Pet Sitting Wingdale

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 20
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Wingdale, 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: Casey S.
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Casey S.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
• 89 reviews
26 repeat clients
16 years of experience
Wingdale, NY, 12594

“We asked Casey last minute to pop in and let Birdie out/feed him dinner. She went above and beyond, staying the whole 30+ minutes, playing with him, taking him for a walk, and leaving a treat. She was also very professional, ensuring she had all of the info before arrival. We will definitely use Casey as a sitter again!”

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Olivia B.
Sitter Profile Image: Giovanna D.
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Giovanna D.
from
$20
per visit
5.0 out of 5 stars
• 5 reviews
1 year of experience
New Milford, CT, 06776

“Giovanna is absolutely wonderful! She took great care of our two dogs and communicated with us the whole time we were away. We will definitely be using her again!”

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Katie G.
Sitter Profile Image: Stephen N.
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Stephen N.
Star Sitter
from
$50
per visit
5.0 out of 5 stars
• 37 reviews
13 repeat clients
25 years of experience
Beekman, NY, 12533

“Stephen is amazing! He’s well-versed with large breeds, and we were so happy to find someone experienced who Bowser absolutely loves walking with. He’s always punctual, and after just two walks, Bowser is already so excited to see him! It’s hard to find someone you can truly trust with your dog, and Stephen is definitely that person. Highly recommend!”

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Misbah A.
Sitter Profile Image: Kristen B.
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Kristen B.
from
$30
per visit
5.0 out of 5 stars
• 4 reviews
3 repeat clients
29 years of experience
Poughquag, NY, 12570

“Kristen was always on time and a great communicator. I highly recommend Kristen!”

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Lesly E.
Sitter Profile Image: Don H.
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Don H.
from
$20
per visit
5.0 out of 5 stars
• 7 reviews
30 years of experience
Pawling, NY, 12564

About: My name is Don H. I am a professional pet sitter, dog walker and licensed dog trainer for 30+ years. I have been in the pet industry for many years, this is what I do full-time and love every minute of it. I care for all breeds of dogs and cats and also reptiles, fish, rodents, goats, horses I will e-mail/text or phone you updates and photos of your pet while you are away. I would love to help you out whether you need a pet/house sitter, dog training, dog walking, trail walks or your dog to be transported to Vet or Groomer. Your pet will be well cared for whether in your home or ours. I am a call way. Sincerely, Don My clients will give reference to how trustworthy and experienced I am when caring for pets in your home. I have respect for your property and even go the extra mile making sure your home is maintained and your pets are safe. I will take in your mail, water plants, take out your garbage/recyclables at no charge. Overnights include picking up after your pet inside and out. Why I love dog sitting I have been around all animals my whole life, I started my journey when I became a certified dog trainer. I also worked as a Kennel Manager for a medium-size kennel in Greenwich, CT. People tell me that I have great patience and calmness when working with difficult dogs. my goal is to help owners and their pet's to become one. I have over 25 years experience as a dog trainer and pet care provider. About my yard Yes i do have a backyard. Although it is not fenced in but I have tree barriers that keeps them safe. I also am close to a dog friendly park where all dogs are on leashes. I will not take a dog off leash when he/she is in my care. My experience administering medication Yes with my kennel experience, I am very comfortable administering medication. I am also comfortable administering shots for dogs and cats. I am a full time pet care provider and a dog walker and i have been training dogs of all breeds for the last 30 years. I give all my furry guest lots of play time and walks and all of our guest hang out with us we are cage free unless your owner wants your dog to sleep in one

Sitter Profile Image: Laudymarie S.
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Laudymarie S.
from
$25
per visit
28 years of experience
New Milford, CT, 06776

About: I’ve been surrounded by animals throughout my life and have cared for pets of all shapes, sizes, ages, and personalities, from small and shy to big, energetic, and outgoing. Because of that experience, I’m comfortable adapting my approach to each pet rather than expecting every animal to respond the same way. I’m confident caring for both small and large breeds, energetic puppies, adult pets, and seniors who may need a little extra patience and attention. I’m also comfortable administering medications and following specific feeding, exercise, or care instructions. I understand that shy or anxious pets may need time and space to build trust, while more outgoing pets might be ready for playtime the second I walk through the door! Most importantly, I treat every pet as if they were my own. I’ll pay attention to the little things, keep their routine as familiar as possible, and provide plenty of love, patience, and reassurance. I also know how important peace of mind is for pet parents, so you can expect reliable communication and updates while your furry family member is in my care. 🐾❤️ Pet care fits naturally into my daily routine, and I have the flexibility to dedicate plenty of time and attention to the pets in my care. I’m happy to work around each pet’s established schedule, whether that means morning or evening walks, regular potty breaks, feeding times, medication, playtime, or simply keeping them company. I understand how important consistency is for pets, especially when their favorite humans are away, so I make maintaining their normal routine a priority. Whether your pet needs lots of activity and attention or prefers a quieter day filled with naps and cuddles, I’m happy to adjust my schedule to what makes them happiest and most comfortable. 🐾❤️ When I’m caring for your pet in your home, I want them to feel like their routine hasn’t skipped a beat. I’ll follow your instructions closely, from meals, walks, potty breaks, and medications to favorite toys, sleeping spots, and all those little quirks that make your pet uniquely yours. 🐾 Having owned and cared for animals of all sizes, ages, and personalities throughout my life, I’m comfortable with the shy ones who need time to trust, the big personalities who want to play nonstop, and the seniors who just want some extra patience and love. I also know you’re trusting me with two things that mean a lot to you: your pet and your home. I’ll treat both with the same care and respect I’d want for my own. Expect plenty of love, attention, photos, and updates, because being away from your pet is much easier when you can actually see that happy face! ❤️🐶🐱

Sitter Profile Image: Aine R.
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Aine R.
from
$25
per visit
10 years of experience
New Fairfield, CT, 06812

About: I’ve owned dogs my entire life and currently have two of my own, so I truly understand the responsibility and love that goes into caring for them. I have experience with puppies and senior dogs, including maintaining routines, reinforcing basic training, and providing patient, attentive care. Your pet will be treated like family in a safe, structured, and loving environment. Pet care is already a central part of my daily routine. I have two dogs of my own, so my days naturally revolve around scheduled walks, feeding times, play, and plenty of attention. I’m very structured and organized, which makes it easy for me to maintain consistent routines and follow specific care instructions. I am currently home full time and am available for drop ins or house sitting when needed. I am flexible and can accept last minute bookings! Pets in my home are treated like family. I provide a safe, clean, and structured environment with consistent routines, regular walks, and plenty of attention. I follow each pet’s schedule closely to keep them comfortable and stress-free!

Sitter Profile Image: Celina I.
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Celina I.
from
$20
per visit
5.0 out of 5 stars
• 28 reviews
8 repeat clients
6 years of experience
Poughkeepsie, NY, 12603

“Celina is so pleasant, my puppy really took to her. I look forward to contracting her services again very soon.”

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Ray R.
Sitter Profile Image: Allison G.
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Allison G.
from
$20
per visit
5.0 out of 5 stars
• 1 review
1 repeat client
25 years of experience
Brewster, NY, 10509

About: I’m a dependable, caring pet lover who understands that pets are part of the family. I’ll treat your pets like my own, giving them plenty of attention, affection, exercise, and playtime while keeping their normal routines in mind. I’m responsible, communicative, and happy to send updates and photos so you can feel confident your pets are happy and well cared for while you’re away. I am available early mornings, mid-mornings, afternoons and evenings :) I will do my best to work with your time and day requests as a daily, weekly, or on-call request. I care for every pet based on their individual needs, personality, and normal routine. In a client’s home, I make sure pets are fed, walked, played with, and given plenty of attention and affection. I’m happy to follow any special instructions, including feeding schedules, medications, or favorite activities. I also keep owners updated with photos and messages so they can relax knowing their pets are safe, happy, and well cared for while they’re away.

Sitter Profile Image: Iza P.
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Iza P.
from
$45
per visit
5.0 out of 5 stars
• 34 reviews
14 repeat clients
20 years of experience
Lagrangeville, NY, 12540

About: Hi my name is Izabela. I have 2 amazing kids and 3 dogs :). I love spending time outside and go for long walks. Teaching my kids all about different breads. We make sure that our home is safe and fun for everyone. I love to send a lot of picture so you can see how is your dog day is going so be prepared here from me a lot 😂 I will love to meet you and you pup :) Few adds to the service : Daycare drop of starting at 7am pick up any time before 6pm after that every hour is $10 extra . Before 7am extra charge too . Overnight stay is 24 hours after that every next hour $10 extra You have to provide food for you dog . If not provide there is extra charge of $5 for each day ( I make my own food and treats ) Thank you for you understanding and we love to meet you :)

Sitter Profile Image: Denise S.
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Denise S.
from
$32
per visit
40 years of experience
Brewster, NY, 10509

About: I’ve been dog and cat sitting all my life. I also fostered a mid-size mixed terrier. I have two cats of my own. I love how all animals have amazing personalities! I can do dog walking, cat check ins with waste clean-up or over nights which ever you may need. I know how to administer meds to both cats and dogs. It is so important to have your furry loved ones pampered while you are away! I am retired so my availability is flexible. I also enjoy sending photos of your four legged loved one while you are away! I have also watched chickens, turtles, guinea pigs, snakes and iguanas. Looking forward to hearing from you! I am retired so I have a flexible schedule! I can go during the day or stay overnight at your home. Whichever you feel most comfortable with would work! When I come to your house, besides walking/feeding, I do waste cleanup as well. Of course, playing is a must! I will definitely send photos and videos so you know how your furry family member is feeling!

Sitter Profile Image: Jamie B.
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Jamie B.
from
$30
per visit
25 years of experience
Pleasant valley, NY, 12569

About: I’ve loved animals for as long as I can remember. I rescued my first dog from the local humane society when I was 11, and that experience started a lifelong passion for caring for animals. Before becoming a nurse, I worked as a veterinary assistant for two local animal hospitals where I gained valuable hands-on experience with animal care and handling. I developed skills in basic training, puppy socialization, reading animal body language, medication administration, subcutaneous fluids, nail trimming, grooming, and bathing. I also volunteered for several years with a local dog rescue as a foster, helping provide temporary homes, structure, and love for dogs before their adoptions. Many needed socialization, basic training, and a calm environment to help them thrive. I later served as the rescue’s foster and event coordinator until 2020. Today I share my home with three of my own beloved dogs. One of our previous dogs had epilepsy and required frequent monitoring and medication, which gave me additional experience caring for pets with medical needs. In my free time I enjoy traveling, camping, hiking with my dogs, training with our Belgian Malinois, and watching my daughter ride her horse. Caring for animals has always been a true passion of mine, and I treat every pet as if they were my own. My goal is for you to have complete peace of mind knowing your pets are safe, loved, and well cared for while you’re away. I’m a nurse who works three 12-hour shifts each week, which gives me several days off to dedicate to caring for animals. I truly enjoy spending time with pets and making sure they feel comfortable, safe, and well cared for while their owners are away. My schedule is fairly flexible on my days off, and I’m happy to work with you to meet your pet’s individual needs and routine. Please check my calendar for availability and feel free to reach out with any specific requests. I will always do my best to accommodate and treat your animals with the same care and attention I would give my own. At this time, I’m unable to host dogs in my home, but I’m happy to care for them in the place they feel most comfortable—your home. I offer drop-in visits, dog walking, and extended daytime care depending on your pet’s needs. I understand how important it is to know your pets are safe, happy, and well cared for while you’re away. My goal is to provide dependable, personalized care in a calm and compassionate environment, treating your pets with the same attention and kindness I would give my own.

Sitter Profile Image: Jillian A.
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Jillian A.
from
$25
per visit
5 years of experience
Hopewell Junction, NY, 12533

About: As a college student who genuinely loves animals, I bring both enthusiasm and responsibility to every pet I care for. I have experience watching and caring for dogs of different sizes and temperaments, and I’m very comfortable with daily routines like feeding, walking, playtime, and basic grooming. What sets me apart is my patience and attention to each dog’s individual needs—I understand that every pet has their own personality and comfort level. I’m especially attentive to safety and making sure dogs feel comfortable and happy while their owners are away. I can handle energetic dogs who need lots of exercise as well as older dogs who require a gentler approach and extra care. I’m also dependable, communicative, and will keep you updated with photos and messages so you always know your pet is in good hands. As a college student, I have a flexible schedule that allows me to dedicate quality time to pet care. I’m available most weekdays around my classes and have open availability on weekends. I can accommodate morning, afternoon, and evening visits, and I’m happy to work with your schedule to make sure your pet gets consistent care, attention, and companionship. Your pet’s safety and comfort are always my top priorities. In your home, I will follow all care instructions closely, maintain your pet’s normal routine, and ensure a calm, clean, and secure environment. I’m attentive to details like locked doors, safe walking practices, and keeping harmful items out of reach. I also take time to build trust with each pet so they feel relaxed and cared for while you’re away. I will keep you updated regularly so you feel confident your pet is safe and happy.

Sitter Profile Image: Alexa F.
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Alexa F.
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
3 repeat clients
3 years of experience
Bethlehem, CT, 06751

About: Hi! I’m Nicole, a 27-year-old animal lover with hands-on experience caring for both dogs and cats. I’m confident in providing attentive, reliable care tailored to each pet’s needs. I’m friendly, patient, and genuinely enjoy spending time playing, walking, and bonding with animals. I look forward to meeting you and giving your pet the care and attention they deserve! I am normally available Wednesday and weekends, For more descriptions and availability check my profile information, can’t wait to meet your family! ! ! I am currently available on Wednesdays, Saturdays, and Sundays only, and I make sure to dedicate focused, quality time to each pet during those days. At the moment, I don’t offer care in my own home since I have multiple pets. However, I’m happy to provide care in your home or take your dog out for walks. I make sure pets feel comfortable in their familiar environment while sticking to their usual routine.

Sitter Profile Image: Nikki C.
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Nikki C.
from
$32
per visit
5.0 out of 5 stars
• 7 reviews
13 years of experience
Brewster, NY, 10509

About: I have worked for a company where a strict protocol was needed to be followed regarding watching any animal. Between walks,feeding, medicine etc I would follow when caring for your pet along with having my own at home. My husband is also a trainer as well so we have experience with almost every breed and temperament ! I am home 24/7 so I would have all day home with your furry friend. I can do long term or short term and I am also very flexible and respond quick ! Not only Will I be giving your furry friend love and attention but I have two pups that love to run and play who will also be able too! They get along with everyone and are super playful!

Sitter Profile Image: Alesandra P.
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Alesandra P.
from
$50
per visit
5.0 out of 5 stars
• 13 reviews
3 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

About: I grew up around animals, from birds and hermit crabs to cats and dogs, my household has always been filled with pets. I have also fostered medically fragile dogs and volunteered at the Westchester Humane Society. I am passionate about ensuring all animals receive the best possible care and I will give your pet the same love I give my own. I currently work part time and I’m a full time grad student, but I have my own transportation so my schedule is open and flexible. I will schedule a meet and greet with you and your pet to learn all about their unique quirks, likes, dislikes, and routines prior to beginning services with them. I ensure a safe environment by using non-retractable leashes on walks and will send you updates while I am with your pet. Your pet's safety is my top priority.

Sitter Profile Image: Phalisity G.
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Phalisity G.
from
$15
per visit
4.8 out of 5 stars
• 18 reviews
5 repeat clients
10 years of experience
Wappingers Falls, NY, 12590

About: I have raised many puppies in my 10 years of experience. I like to take my dog and other fluffs on long walks through different parks and hiking trails. We always start the day with a high energy run/play at the park to get as much exercise in as possible. Throughout the day we go on shorter more frequent walks to keep her using the potty and help stay active. Our nightly walk consists of a long walk around our neighborhood to get out any extra energy so we can have a great nights sleep! I like to reward with treats and I don't mind animals on the furniture. Currently, I am a stay-at-home mom which makes me able to care for fluffs all day long. I still like to get in my exercise and taking the fluffs with me help keep me busy. I have a 4 month old puppy of my own who has MANY toys and places to sleep. She is very outgoing and house trained. I have space to crate your fluff baby if you'd like - please bring your own crate. I can also do basic puppy training as well - sit, lay, stay, handshake etc. I will also provide pictures and videos throughout our stay!

Sitter Profile Image: Natalie B.
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Natalie B.
from
$40
per visit
5.0 out of 5 stars
• 11 reviews
2 repeat clients
30 years of experience
Brewster, NY, 10509

“Natalie was so sweet and warm! She was amazing and patient with my baby. I felt very at peace with her coming over and she sent me so many great photos! She is trustworthy and I can’t wait to have her watch Crispy again.”

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Dana R.
Sitter Profile Image: Gabriela G.
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Gabriela G.
from
$40
per visit
5.0 out of 5 stars
• 6 reviews
2 repeat clients
10 years of experience
Danury, CT, 06811

About: I’ve been caring for my own dogs as well as pets of family and friends since a young age, and I understand how important it is to find someone you can trust. I treat every pet as if they were my own—ensuring they feel safe, loved, and well cared for while you’re away. My dog is friendly, well-socialized, and enjoys playing with other pets. With your permission, I’m also happy to provide high-quality photos during each visit, so you can see your pet happy and content. I currently work full-time in a hybrid position, which means I’m home about 3 out of 5 weekdays. I’m also available most weekends and enjoy spending time outdoors. During the warmer months, I often take my dog to the dog park for play and exercise. Your pet will receive plenty of attention, care, and companionship, whether we're relaxing at home or enjoying time outside. I do my best to ensure each pet feels safe, happy, and part of the family during their stay. I have an open, unfenced yard, so for safety, all pets will be leashed while outside. We also have a spacious deck where your pet can relax and enjoy the summer breeze. Inside the home, your pet will be free to roam and play under supervision. My own dog is friendly and happy to provide companionship if your pet enjoys socializing. I have a medium-sized crate available if needed, and plenty of toys to keep your pet engaged. Fresh water will always be available, and your pet’s comfort and safety are my top priorities.

Sitter Profile Image: Angelica R.
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Angelica R.
Star Sitter
from
$160
per visit
5.0 out of 5 stars
• 18 reviews
4 repeat clients
5 years of experience
Stanfordville, NY, 12581

About: Hey there! My name is Angie! I’ve taken care of dogs for 7 years. I have a Standard F1B goldendoodle who is 4 years old, a Mini F1BB goldendoodle who is 3 years old and a Newfoundland who is 8 months old! I am an experienced sitter who you can trust to take amazing care of your pup. I take any (and all) opportunities to snuggle and go on fun adventures with dogs. Some people have told me I’m a dog whisperer at times… I have yet to prove them wrong. I’m currently a nanny for a 2 year old baby. My schedule varies weekly so i do have alot of time on my hands throughout the week. I am available almost every weekend as well! I prefer sitting at clients home, with that being said i will be attentive outside and inside. I will make sure dogs are safe outside whether there’s a fence or just making sure they are safe and away from the road. I also would make sure they will not wonder off, attentive is my #1 priority. Making sure their safe in their home and not being mischievous is also a big priority for me and your furry babies!

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The median cost per visit for pet sitting in Wingdale is $25

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Sitters in Wingdale average 5
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FAQs for Pet Sitting - Wingdale

Frequently asked questions about Rover

The average cost of Pet Sitting in Wingdale on Rover is $22 per visit as of October 2026. Most bookings cost between $15 and $35 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 1,829 sitters on Rover offering Pet Sitting across Wingdale. 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 Wingdale. On Rover:

  • 90% of sitters can help with special care needs
  • 93% 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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