House Sitting Wingdale

Find a loving house sitter to watch over your pets and your home.

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Over 20
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Wingdale, Find top rated house sitting

Prices are estimates per night. 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
$90
per night
5.0 out of 5 stars
• 89 reviews
26 repeat clients
16 years of experience
Wingdale, NY, 12594

“Casey was amazing!! We needed someone last minute to watch our pup while we were away and she responded right away and kept in constant contact the whole time she was watching him with updates and pictures. We never had to worry and will definitely use her again in the future!!”

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Christa D.
Sitter Profile Image: Jillian G.
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Jillian G.
from
$65
per night
5.0 out of 5 stars
• 28 reviews
5 repeat clients
10 years of experience
New Milford, CT, 06776

“This was my first time using Rover & I could not have had a better experience with Jillian. She came by to meet us ahead of the overnight stay and my dogs took to her immediately. Jillian is kind, caring & truly loves animals. It’s never easy leaving your pets with someone you don’t know but I felt very comfortable with Jillian knowing they were in good hands. My house was just as clean as when I left it and she even stayed longer than requested. I will absolutely book with Jillian again.”

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Lexi F.
Sitter Profile Image: Jason S.
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Jason S.
from
$55
per night
5.0 out of 5 stars
• 16 reviews
6 repeat clients
15 years of experience
Carmel Hamlet, NY, 10512

“Jason was great with our animals. He sent some photos and kept in touch letting us know how everything was going and how sweet our pets were for him. We hope to be able to book him again in the future.”

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Rob S.
Sitter Profile Image: Don H.
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Don H.
from
$50
per night
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: Jordyn K.
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Jordyn K.
from
$35
per night
20 years of experience
Millbrook, NY, 12545

About: Hello! I have cared for farm animals full time. I used to foster dogs caring for wounds basic training along with dogs with reactive issues. I have 3 of my own all large breed but very friendly, and one horse with a big personality. I am patient and compassionate all animals have their own personality and all require different care. I work only nights I am a EMT . Which leaves my days free, I can provide all day pet care including walks and or stop ins no problem I can provide comfort to the pets playing or long walks while owners are away or at work. I can stop in as many times as the owners think throughout the day for potty breaks or nights when I’m off of work.

Sitter Profile Image: Phoebe A.
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Phoebe A.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Poughkeepsie, NY, 12603

“Phoebe was amazing! She did house sitting with Zora and even though Zora was afraid of her at first, she got her to warm up fast. She texts us almost every day with pictures and took Zora on local walks on trails. Happy to have her sit again!!”

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Khristina B.
Sitter Profile Image: Julia B.
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Julia B.
from
$65
per night
5.0 out of 5 stars
• 4 reviews
10 years of experience
Brewster, NY, 10509

“Julia was amazing with my pup. She kept me in the loop with pictures of him while she stayed with him. I will be using her again in the future for sure!”

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Norville Y.
Sitter Profile Image: Timothy D.
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Timothy D.
Star Sitter
from
$130
per night
5.0 out of 5 stars
• 9 reviews
5 repeat clients
20 years of experience
Arlington, NY, 12603

“Tim is so great! Kind - big hearted - and took great care of our two Australian Shepherds while we were away. He sent pictures and updates and was so thoughtful.”

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Nicole C.
Sitter Profile Image: Alesandra P.
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Alesandra P.
from
$100
per night
5.0 out of 5 stars
• 13 reviews
3 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

“Really grateful to’ve found such a great sitter! Super communicative and of course most importantly, great with our dogs. Felt safe leaving them and our home in her care.”

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Kathryn F.
Sitter Profile Image: Alexa C.
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Alexa C.
from
$32
per night
5.0 out of 5 stars
• 2 reviews
15 years of experience
Sherman, CT, 06784

About: I have taken care of cats and dogs as well as other animals for many years both in my own home as well as at other families homes! I can be relied on to care for the animal as if they are my own and provide lots of love to them! I work as a nanny but am also home each night and my parents are often home during the day when I am not home (they are also animal lovers!). Also happy to help on weekends as well! We have an unfenced backyard but we have a dog play area with its own ramp from the house down into a fenced in area with grass and water and some shade! Inside the house we would either crate the animal at night or if they are not used to being in a crate, keep them in a room separate from our animals with plenty of air conditioning, food, water, playtime, and lots of fun time outside!

Sitter Profile Image: Michele F.
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Michele F.
from
$115
per night
5.0 out of 5 stars
• 11 reviews
2 repeat clients
11 years of experience
Poughkeepsie, NY, 12603

“Michele was fabulous!! Jasper was in great hands! She sent plenty of photos and I appreciated this! She also drove Jasper to his doggie daycare, Central Bark! This kept Jasper occupied and offered Michele a break! Although I know she would have kept him busy at home too.”

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Melissa G.
Sitter Profile Image: Katharina D.
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Katharina D.
from
$50
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
South Salem, NY, 10590

“Kat was amazing and very accommodating to our needs. She asked a lot of questions about the dogs needs before the sit and kept in communication She took care of four dogs, including a small puppy and sent lots of pictures. All of the dogs seemed happy and it worked out great. Kat cleaned up really nice and even washed the linens that she used so I didn’t have to do that when we come back.”

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Laura K.
Sitter Profile Image: Stephen M.
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Stephen M.
from
$15
per night
20 years of experience
Lagrangeville, NY, 12540

About: I specialize in reliable night and weekends dog walks and house sitting in the Hudson Valley. I don’t just check boxes—I take time to understand each dog’s unique personality, preferences, and needs. Whether it’s a playful pup who needs extra exercise or a shy senior who just wants gentle companionship, I adjust my care to suit them. I also prioritize clear, friendly communication with pet parents, sending updates and photos so you always feel connected. My goal is simple: to make every dog feel safe, loved, and at home—even when you’re away. I currently work full time but I would like to take on some dog walking and sittings on nights and weekends as I currently cannot have pets in my house. In my home or yours, I create a calm, safe, and loving environment tailored to your pet’s routine and personality. I stick closely to feeding schedules, exercise needs, and any special instructions you provide. In your home, I respect your space and your pet’s comfort, keeping things clean and consistent so your dog feels secure. In my home, I offer a pet-friendly, supervised space with plenty of attention, playtime, and rest. I always communicate openly and send photo updates so you know your pet is happy and well-cared for every step of the way.

Sitter Profile Image: Alex D.
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Alex D.
Star Sitter
from
$82
per night
5.0 out of 5 stars
• 148 reviews
36 repeat clients
16 years of experience
Stratford, CT, 06614

“Alex really went above and beyond in every respect. This was the longest time away from our dogs and we were halfway around the world. It’s clear Alex really cares about animals and went out of his way to keep them entertained, loved, and exercised. He gave us frequent updates with pictures and videos giving us great peace of mind. While we were away he had to contend with the unprecedented East Coast blizzard and cold ensuring that the house was protected and the dogs were safely handed off to a sitter that took over once the storm passed. He even stayed an unplanned extra night until the roads were passable. Will use him again without hesitation and really appreciate how much he cares.”

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Sheila & John K.
Sitter Profile Image: Tiana R.
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Tiana R.
from
$65
per night
1 repeat client
10 years of experience
Poughkeepsie, NY, 12601

About: Aside from growing up caring for animals, I’ve worked at a dog daycare for about a year. During my time there I learned a lot about dog behavior and how to read their body language. Now, I am currently studying canine training and management at SUNY Cobleskill where I work with a variety of canine’s daily. So I am currently on summer break from school, so I can assure you I have plenty of time to care for your fur babies! I start my day off by making sure my babies are fed and have fresh water, followed by going out for a walk and playing outside for a little! I have a dog and a cat who is very shy. If needed I have a crate that can be used.

Sitter Profile Image: Alina S.
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Alina S.
from
$45
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
6 years of experience
Hopewell Junction, NY, 12533

“5 stars!! Thank you Alina for taking care of our French Bulldog, Cooper. Alina provided lots of updates with photos and videos, was super flexible, and I could tell Cooper was having a great time - I think he has a new best friend. We are normally quite anxious about leaving Coops but we felt totally relaxed knowing he was in great hands. Not only this but Alina left the apartment immaculate which was lovely to return home to after travelling. We will certainly be asking Alina to look after Coopie again. Thank you!”

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Ashley B.
Sitter Profile Image: Karla R.
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Karla R.
from
$110
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
11 years of experience
Kingston, NY, 12401

“Took really great care of our dog & our family’s dogs. 3 dogs for 1 person can be a lot, so thank you for helping us out and following our requests!!”

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Shailaja I.
Sitter Profile Image: Phoebe L.
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Phoebe L.
from
$45
per night
1.0 out of 5 stars
• 2 reviews
5 years of experience
Newburgh, NY, 12550

About: I’ve had dogs all my life and currently have three dogs at my parents house that I care for regularely when my parents need me to and I love it. I’ll come with treats and if your dog has any dietary restrictiond please let me know :) I’m currently working for Arc Midhudson on thurs-Sun at the moment! Sometimes there is variation in that schedule but that it for the most part :) I have a medical condition that may make me have to re schedule appointments but hopefully we can work together on it !! I could teach your dogs some basic tricks like sit and I am a good leash handler. I carry around a fanny pack with my dog stuff in it so it’s hands free and accessible for me.

Sitter Profile Image: Paul R.
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Paul R.
from
$100
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
Shelton, CT, 06484

About: I cannot imagine life without pets! I am a very loving and friendly person with a passion for animals. I provide the following services: dog walking, potty breaks, drop-in visits, overnight care & baths. I am extremely responsible and will provide the best care for your pets, guaranteed. If you have any questions, don’t hesitate to ask! I have open availability 7 days a week. I am fully committed to providing care to your pets. Please let me know the day(s), time & service that is ideal for you. I have 2 mini golden doodles and 2 cats. They are extremely friendly and get along great with other animals. While staying over or going to a clients home, I will ensure to follow the provided instructions and keep their home as clean as when I initially get there.

Sitter Profile Image: Carol K.
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Carol K.
Star Sitter
from
$95
per night
5.0 out of 5 stars
• 128 reviews
43 repeat clients
15 years of experience
West Hartford, CT, 06117

“Carol did a great job of giving Archie fun walks, sending us photos of him, and calming him during the dreaded 4th of July fireworks. Archie loves her. We're grateful!”

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Cynthia & Shad G.
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The median cost per night for house sitting in Wingdale is $70

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  • 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

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  • 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.

How to book house sitting

  1. 1. Search

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

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

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Popular requests for house sitting - Wingdale

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Sitters in Wingdale average 3
repeat house sitting clients

FAQs for House Sitting - Wingdale

Frequently asked questions about Rover

The average cost of House Sitting in Wingdale is $56 per night as of October 2026. Most bookings cost between $44 and $78 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 1,109 sitters on Rover offering House Sitting across Wingdale. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Wingdale walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Wingdale maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

<b>Tip:</b> Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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.

Yes, you can find sitters who have experience with handling special pet needs in Wingdale. On Rover:

  • 91% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 97% 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.

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