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 186
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
• 30 reviews
15 repeat clients
4 years of experience
Windsor, WI, 53598

“Taryn did a great job with George while we were away. We appreciated knowing he was in good hands and enjoyed the updates and photos she sent us. She was a great communicator, arrived when she said she would, and took care of George like he was her own. We will definitely have Taryn back to look after him again.”

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Ashley S.
Sitter Profile Image: Heather S.
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Heather S.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
• 45 reviews
8 repeat clients
25 years of experience
Windsor, WI, 53598

“We had a great experience booking Heather through Rover! Our two cats can be shy with new people but were happy to see Heather for feeding and playtime. They also take medication via pill and they had no issues accepting that from her. We received detailed updates and lots of pics. We came home to two content kitties!”

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Kristine S.
Sitter Profile Image: Emily L.
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Emily L.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 37 reviews
14 repeat clients
25 years of experience
Sun Prairie, WI, 53590

“Emily checked in on all times that were discussed, and walked Captain on the check-ins. I enjoyed all photos of Captain with his bones, on his walks, or just hanging out. The accessibility that Emily had with my apartment was great with Captain being at home and feeling like he was home and loved. I appreciated that we could contact if we were running late or coming back early from vacation, so that we could time everything out. Overall, Captain enjoyed his time a lot with Emily, and I appreciated all check-ins and photos.”

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Philip S.
Sitter Profile Image: Jen D.
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Jen D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 343 reviews
74 repeat clients
15 years of experience
Berkley Oaks, Madison, WI, 53704

“Jen was so fantastic with our two kitties. They seemed really happy and we will definitely have her back! Thanks for making our trip so carefree”

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Laura M.
Sitter Profile Image: Toni S.
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Toni S.
Star Sitter
from
$12
per visit
4.9 out of 5 stars
• 56 reviews
24 repeat clients
30 years of experience
DeForest, WI, 53532

“Toni went above and beyond! Not only did she take superior care of our little cavapoo, Bailey, she brought our garbage cans in from the curb and offered to check in on Bailey one more time if we were running late. Excellent care and service!!”

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Amy K.
Sitter Profile Image: Darshani L.
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Darshani L.
from
$13
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
10 years of experience
Windsor, WI, 53598

“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.
Sitter Profile Image: Mira D.
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Mira D.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 9 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: Hailey M.
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Hailey M.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
• 45 reviews
10 repeat clients
10 years of experience
Madison, WI, 53704

“Hailey was so great! Took such great care of my cat while I was away, couldn’t ask for better help. Very responsive and flexible with schedule that needed changing a few times. She sent pictures every drop-in and kept me updated! Definitely recommend Hailey to watch after your pets also.”

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Trevor S.
Sitter Profile Image: Katelyn R.
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Katelyn R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 49 reviews
16 repeat clients
10 years of experience
Sun Prairie, WI, 53590

“Katelyn has a kind and calm demeanor which helps settle the nerves in one of my anxious pups. She makes sure my two dogs are safe and comfortable during her drop in visits. I plan on continuing our drop in visits! Thank you!”

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Emily P.
Sitter Profile Image: Tiana B.
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Tiana B.
from
$20
per visit
5.0 out of 5 stars
• 32 reviews
12 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: Jackie G.
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Jackie G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 68 reviews
18 repeat clients
20 years of experience
Madison, WI, 53718

“Jackie is awesome! She did an amazing job taking care of our girl while we were away and then some! She is friendly, communicative, flexible and considerate. We would love to have her back again and happily recommend her to others!”

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Alicia W.
Sitter Profile Image: Michel P.
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Michel P.
from
$23
per visit
5.0 out of 5 stars
• 80 reviews
31 repeat clients
30 years of experience
Sun Prairie, WI, 53590

“Michel is awesome! She takes great care of my kitties and they love her. I feel really comfortable going out of town knowing that she will be taking care of my pets. She sends me such great photos of them also. Would highly recommend Michel!”

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Anna H.
Sitter Profile Image: Tonisha A.
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Tonisha A.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 57 reviews
16 repeat clients
30 years of experience
Sun Prairie, WI, 53590

“We had never used Rover before but our neighbors had and highly recommended it. Tonisha did an AMAZING job taking care of our little fur babies while we were unable to for two days. She came over to meet the pups ahead of time and we knew she would be a great fit. While we were away, she came over to walk, play, feed and snuggle our little ones. Tonisha took lots of pics and videos, along with updating us how things went after every visit. We will definitely use her services again and highly recommend the care with love Tonisha provided! The pups were happy to see us when we returned and I am positive they were very well taken care of:)”

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Jennifer H.
Sitter Profile Image: TAYLOR P.
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TAYLOR P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 43 reviews
16 repeat clients
15 years of experience
Madison, WI, 53704

“Taylor was wonderful with Louise. She came everyday, kept his bowl filled and spent time with him. Was very pleased with her service and she sent a bunch of photos. Thanks Taylor!!”

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Gwen G.
Sitter Profile Image: Shatoria W.
Verified Background Check
Shatoria W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 37 reviews
13 repeat clients
10 years of experience
Sun Prairie, WI, 53590

“Shatoria was absolutely awesome! She stopped in to check on my cat Olivine while my roommate and I were away for the weekend. During our initial visit, Shatoria asked a ton of questions about Olivine and her routine, some that I hadn’t even thought to bring up, which was great. During the actual visit, she passed along lots of photos of Olivine with her update. She also took a photo of her automatic feeder so I could see how Olivine had been eating, which I appreciated. I had never hired a pet sitter before, so that came with some anxiety, but Shatoria made me confident that I was leaving Olivine in great hands! I definitely know who to come to if we ever need any more help with Olivine in the future.”

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Avianna H.
Sitter Profile Image: Maria & Bryan P.
Verified Enhanced Background Check
Maria & Bryan P.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
30 years of experience
Waunakee, WI, 53597

About: We have been loving and caring for dogs for a long time. Big and small dogs; young and old. Our son and 7 year old dog are welcoming I am currently working from home and Bryan works part time. Our son is home schooled at this time, therefore, we have time and energy to help other dogs and other families We have a large yard in a quiet neighborhood; part of our yard is fenced and other part is open for additional exercise. We also walk our dog daily.

Sitter Profile Image: Lensy A.
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Lensy A.
from
$25
per visit
5.0 out of 5 stars
• 16 reviews
7 repeat clients
15 years of experience
DeForest, WI, 53532

About: Hi! My name is Lensy, and I’m excited about the opportunity to care for your pet. A little about me: I am in grad school (online) and work a hybrid job which gives me flexibility/ allows me to be remote a good amount so your furry friend isn’t alone day! I have plenty of experience looking after neighbors’ pets, from playful puppies to full-grown dogs. I also have experience with birds and cats. I can’t wait to take your furry friend out for walks, keep them entertained, and meet their unique needs. I understand it can be hard to trust someone new with your beloved pet, so please don’t hesitate to share any concerns or specific instructions. I’m here to make both you and your pet feel comfortable! I’m flexible, understanding, and passionate about keeping pets happy and active. I look forward to meeting your little companion! PS you will see a lot of photos on my profile of my family golden doodle Coco, who is my whole world😌 I I often have the flexibility to work remotely and do grad school online which allows me to be quite adaptable. I am available to do in-person visits and check-ins throughout the day, though I’m unable to provide lodging. My weekends are currently free, so I’m happy to arrange care for your pets during that time as well. Please feel free to reach out to discuss how I can best accommodate your needs! When caring for pets in my home or in my client's home, I prioritize creating a safe, comfortable, and stimulating environment tailored to each pet's needs. In my client's home, I want to be sure to know their routines. I focus on providing a stress-free experience, ensuring your pet feels comfortable and cared for in familiar surroundings. At home, I have a pet of my own, a mini golden doodle named Coco, who has taught me a lot about pet care and the importance of personalized attention. I ensure a calm, pet-friendly space where all animals can relax and feel at ease. I also maintain consistency in feeding times, play sessions, and any special care routines. I always ensure their safety and well-being is my top priority, no matter the setting.

Sitter Profile Image: Karen C.
Verified Enhanced Background Check
Karen C.
from
$15
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
35 years of experience
Windsor, WI, 53598

“Karen was fantastic with our cats! Treated them wonderfully and sent the best update pictures. Will for sure be looking into her again next time!”

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Samantha D.
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: Allison B.
Verified Enhanced Background Check
Allison B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
4 years of experience
Sun Prairie, WI, 53590

“Allison was amazing!! She took such incredible care of our dog, Macie while we were out of town. She went above and beyond, and always gave detailed updates so we could relax and enjoy our trip knowing she was in the best hands! She was so kind, always replied quickly, paid attention to details, and made our dog feel so at ease while we were away. I highly recommend Allison if you are looking for someone to take amazing care of your dog!”

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

Pet parents share their Rover experiences - Windsor

1 / 1
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

Della did great with my cat all week and was willing to jump right in with short notice. I enjoyed the daily updates and her helpful nature.

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

Awnna took great care of our cats! She administered meds to one of our cats that required 2 visits per day. She fed and played with them and made sure water bowls were filled and litter boxes scooped. Awnna did a wonderful job and we would definitely have her take care of our kitties again!

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Deborah E.
Drop-In Visits
5.0 out of 5 stars

Kirstyn is fantastic; our boys love her and she takes great care of them. Communication with her is easy. She sends pictures and details of each check-in.

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Missy M.
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
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Book with peace of mind

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

Why Choose Rover?

  • Cashless payments

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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.

Meet local sitters who will treat your pets like family

  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

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Windsor average 7
repeat pet sitting clients

FAQs for Pet Sitting - Windsor

Frequently asked questions about Rover

The average cost for Pet Sitting in Windsor 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 Pet 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 Pet Sitting. For more information on service fees, click here .

As of September 2026, there are 1,460 sitters on Rover offering Pet Sitting across Windsor. 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 Windsor 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.

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 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.

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

  • 91% of sitters can help with special care needs
  • 96% 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.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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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