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 6
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: Caprice G.
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Caprice G.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
2 repeat clients
12 years of experience
Windsor, VA, 23487

About: What sets me apart is the genuine love and experience I bring to every pet I care for. I have over 12 years of pet-care experience and am a pet parent myself to three Chihuahuas, including a senior dog. Because of this, I understand the extra patience, attention, and care that senior pets can need. I’m comfortable caring for puppies, adult dogs, and senior pets, and I’m happy to accommodate each pet’s individual routine and personality. Whether your pet is energetic and playful or prefers a quiet, relaxed environment, I’ll make sure they feel safe, comfortable, and loved while you’re away. 🐾❤️ Pet care fits naturally into my daily routine because I stay home full-time. This allows me to give pets plenty of attention, companionship, playtime, and care throughout the day. I’m able to work around each pet’s normal routine, including meals, potty breaks, walks, medications, and plenty of love and cuddles. 🐾❤️ Because I’m home most of the day, your pet can have someone nearby rather than being left alone for long periods. I truly enjoy having animals around and love making them feel comfortable, safe, and at home while their families are away. I care for every pet based on their individual needs and the routine their family has established. In my home, pets are treated like family and receive plenty of attention, playtime, potty breaks, walks, meals, and lots of love. When caring for pets in their own home, I make sure to keep their normal routine as consistent as possible so they feel comfortable and secure. I’m happy to provide walks, feeding, fresh water, litter box care, playtime, cuddles, and basic medication care when needed. I understand that every pet is different, so I take the time to learn their personality, schedule, and specific needs before their family leaves. My goal is always for your pet to feel safe, loved, and well cared for while you’re away. 🐾❤️

Sitter Profile Image: Mia M.
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Mia M.
from
$20
per visit
5.0 out of 5 stars
• 7 reviews
1 repeat client
3 years of experience
Suffolk, VA, 23434

“I submitted a last minute request for drop-in visits and Mia accepted without hesitation. My pups warmed up to her right away and loved all the pets and attention.”

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Brianna P.
Sitter Profile Image: Kayla S.
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Kayla S.
from
$20
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
5 years of experience
Suffolk, VA, 23434

About: Newer to Rover but have been pet sitting independently for 5 years. I love all animals and will care for your fur baby as if they are my own. I have two dogs as well! I am comfortable with all dog sizes and have experience with dogs as small as a chihuahua and as big as a great dane. I would love to care for your baby! I work full time but am available for weekend and evening time drop ins and walks ! I am physically fit and can walk your pups for as long as you need! I adore all animals and can care for them however you specify ! I will always treat your pet as if they are my own ! I will also always make sure to follow your exact specifications to ensure your baby is getting the best care possible. They can always expect lots of love too ❤️

Sitter Profile Image: Madison T.
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Madison T.
from
$17
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
13 years of experience
Suffolk, VA, 23434

“Awesome sitter. Was very patient and considerate of our baby girl and took well care of her. Also was very helpful and flexible in a last minute change to schedule. Definitely will be picking Madison again on any future trips to watch our pets”

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Rafael K.
Sitter Profile Image: Chainey L.
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Chainey L.
from
$14
per visit
5.0 out of 5 stars
• 18 reviews
4 repeat clients
5 years of experience
Wakefield, VA, 23888

“Chainey was great and was so good with my pups and she even was able to come an additional morning since our flight was delayed! Def recommend!!”

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Brandie L.
Sitter Profile Image: Brooke R.
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Brooke R.
from
$20
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
6 years of experience
Smithfield, VA, 23430

About: I have been around dogs my entire life, and caring for them has always come naturally to me. I’m a compassionate and attentive caretaker who truly understands that every dog has its own personality and needs. Whether it’s making sure they’re fed, walked, played with, or just comforted, I treat every dog as if they were my own. My lifelong experience has taught me patience, responsibility, and how to build trust with animals, which is why I know I’d be a great fit for any role involving dog care! i promise your dogs will love our fenced in dog area and have lots of fun! I am currently not working, and I have always wanted to work with animals! Dog sitting allows me to watch my own dog while also taking care of other people’s dogs and making a living for myself! we have a fenced in dog area and lots of room to run and play! I don’t allow any squeak toys in my house in case of choking hazards! And I have crates if you can’t bring your own if your dog is crate trained!

Sitter Profile Image: Jane C.
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Jane C.
from
$40
per visit
5.0 out of 5 stars
• 9 reviews
1 repeat client
17 years of experience
Suffolk, VA, 23434

About: My first two pets were 2 doggies at 9 months old. I had them for 17 years until they left for doggy heaven October 2024 and February 2025… I am not ready to fully commit again quite yet so decided babysitting and loving on others’ furbabies will help the healing. Work from home all week. Will be able to take care of them in home and overnight if needed! I will accomodate to all requests and needs. Will appreciate details such as age, allergies, health, likes and dislikes. Will treat your baby/babies like they are my own. Will walk them as I have a dog friendly neighborhood as well as a newly built dog park. The backyard is also fenced.

Sitter Profile Image: DeHaven S.
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DeHaven S.
from
$35
per visit
5.0 out of 5 stars
• 34 reviews
7 repeat clients
10 years of experience
Carrollton, VA, 23314

“DeHaven and Ashlee were wonderful with my 3 cats, they were patient and made them feel at ease. I can't reccomend them enough! I usually can't enjoy my vacation because I am so anxious about my pets, but I was able to relax knowing they are in good hands.”

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Ana C.
Sitter Profile Image: Juliet H.
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Juliet H.
from
$10
per visit
12 years of experience
Suffolk, VA, 23434

About: I have taken care of a variety of different pets with different conditions since I was a kid. I know how to administer oral medications daily and have knowledge of mobility issues as well. I have a lot of knowledge of birds as well due to me having parakeets and a conure. I would love to be considered for help of almost any animal you have! Just ask me questions and I will answer. Thank you :) I always have mondays off, but my schedule for the week is posted on that day. Due to this i need at least a weeks worth of notice for anything if i need to communicate scheduling. Thank you Learning the needs/likes of the animal to interact better and make sure they are comfortable while their trusted companion's are away. If there is a special way your pet needs to do anything, then I am more than happy to learn.

Sitter Profile Image: Mackenzie M.
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Mackenzie M.
from
$20
per visit
5.0 out of 5 stars
• 2 reviews
2 repeat clients
3 years of experience
Suffolk, VA, 23434

About: I started by watching my neighbors cat during the holidays. I then started to watch neighborhood dogs over the past year when their owners go on vacation. I’m currently a part time nanny. I have a lot of free time to spend with your loving fur babies. I have my own dog that I take care of 24/7 I would love to care for your fur babies. I also make sure they have a full bowl of water and food, also get outdoor exercise!

Sitter Profile Image: Ashlynn S.
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Ashlynn S.
from
$18
per visit
5.0 out of 5 stars
• 150 reviews
71 repeat clients
6 years of experience
Portsmouth, VA, 23707

“Ashlynn was awesome! She took such good care of our cat and young kittens and posted such great photos! I couldn’t imagine somebody taking better care of my pets !”

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Justin C.
Sitter Profile Image: Ieashaw H.
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Ieashaw H.
from
$25
per visit
7 years of experience
Suffolk, VA, 23434

About: I’ve been around animals my whole life, especially cats and dogs, so caring for them feels natural to me. I enjoy spending time with pets, giving them plenty of attention, exercise, and affection while making sure they feel safe, comfortable, and loved. I’m dependable, patient, and will always follow your pet’s routine and care instructions. I’ll treat your furry family member like they’re one of my own and keep you updated with photos and messages while you’re away. Pet care fits well into my schedule because I work PRN, which allows me to make my own hours. I occasionally work overnight shifts, and on Mondays and Thursdays I help with shipment at a clothing store from 6:00 a.m. to 10:00 a.m. Outside of those times, I have a flexible schedule and can plan around pet care. I’m committed to providing dependable, attentive care and will make sure your pet gets the time, attention, and love they deserve. When caring for pets in your home, I always respect your space and follow your pet’s normal routine as closely as possible. I’ll make sure they have fresh water, meals on schedule, exercise, playtime, and plenty of love and attention. I understand that every pet is different, so I’ll follow any instructions you leave, including medications, feeding schedules, or special care needs. My goal is to help your pet feel safe, comfortable, and happy while you’re away, and I’ll keep you updated with photos and messages so you can have peace of mind.

Sitter Profile Image: Samantha M.
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Samantha M.
from
$35
per visit
10 years of experience
Suffolk, VA, 23434

About: Hi, my name is Sam, and I’m a mom to two kids and one playful pupper! Having grown up on a working farm, I have experience caring for all kinds of animals, big and small. I’ve fostered dogs in the past, and our own pup, Leah (a playful German Shepherd), loves having furry friends. We live in a quiet neighborhood with a large, fenced-in yard on our 2-acre property, perfect for safe outdoor play. I ensure that all guest pets are treated like family, providing plenty of love, attention, and care. Your dog will enjoy playtime in our spacious yard, along with the option of walks around the property. Safety is my top priority, and I maintain a secure environment both indoors and outdoors to keep your fur baby happy and protected. I look forward to welcoming your pet into our home! I am available most days of the week, aside a local errand or traveling to my children’s school. Our guests will not be left alone for extended periods! I have a fence yard and a dog who enjoys playtime. Our neighborhood is quiet and perfect for walks as is our surrounding unfenced property for nature walks! We have a children in our home who love animals so our guests must be kid friendly! Our kids are taught to be gentle and respectful to all animals. We currently only accept guests who are house trained. Please let us know if your dog requires specifics needs or requires medication.

Sitter Profile Image: Anna B.
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Anna B.
from
$20
per visit
5.0 out of 5 stars
• 3 reviews
20 years of experience
Newport News, VA, 23601

About: You can finally relax knowing your pet will be safe, treated like family and given all the love. Hi there! I’m a stay-at-home mom located in the Hilton area of Newport News. I’m active, reliable, and available from early mornings until late afternoon. I’ve cared for everything from a home full of 7 cats and 4 labradoodles (all at once!) to countless pets belonging to friends, family, and friends of friends. I have a 6 year old son with special needs who absolutely adores pets so if you’re looking for boarding, please make sure your pet is child-friendly. During the day however, he’s in school and I will be able to cover those who may not be small child friendly. I don’t mind hopping in the car to take your pup to the park or on a trail if they need more than just a quick lap around the block. I’m a big morning person who thrives on routine but, full disclosure, I avoid rush hour or late-night driving since my son is with me after 3:30 p.m. Monday–Friday. Whether your pet needs a walk, drop-in, or a place to stay while you’re away, I am here to help. Just drop me and line❤️ I’m available Mon-Fri from 5am-5pm for walks, parks, even just a home visit and car ride if your pet just needs some 1:1 during work hours. Weekends are limited so send me a message during the week to check availability. I have a large yard but it is not fenced. My son and I enjoy walking whenever we can around our neighborhood in Hilton. I have a pet and baby proof clean home with a gentle loving child. Cleanliness is of the utmost importance to me so you won’t have to worry about anyone making a mess and it not being cleaned up.

Sitter Profile Image: Sierra T.
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Sierra T.
from
$21
per visit
2.3 out of 5 stars
• 3 reviews
1 repeat client
8 years of experience
Greenbrier West, Chesapeake, VA, 23320

About: I’ve been taking care of dogs for about 8 years and I’ve honestly always loved being around animals. I started by helping neighbors, friends, and family, and it just turned into something I really enjoy doing.I’m super patient and I pay attention to what each pet needs, because I know every dog is different. I have experience with all kinds of dogs big, small, puppies, seniors and I’m good at matching their energy whether they wanna play a lot or just chill.I’ll treat your pet like they’re my own and make sure they feel safe, comfortable, and loved while you’re gone. I also know how important it is to trust the person watching your pet, so I’ll always keep you updated and make sure you feel good about everything. My schedule is pretty flexible, so I have a good amount of time to focus on your pet and not rush anything. I’m available most days and can work around your pet’s normal routine, whether that’s walks, feeding times, or just hanging out with them.I’m also good with last-minute bookings when I can, so if you ever need help, I’ll always try my best to make it work. I always make sure pets feel safe, comfortable, and cared for, whether I’m in your home or mine. I pay attention to their behavior and needs so they feel relaxed and not stressed while you’re away.I’ll follow whatever routine you have for them and keep things consistent, and I’ll always keep you updated so you know how your pet is doing. I treat every pet like they’re my own, and I take that responsibility seriously.

Sitter Profile Image: Tyler M.
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Tyler M.
from
$25
per visit
5.0 out of 5 stars
• 1 review
15 years of experience
Corapeake, NC, 27926

About: I have experience working with animals of all breeds/species. I used to work for a boarding/daycare/grooming facility that was also connected to a vets office. I’m familiar with farm animals, dogs, cats, most small pets, and reptiles. I had my own horse for 17 years. Currently I have two German Shepherds who are both 4 years old- so I’m very familiar with working breeds! *I have experience with administering medications and animal first aid* I’m currently a stay at home mom and have full availability. More than likely my son will be with me for drop in visits- but for house sitting, arrangements can be made if necessary! With my two being a working breed we go on a lot of walks, and play a lot of fetch. But they also know how to be couch potatoes! Either way I can follow the lifestyle your pet is used to whether it be cuddles and lounging or going outside to play. I’m all about communication so pictures and daily check ins are something I like to provide!

Sitter Profile Image: Lacey L.
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Lacey L.
from
$25
per visit
5.0 out of 5 stars
• 2 reviews
17 years of experience
Portsmouth, VA, 23704

About: I have worked in multiple professional settings where I was responsible for the basic and special care of canines. Comfortable with all types of behavior and personalities to include fearful, reactive, and challenging. I balance work and caring for your pup in my day to day routine. Flexible schedule that allows me to be available even in short notice. I am incredibly diligent when ensuring the safety of your pet. Similar to children they should be monitored and not left to their own devices.

Sitter Profile Image: Opiaah J.
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Opiaah J.
from
$15
per visit
1 year of experience
Norfolk, VA, 23505

About: Although I myself am a new pet owner, I come with a strong set of skills that make me a great pet sitter. As a former teacher & a mom I’m patient, attentive, and great at keeping routines structured. I’m used to multitasking and staying calm under pressure, which means I can handle whatever your dog needs with care and focus. I specialize in caring for “hypoallergenic” dogs. I understand their unique needs and take extra care to maintain a clean environment that’s comfortable for them and safe for allergy-sensitive owners. You can trust me to provide consistent, loving care tailored just for your pup. I’m available Monday through Sunday. Whether it’s a regular weekday visit or occasional weekend care, I’m here to provide consistent and attentive support to your hypoallergenic dog. Let me know if you need flexible scheduling within these times—I’m happy to accommodate when possible. I understand that trust and safety are the most important things when it comes to caring for your beloved pet. That’s why I provide a secure and loving environment where your dog can feel comfortable and happy. I have a fully fenced yard, giving your pup a safe space to play and explore freely without worry. You can count on me to treat your dog like family, with attentive care, consistent supervision, and a focus on their well-being at all times. Your dog’s safety and happiness are my top priorities.

Sitter Profile Image: Airly S.
Verified Enhanced Background Check
Airly S.
from
$25
per visit
3 years of experience
Norfolk, VA, 23505

About: I have experience in daycare/boarding settings, i have experience with high drive dogs, I do dog sports with my own personal dog so i am pretty confident in my handling skills. I have done years of research on dog related things some including understanding body language, knowing when a dog is uncomfortable or needs to be removed from a situation, what things are good and what are bad, how to use training tools properly if needed, learning the genetics of dog breeds and just over all temperaments that certain breeds have. I grew up on a farm full of dogs and other animals ive always owned dogs especially bully breeds ive been around dogs will all ages, behaviors and sizes my family and friends all know my love for animals and how good i am with them and how much i care about them even when they arent my own. I currently am unemployed, i am a stay at home dog mom and aside from the occasional grocery store run i am at home with my dogs. I will care for your pet to the best of my ability and under any instructions that may be given to me. I will care for your pet like they are my own and keep them as safe as possible while under my care!

Sitter Profile Image: Madison J.
Verified Enhanced Background Check
Madison J.
from
$20
per visit
4 years of experience
Williamsburg, VA, 23185

About: I’ve dog sat for family, friends, and clients that resided in Philadelphia, New Jersey, and Virginia. My clients have relied on me to check on, walk, and feed their little family members. I have a little bundle of joy named Mochi. Taking care of him is my favorite thing to do. He makes me realize that I have what it takes to care for pets of all different backgrounds. :) I’m currently working transitioning into a new job and looking to use all my free time to take care of your little family member!❤️🐱🐶 🏡 Trust, Safety & A Comfortable Environment 🐾 Your pet’s safety and comfort are my top priorities! Whether your pet stays in my home or I come to yours, I’ll provide a clean, calm, and caring environment where they can feel comfortable and secure. I’ll follow your instructions closely, respect your home and routines, and make sure your pet receives plenty of attention, supervision, and care. You can have peace of mind knowing your furry family member is in a safe and loving environment while you’re away. ❤️🐶🐱

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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

Caprice did a great job with our Great Dane. She was prompt and sent plenty of photos and updates everyday. 100% would recommend!

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Erica W.
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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    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

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Popular requests for pet sitting - Windsor

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Sitters in Windsor average 6
repeat pet sitting clients

FAQs for Pet Sitting - Windsor

Frequently asked questions about Rover

The average cost of Pet Sitting in Windsor is $14 per visit as of October 2026. Most bookings cost between $14 and $24 per visit. On Rover, 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 2,269 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:

  • 89% of sitters can help with special care needs
  • 94% 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 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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