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Top rated Wingdale house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“After having Jillian and being new to rover, I would prefer her over others I have utilized from this app! I felt most comfortable with her care of my 2 pups and had great communication with providing updates and pictures! Shes a lovely person and easy to connect with! Highly recommended, will use for future stays!”

About: Animals have been the heart of my home since I was a child. Growing up with Labs, German Shepherds, and Mastiffs taught me how to be a confident leader and a compassionate caregiver. Today, my black cat Squirt is my best friend, and that same love I have for him is what I bring to every pet I sit for. I pride myself on being a trustworthy and caring sitter. When you leave your pets with me, you can rest easy knowing they are in the hands of someone who genuinely loves their company. I am happy to accommodate different sizes, energy levels, and personalities—I simply love being around animals and making sure they feel safe and loved while their owners are away. I am currently not working, so my schedule is open. I want to spend my free time with animals of all kinds - making all of us happy and allowing me to feel fulfilled! I am great with animals. Dogs and cats trust me and can tell that I am a genuinely good person. I won't let anything bad happen to your loved ones on my watch!
“Jeffrey is fantastic! Very flexible and easy to communicate with, we really appreciated how willing he was to come over and meet our dogs twice before our trip. He was also more than willing to return to our house to let them outside for a quick break when we asked. Can’t recommend Jeffrey enough!”

“Stephen is a phenomenal communicator, with humans and pups. He’s very friendly and professional, and is terrific at what he does! Look forward to having him sit for our brood again soon.”


About: I’ve cared for both small and large dogs, including two small dogs and a German Shepherd. I’m comfortable with feeding, walking, routines, and providing calm, reliable care. Available for drop-ins, dog walks. House sitting/ and overnight available Friday's and Saturday's. Hours flexible except 5:00–10:00am on weekdays only. Please contact me for booking. Responsible and attentive, I ensure a safe and secure environment for your pets. I follow your routine, handle pets gently, and maintain a clean and comfortable space.
“Kevin was amazing!! He took care of our new puppy when we unexpectedly adopted and had an international trip coming up. Couldn’t have asked for someone to take better care of our pup!”

“Emma was wonderful with our 3 babies. She took her own time to come do a meet and greet. She understood all the needs and necessary care of our high needs elderly dog. She communicated well, gave multiple daily reports, and sent cute/funny stories about things our dogs did while we were away. She even sent a ton of pictures, which alleviated my anxiety about leaving them. When we returned, everything was cleaned and tidy and also well taken care of. I highly recommend Emma for your dog care needs.”

“Jessie is simply wonderful to have watch your fur fam!! She is responsible, communicative, and just a pleasure to work with. Will 100% be reaching out again in the future!!!”

About: I grew up with dogs and cats. So caring for pets has always been a natural part of my life. I believe they truly are your family. I've cared for dogs and cats for friends and more recently focusef on pet sitting in the home for their owners while they are way. I'm semi retired which gives me more flexibility to care for your sweet loved one. I'm currently working part time which gives me more flexibility to walk the dog during the day and or evening and avail on weekends as well as pet sitting for long trips. If it's a medium just small dog I can take care of your pet at my home It's a condo but we have plenty of yard to walk it and walk around the neighborhood. Although has to be on a lease. Or I can come pet sit in your house if you would prefer.
“Lily has taken great care of my dog and is very communicative. She even stayed with my pup when my heat and hot water unexpectedly went out while she was there. Super thankful for her love and care for my bebe!”

“We had a wonderful experience with our pet sitter Margaret! She took excellent care of my dog, Otto, and made sure he was happy, comfortable, and well-loved while I was traveling. I really appreciated the regular updates with pictures and great communication—it gave me so much peace of mind. Highly recommend to anyone looking for a reliable, responsible, kind and caring pet sitter!”

About: My earliest memories feature dogs and cats, and they have been in my life since the age of three. Frankly, it's difficult to imagine my life without them. I have been taking care of my own, family and friends furry companions from the age of ten. I'm here for the snuggles, pets, playtimes, walks, potty breaks, litter changes and the quiet times too. From tiny, eight week old puppies, prime adults and elderly dogs that require a different kind of care and patience, to rambunctious kittens and their chill adult counterparts, each animal has a personality of their own; I'm here for them all. When people ask if I'm a cat or dog person, for me there isn't a choice; it's both! I've had experience with: - House and command training puppies from the age of eight weeks and up - Daily walks, usually between 30 min minimum to 2-3 hours; I love walks too, so it's a win-win 🐾 - Administering oral and topical medications to canines; mouths, eyes, and ears - Playtime! Or just keeping them quiet company, if that's what they prefer. - Dropping in and checking on our feline babies: changing litter boxes, feeding, play and keeping them company. I love spending time with cats of any size and stage. I am currently working part-time in food/hospitality, and begin seasonal event work in the springtime so my schedule is flexible. Currently, I have flexible availability for walks, drop-in visits or house-stays on Monday, Wednesdays, Fridays and Saturdays. When dropping in for a visit at a client's home, I always make sure to keep the space secure and clean for our four-legged friends. Pet owners can rest assured that their dogs will be engaged with and supervised, and cat people will know that their kitties are in a safe, calm environment. Animals are special to me, and I aim to treat them all as if they are my own.
“Carlie was not only very professional but so kind to our Gigi. I highly recommend her, because she is very knowledgeable about your pet, as well as has a soft spot to make them at ease and relax.”

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

“Christine is a down-to-earth person who is easy to talk with and pays attention to important details. At our meet & greet, she asked good questions that reflected her experience and commitment to making both pets and their owners feel comfortable with her. My young adult cat Suki had never been left alone with someone she didn’t already know. In my absence, however, Christine eased her way into Suki’s territory by setting the right balance between showing her some quiet attention and giving her the time and space she needed to adjust and come out of her shell. The photos Christine sent me proved that once she had won Suki over, the little kitty was her sweet, affectionate self and the two of them had a delightful time together! I will be asking Christine to Suki-sit in my house again!”

About: I’ve been taking care of dogs and cats ever since I was a little girl. I got my first dog when I was 5 and I’ve been loving them ever since. When she got old, I was her main caregiver so I have good experience with senior dogs. I’m currently unemployed so dog sitting and walking and any other side hustles take up majority of my time. The rest of my time is spent traveling or creating art. I live close to a lake so I can bring your dog on many adventures! I love going for walks and hikes, especially with a furry friend. My yard is not fenced in so if you’re planning on boarding please keep that into consideration.

About: I am a nursing student who works in healthcare. I have become the go-to pet sitter for my coworkers and family friends. I love helping people feel comfortable going on vacation and relaxing knowing that their fur babies are well taken care of. I have taken care of older pets as well as those with medical needs. I work in healthcare which allows me to have full days available to care for pets. I also work closely with my sister who helps me if I have a long work day with walks or feeds if needed. I like to care for pets as much to the clients preference. I like to have them write out the daily cares of their pets and any concerns or requests that they have while I’m caring for their pets. I’m happy to adjust to the needs and preferences of each individual pet.
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.
“God/Goddess thank you for Katie & her hubby too. Quilly was so so happy in the pictures and when I came home. Incredibly trustworthy and friendly lady (neighborly too! ) to care for pup.”

Over 47 pet parents in Wingdale have booked house sitting
How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Wingdale is $70
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 house 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.
Sitters in Wingdale average 3 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Wingdale on Rover as of Mar 2026 was about $70 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Mar 2026, there are 551 house sitters in Wingdale. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 84% of Wingdale house sitters respond in under an hour.
House sitters in Wingdale have an average of 16 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Wingdale.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Wingdale house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
