my entire life and am super comfortable with pets of all ages and sizes and have a lot of experience, including caring for older pups who might need a little extra TLC. I also have experience caring for cats (including those who have medication needs). Looking forward to hearing more of your pet care needs and meeting some new furry friends!

Sitter Profile Image: Kylie U.
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Kylie U.
from
$20
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
10 years of experience
Westchester Gardens, Madison, WI, 53704

“Kylie was absolutely wonderful with our cats, Georgie and Weezy!! She was punctual, attentive, and kept us updated with photos and messages during her drop-in visits. Georgie really liked her and she tends to be more timid with strangers. We’ll definitely book with Kylie again!”

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Jody & Nick J.
Sitter Profile Image: Hailey R.
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Hailey R.
from
$13
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
9 years of experience
Sun Prairie, WI, 53590

“Hailey was very responsible and communicative. Would definitely have her help with Boots again!”

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Michelle R.
Sitter Profile Image: Tara S.
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Tara S.
from
$13
per visit
18 years of experience
Madison, WI, 53718

About: I grew up on a farm and so I handled a wide variety of animals. I’m in nursing school and want a side hustle that I will enjoy doing. I can walk dogs Monday - Friday from 5:30 on. I have my own 2 Fur babies at home. One being a 2 year old boxer and the the other being a 3 year old mix. I know a lot about animals because I grew up with them. I have worked with a vet in Wisconsin a bit too so I know how to look for signs of sickness.

Sitter Profile Image: Lynne O.
Verified Enhanced Background Check
Lynne O.
from
$20
per visit
5.0 out of 5 stars
• 11 reviews
1 repeat client
30 years of experience
Fitchburg, WI, 53711

“We had a wonderful experience with Lynne! She was reliable, caring, and kept us updated while we were away. It was clear our pups were happy and well cared for, which gave us great peace of mind. We would definitely recommend her and would happily book with her again!”

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trina m.
Sitter Profile Image: Cassie A.
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Cassie A.
from
$21
per visit
4.9 out of 5 stars
• 53 reviews
15 repeat clients
10 years of experience
Sun Prairie, WI, 53590

“Cassie took excellent care of our kitties while we were in Florida and even brought in our mail and packages for us! I would highly recommend her for your petsitting needs.”

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Tina V.
Sitter Profile Image: Brandi V.
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Brandi V.
from
$20
per visit
8 years of experience
Windsor, WI, 53598

About: I’ve been dog sitting for a couple years now. I’ve had experience from little to big dogs. From a basenji, labrador, german shepherd, great pyrenees mix, a yorkie, and a few other breeds! Friends rely on me to exercise, feed, and give attention to their fur baby. 😊 I have plenty of time on the weekends! I’m currently available at any time Friday-Sunday to take care of your sweet pets! Can start at any point of the day or night! I take care of pets as if they were my own! 🥰 I care about their safety, what they eat, who comes around them, how much outside time they get. I promise to take care of them and give them all the attention. I want to be able to give them some love and snuggles while watching some tv. I make sure to stick to their food schedule and like to let them out every 2-4 hours. Daily exercise is important to me, I like to go on walks and can always use a walking buddy! 🐶

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The median cost per visit for pet sitting in Windsor is $20

Pet parents share their Rover experiences - Windsor

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5.0 out of 5 stars

Heather did an exceptional job caring for our very active golden retriever. She is timely and loving! 💕

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

Taryn is simply the best! I highly recommend her and will use her for all of my future sittings. She took care of my fur babies like they were her own and went above and beyond; I can’t thank her enough for her thoroughness and quality of care. Book her! You won’t regret it.

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Mandy W.
Drop-In Visits
5.0 out of 5 stars

We had daily drop in visits with my dog and she was always there on time and gave Odin such great care. I would absolutely use her services again.

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

Kelsey was great with our dog and his drop-in visits! I appreciated her flexibility with my visit time changes and her communication was awesome. I loved the pictures she included in her updates! Would definitely book her again

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Kristina J.
Drop-In Visits
5.0 out of 5 stars

Brandy is fantastic. We've worked with her multiple times, and she is always a accommodating and a great communicator. She took our booking rather last minute this time, and it's such a relief knowing our fur babies are in great hands. Thank you, Brandy!

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

Karen did a excellent job caring for my cats! She followed all requests in a timely fashion. We arrived home to happy cats.

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Mary Jo W.
Drop-In Visits
5.0 out of 5 stars

Peyton was awesome with our puppy Luna! She let us know what they did, kept us updated, and even took her for a walk during our drop in visit. Would recommend and have her come again!

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

Tiana has done such a good job letting our puppy out for her lunch time breaks and walks!! We trust her completely and are so happy we found her!

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Jenna G.
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.

Why Choose Rover?

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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 to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for pet sitting - Windsor

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Sitters in Windsor average 7
repeat pet sitting clients

FAQs for Pet Sitting - Windsor

Frequently asked questions about Rover

The average cost of Pet Sitting in Windsor on Rover is $21 per visit as of October 2026. Most bookings cost between $13 and $28 per visit. 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 1,431 sitters on Rover offering Pet Sitting across Windsor. 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.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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.

Yes, you can find sitters who have experience with handling special pet needs in Windsor. On Rover:

  • 88% of sitters can help with special care needs
  • 93% 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.

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 .

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.

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