Dog Sitting Wingdale
Book a Wingdale dog sitter to watch your dog in your sitter’s home or yours.

Over 25 pet parents in Wingdale have booked dog sitting
Wingdale, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: Hi my name is Cory! I love dogs and they seem to know it right away. I have been around dogs since I was 4 years old. I have owned 2 akitas and an English bulldog . My latest Akita Diablo passed away 5 years ago and I haven't gotten another dog since his passing so currently I have no dogs. I only have chinchillas and a hamster as of now. I have a lot of experience working with dogs and they seem to feel relaxed and comfortable when in my care, making this the perfect job for me. I know how to approach these animals in a way that is non-threatening to reduce their anxiety and to help them relax. I can help to maintain the routine they are used to, so they will not get anxious or feel so alone while their owners are away. I have extensive knowledge concerning the different breeds of dogs and I know how to take care of them properly. I understand that some breeds have special needs and that the age of the dog will play a major role in how to take care of them. You can depend on me to provide excellent service and to take great care of your dog/dogs. I know what questions to ask to make sure I understand their specific needs. I will be full time dedicated to your furry child, providing walks and play time as much as needed! There is nothing I wouldn't do to make your dog feel comfortable and keep their schedule to your liking. Please provide a list with your dog's habits so I can make sure they feel at home. Don't hesitate to contact me, I am very flexible with my time, and I will love and care for your dog as my own. I'm currently off from work during the summer and during the school year I only work part time at an elementary school down the road from me (2 1/2 hrs) , So I'll have plenty of time to play with your pups! I will do anything to make your pup feel comfortable and at home away from home during his stay with me. I love detailed instructions so please feel free to let me know everything about your pet! I have a fenced in yard and 2 children who are huge dog lovers who would love to keep your dog(s) busy and keep them company!
About: Growing up, I had a Lab and then a Boxer and two cats. I've also helped my aunt at the doggie daycare she runs out of her home where she often has more than 10 dogs at a time. Everything from a Great Pyrenees to German Shepherds to Doodles to Yorkies. And it's always so much fun! The care I'll give your pets will really depend on them and their needs. There's a very large unfenced grass area behind my apartment building that would be perfect for walks or play. And there are multiple parks in the area too we could explore. At yours, I'd keep whatever their normal routine is. Whether that's taking walks, throwing the ball or just sitting and chilling and scratching butts. Their butts of course! There's a very large unfenced grass area behind my apartment building that would be perfect for walks or for play. And there are multiple parks in the area too. At yours, it depends what you need. We could take walks, throw the ball or just sit and chill and scratch butts. Their butts of course!
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 :)

About: I work at an animal rescue with all different types of dogs. From 4 week old puppies, to 14 year old curmudgeon-y dogs. I am ASPCA certified, and I know how to read a dog’s body language. I have experience and confidence measuring, and administering medications. Making sure that your dog(s) are safe, healthy, fed, and walked are my top priority, and I’m looking forward to meeting your fur babies! I work part time at an animal rescue, and much of my day is empty. I do not work Wednesdays or Thursdays. I have limited availability on Fridays and Saturdays I will respect your pets boundaries, and will always be sure to keep your home clean and comfortable. Your fur baby, home, and belongings will be safe and sound.

About: I have been a volunteer for the Humane Society in a few places I lived in. My full time job also had me working with dogs on various pet friendly projects. I am very mild mannered and easy to get along with. Dogs tend to feel comfortable around me. I am also very active and can play with dogs and provide them the energy and exercise they need. I also was a member associate for Scenthound briefly in 2025. I have am very reliable and dependable and if I take on a project, will do all out and make sure it is done to the fullest extent. I am doing this as much for my love of dogs, as I am doing it for the paycheck. I look forward to making some new friends; both human and of the four legged variety. Right now I am wide open. Advance notice though is preferred. I currently between jobs sp some things pop up last minute. Thank you much! I give them plenty of love and attention and make them feel so Important and special. I will take them on walks, play, cuddle etc.

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.
About: I have over 10 years of experience as a dog walker and pet sitter from puppies to high-need senior dogs. I offer a compassionate, confident presence that will keep your pets comfortable and at ease while you’re away. I currently have open availability for dog sitting services including the upcoming holidays. I’m also available for drop ins or walks after 4pm. I’m happy to accommodate you’re pet’s regular routine as much as possible! I’m attentive and tuned into your pet’s needs. Safety is my number-one priority then of course fun! I will take the time to get to know the specific needs of your pet to ensure that they have the highest level of care and comfort.
About: I just got out of the Army after 8 years and had my best friend with me the whole way, a German Shepard named Mac. Sadly he passed about a year ago and I would love to have a new companion but I'm going back to school in the fall and need to focus on that. However, in the mean time I have the whole summer free to care for other's dogs. I live in a house with a large, fenced in yard and all the free time in the world. I'd love to have a dog to play with a d go on walks with. I currently have no obligations until September so I can devote 100% of my time and energy to your pup. Their care will be my full-time job. I have a large, fenced in yard and no other pets or children. I live on a large street perfect for walks and near the rail trail too.
About: If you’re looking for someone to just drop a bowl of kibble and scroll on their phone, I’m probably not your person. But if you want someone who will treat your pet like a misunderstood genius or a retired diplomat, we’re going to get along great! I work for the MTA as a train operator in the city, but on my days off I love taking my corgi Zuko on long walks and playing in our yard. I've had dogs and cats since I was young, and have a special affinity for all animals. If you want your fur baby treated like the king or queen they know they are while you're away, look no further! I am currently off Mondays, Tuesdays, and Wednesdays so I will have the full 24 hours of those days to walk, play, entertain, and care for your pets. I have a large unfenced yard on a very quiet street off the main road. I also have a extremely friendly and energetic corgi named Zuko who will assuredly be your pets new best friend. There will be tons of playing, running, fetch and more to ensure your pet has the best experience staying at their home away from home.
About: I have been taken care of animals since I’m 25 dogs and cats me and my wife love Animals we have French bulldogs and 2 cats I work full time but have a lot of spare time and looking to do something I love which is taken care of peoples animals Walk my dogs and have a big yard I take them out in to play and run around so I’m always with my dogs and cats
About: I’ve had animals my whole life growing up and currently have my own pets now. I’ve worked in an animal hospital as a Vet tech assistant/kennel manager for a few years. I then after that worked for my local shelter for about 10 years as a kennel worker and I was head of our dog behavioral team. I know how to read dog body language, and give meds if need be. I am a balance dog trainer that makes her own schedule, I work around my pet setting schedule! I'm currently a dog trainer and make my own schedule, I can provide pet sitting when ever needed because I can make my schedule around when I need to pet sit! I would treat my client’s pets like they were one of my own pets. I would do what ever I can to make your animals feel comfortable while you are gone.
About: Through my life, I have been a pet parent for several dogs of different ages. Family, friends, and clients have trusted me with their pets since a young age. Dogs from all ages are welcome including those with dietary and medical needs. I’ve made the decision to leave the banking industry after several years to pursue happiness and focus on my passions. Having a flexible schedule allows me to give your pet the care it needs from potty breaks to overnight stays. I love going for walks and hikes and would love for your pet to attend. As a house sitter, I provide specialized care for each pet, ensuring their happiness and safety at all times. My experience includes administering medication as well, if needed.

About: I have 2 dogs, Australian Shepperd hound mix and a Chihuahua mix. Previously had a Bichon Frise mix (Rip). I will love your dog just like my own. I can do drop ins, walks or pet sitting. I love sitting on the floor with my own dogs and sing life away (not a very good singer but my dogs loves it) i can do the same for yours. Lol I am available full time. Monday through Friday. Saturdays available at my own discretion. If needed i can make arrangements. Although i love all dogs i could care for small to medium dogs. Life full of dogs is a wonderful beautiful life. I will provide the best care for your baby. They are our children so why not give the best for them. Working from home is boring!! I have availability for your doggie baby Monday through Friday 6pm -10pm and weekends at my own discretion. I will post availability on my calendar. I have 2 friendly dogs, 1 is high energy very playful and chihuahua is very chill. Tell me what you're dog likes and i will always try to work around that.
About: I am 24 years old and have had dogs my entire life and know how to properly take care of any dog of any size. Even though I am a dog person cats do not bother me. I graduated from Post University in Waterbury, CT. I am very easy going and super easy to work with. You can reach me at just about any time of the day with any questions or concerns. I knew I have always wanted to do something like this but, was not sure exactly where to go. I am Joe and am happy to start helping out. When I am home I am always walking the dogs and also love to throw the ball around and run with both of my dogs. As said previously I walk and play with my pups and they love to run and stay active just like myself and they have a ton of energy.

About: I’ve been a dog lover all my life , currently have five little dogs of my own so when your dog visits he will always have playmates I currently work from home so availability won’t be a problem , my wife also works from home as well, your pets will always be supervised My yard is fully fenced in an of course there will be several playmates to accompany them on there outdoor excursions, I have crates available

About: I have experience taking care of dogs and cats for families and friends, I know how to read body language and know when I've crossed boundaries. I always have patience for animals. I'm working part time so I have a lot of time available to work with pets, check in on them, and stay with them if needed. I am totally available for overnights, I'm a night owl so I can always check in with a pet and take care of them.

About: I’ve been around dogs and cats since I could walk, so caring for animals has always felt second nature. I also volunteer as a dog walker, socializer, and trainer at Danbury Animal Welfare Society, where I work with dogs of different temperaments, energy levels, and needs. My style is calm, patient, and attentive, whether your dog needs a real exercise walk, your cat needs a quiet check-in, or your older pet just needs someone gentle and consistent. I know trusting someone with your pet and your home is a big deal, so I take reliability seriously. I’ll show up when I say I will, pay attention to your pet’s routine, and send clear updates so you know they’re safe, happy, and cared for. I currently work full time, but my evenings and weekends are often free. I’m a good fit for weekend walks, evening check-ins, drop-in visits, and occasional pet care when your regular routine needs extra support. Because I value reliability, I only accept bookings I know I can show up for fully and on time. I pay close attention to each pet’s body language, comfort level, routines, and boundaries, and I never force interactions with people, dogs, or unfamiliar situations. For walks, I keep dogs securely leashed, avoid unsafe areas, and adjust the pace to the dog’s age, energy, and temperament. I’m comfortable with shy, anxious, energetic, and older pets, and I believe patience and consistency go a long way. For drop-ins, I’ll respect your home, follow your instructions carefully, check food, water, litter, doors, and gates, and send clear updates so you know how your pet is doing.
The median cost per visit for dog sitting in Wingdale is $25
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
Book and pay through Rover’s secured platform—no cash or checks required.
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 dogs like family

1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Wingdale sitters!Sitters in Wingdale average 5 repeat dog sitting clients
FAQs for Drop-In Visits - Wingdale
Frequently asked questions about Rover
The average cost for Dog Sitting in Wingdale on Rover is $22.2 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 1,823 sitters on Rover offering Dog Sitting across Wingdale. 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 Wingdale stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Wingdale choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Wingdale with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Wingdale. On Rover:
- 94% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 98% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

