Dog Sitting Wingdale

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

When are you returning?
Search

Over 13
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.

1 / 1
Sitter Profile Image: Ebony G.
Verified Enhanced Background Check
Ebony G.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
25 years of experience
Poughkeepsie, NY, 12601

Ebony is a lifesaver!!! Took care of our four pets for 3 days super super last minute — she is super communicative, sends pictures often, and took our dogs on a walk daily. I have a kitten and she took special care of him. Took extra time to make sure each pet felt comfy with her. She’s our go-to sitter now!

Profile image
Sarah F.
Sitter Profile Image: Bianca W.
Verified Enhanced Background Check
Bianca W.
from
$25
per visit
1 repeat client
5 years of experience
12590

About: Hi! I'm so glad you're here! I know how important it is to find someone you can completely trust with your pet and that's exactly the kind of care I strive to provide. Whether your pup needs a fun walk to burn off energy or they just want a friendly face while you're away, I'll make sure they feel safe, loved, and cared for every step of the way. I treat every pet as if they were my own, following their routine closely so they stay comfortable and stress-free. I have five years of experience with both my own and family members' dogs, giving me hands-on experience with daily walks, feeding, playtime, and providing lots of love and attention. You can expect dependable communication, plenty of photo updates, and personalized care based on your pet's unique personality and needs. I know every animal is different, and I take the time to earn their trust while making sure you have complete peace of mind. I currently work part-time, giving me flexibility for dog walks and drop-in visits throughout the week. I'd love the opportunity to meet you and your furry family member! Your pet's safety and well-being are always my top priorities. I understand that every pet has their own routine, personality, and needs, so I'll take the time to follow your care instructions carefully and make sure they feel comfortable during every visit. Whether we're out for a walk or spending time together at home, I'll provide a calm, caring, and dependable environment while treating your pet and your home with the utmost respect. My goal is to give you peace of mind, knowing your pet is in safe and caring hands. Here are the Services I offer and What to Expect: 30 Minute Dog Walks include a fun stroll around your neighborhood or a nearby trail to give your pup the exercise, fresh air, and mental stimulation they need during the day. 30 Minute Drop-Ins include potty breaks, feeding, playtime, and of course plenty of snuggles to keep your pet happy and comfortable while you’re away.

Sitter Profile Image: Rachel O.
Verified Background Check
Rachel O.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
57 reviews
26 repeat clients
20 years of experience
Bethel, CT, 06801

Rachel is the best! Took such good care of our girls when we were away and they seemed very happy with her, I loved all the photos updates. She’s the best!!!

Profile image
Jennifer M.
Sitter Profile Image: Courtney C.
Verified Enhanced Background Check
Courtney C.
from
$35
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Brewster, NY, 10509

She is amazing and takes full care of your fur babies! Recommend 10/10!

Profile image
Solomon P.
Sitter Profile Image: Natalie B.
Verified Enhanced Background Check
Natalie B.
from
$40
per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
30 years of experience
Brewster, NY, 10509

Prompt, professional and reliable - looking forward to working with Natalie again!

Profile image
Brian S.
Sitter Profile Image: Gabriela G.
Verified Enhanced Background Check
Gabriela G.
from
$36
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: Christine A.
Verified Background Check
Christine A.
Star Sitter
from
$44
per visit
4.9 out of 5 stars
99 reviews
33 repeat clients
33 years of experience
Stanfordville, Stanfordville, NY, 12581

Christine was not only friendly and helpful but she was understanding of our dog’s breed and gave us such a piece of mind! She went above and beyond making it easy to highly recommend her to anyone looking for someone to watch their pup. Thank you Christine!

Profile image
Amanda R.
Sitter Profile Image: Karif & Natalie J.
Verified Enhanced Background Check
Karif & Natalie J.
from
$18
per visit
30 years of experience
Poughkeepsie, NY, 12603

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

Sitter Profile Image: Jillian A.
Verified Enhanced Background Check
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: Devon G.
Verified Enhanced Background Check
Devon G.
from
$25
per visit
10 years of experience
Carmel, NY, 10512

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.

Sitter Profile Image: Denise S.
Verified Enhanced Background Check
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: Julia M.
Verified Background Check
Julia M.
from
$33
per visit
7 years of experience
Brookfield, CT, 06804

About: I've been taking care of my own dog since we first got her 7 years ago, and I also used to volunteer at the New Milford Animal Shelter. My family fosters animals (both cats and dogs) from Because 4 Paws in New Milford, so I have some basic experience with administering medicines and helping others administer medicines. I've also been a dog sitter for 3 different families. I recently moved back to the east coast and am looking for some side work while I hunt for a full time job. I'm not sure when that will be, so I'm trying not to set my availability too far out, but am still flexible for now! Depending on what the owners are comfortable with, I would love to take the dogs out for a walk at a nearby park or walking trail. We have four cats at our house that are wary of new animals, so I am unable to pet sit at my residence. However, I am willing to spend time with your fur babies at your house or preferred location, and will follow whatever instructions necessary to ensure the comfortability of you and your pets.

Sitter Profile Image: Joseph M.
Verified Enhanced Background Check
Joseph M.
from
$25
per visit
1.0 out of 5 stars
4 reviews
10 years of experience
Danbury, CT, 06811

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

Sitter Profile Image: Jamie B.
Verified Enhanced Background Check
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: Stan R.
Verified Enhanced Background Check
Stan R.
from
$30
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
1 year of experience
Pleasant Valley, NY, 12569

I'll definitely use Stan's services again. He was accommodating, quick to respond and great with my dogs.

Profile image
dawn b.
Sitter Profile Image: Alexa F.
Verified Background Check
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: Samantha M.
Verified Background Check
Samantha M.
from
$125
per visit
5.0 out of 5 stars
26 reviews
5 repeat clients
15 years of experience
Dover Plains, NY, 12522

Wonderful experience - we had to rush out of town twice because of an elderly parent’s health. Samantha was there for us both times even though it was short notice. She saw to our cats needs and even helped out with an issue with unplugging a machine that was left running. Wonderful lady!!!

Profile image
Virginia O.
Sitter Profile Image: ATHENA M.
Verified Enhanced Background Check
ATHENA M.
from
$20
per visit
4.2 out of 5 stars
5 reviews
5 repeat clients
18 years of experience
Carmel Hamlet, NY, 10512

About: I've been taking care of dogs for over 12 years. And love them like they was family. And I watch all my friends and families dogs. I also work for wag. I have open availability for boarding. My favorite animal is a dog i always wants to be with dogs. ( i use to own cats too incase any feline friends need. I had 4 dogs growing up and as a child it was my job to care for them. When my parents sold the house because of their split they split the dogs

Sitter Profile Image: Nikki C.
Verified Background Check
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: Tiana L.
Verified Enhanced Background Check
Tiana L.
from
$25
per visit
10 years of experience
Poughquag, NY, 12570

About: I’ve been caring for dogs for over 10 years and know firsthand how important consistent, detailed care can be. My own dog has GI issues and requires a very specific diet, medication, and feeding routine, so I’m very comfortable following special instructions and keeping a close eye on changes in appetite, behavior, and routine. As a registered nurse, I’m dependable, observant, and used to being detail-oriented. I’m happy to help with walks, feeding, medications, playtime, litter box care, and plenty of updates and photos while you’re away. I work a set nursing schedule and have availability on select weekdays, evenings, and weekends. I’m happy to work around your pet’s normal routine and can be flexible with drop-ins, walks, feeding times, and medication schedules when planned in advance. I take pet care seriously and always follow the owner’s instructions closely. I pay attention to feeding, medications, bathroom habits, behavior, and anything that seems out of the ordinary. I’m careful with doors, leashes, gates, and each pet’s individual routine, and I’ll send updates and photos so you know how they’re doing while you’re away.

1 / 1
View more

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. 1. Search

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

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog sitting - Wingdale

Select a filter and find qualifying sitters offering dog sitting.

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 September 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 September 2026, there are 1,773 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge