House Sitting in New Windsor
Find a loving house sitter to watch over your pets and your home.

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Top rated New Windsor house sitters
“She was fantastic! We have 2 cats and 2 dogs. She pet sat at our house when I needed to fly to Florida last minute for a family emergency. Colleen, sent us updates with pictures. Gave me such a peace of mind while gone to know my fur babies were in good hands!”


“Jacquelin was such a WONDERFUL pet sitter to my Italian Greyhound, Oliver. I've never used Rover before, and she kept my mind at ease while I was out of town for a wedding. I wouldn't have been able to go without her help! I received updates, pictures, and videos everyday. Thank you Jacquelin for being the best!”


About: I grew up on a farm and have been around animals my entire life. Cats are my favorite and I’ve had them since I was a child. In the past I have been mostly cat sitting. More recently, I have been dog walking and sitting for friend’s dogs while they are away on vacation or at work. I enjoy it as a therapeutic way of bonding with the animals as a form of self-care and mutual support and pet care co-regulation. Unfortunately, I cannot have dogs at my residence as per my lease agreement and being able to sit and walk with dogs is a way of being able to enjoy access to them without being able to own them myself. I’m looking to expand my reach and explore more breeds at this time. Specifically, I have experience with Labradors and Boxers. I’m currently working part-time and have ample time to schedule walking and feedings, and am able to stay for extended periods of time with your pets. I have two cats whom I adore and dote on at my home and I am very attentive to their needs and make sure they have an enriched environment with toys and play time, as well as grooming care.
“Preston watched my 2.5 year old sheepadoodle Archie for just under 2 weeks while I was traveling. I highly recommend Preston to anyone who needs a house sitter. He was great with Archie and provided me updates as needed and was easy to get a hold of. He even began training Archie on some different skills. He even left my house cleaner than when I left it. Preston was a great choice for house sitting and I will definitely try to use him again if I ever need someone to watch my pup and house!”

“Thomas was terrible! JUST KIDDING! I just want to keep him only for when I need him!😁 I couldn’t ask for anything more. He initially responded quickly. Showed up when we planned. He kept in touch with me. Sent pictures of my dogs when he was with them and left my house tidy. TJ, thank you again!”

“Emily was super excited to stay with my pups even with their quirks and was able to book within a week of my vacation and meet them when I had a last minute cancelation with someone else! She was very responsive both before and during my trip and kept me updated about my dogs with pictures which was super appreciated! She was also able to give medication to one of them as needed and follow the food directions as well as made time to sit with one of them who will only eat with company. I will definitely be reaching out to her again in the future!”

“Jasmine was awesome! She kept us updated on how our dogs were doing and sent great photos. She was professional and left my house as she found it. Definitely going to book her again!”


“Jack was terrific with Imo; kept us updated and sent pics for the three days we were away. We returned home to a calm dog, excited to see us. Will definitely call on Jack again.”

“Abbey was great with our senior guy for a week while we were on vacation. She sent us pictures and updates twice a week and follow all of our instructions for him. We will use Abbey again!”
“Anel was WONDERFUL staying with our very 'discerning' dog! She's got great, calm, loving energy that put him at ease immediately, and is very professional. So glad to know she's nearby and definitely re-booking soon!”

“Melissa was amazing! Our cat has been really picky with food and Melissa went out of her way to try different options to make sure she ate. When we came home, we honestly think our cat was disappointed it was us and not Melissa, lol. The house was in beautiful shape, and we never once felt nervous about being away from home. THANK YOU!!”
“Thu was amazing. I had another sitter booked who canceled on me on Thanksgiving morning! Thu saved the day! She spent lots of time loving my babies and sent me pictures. I would highly recommend her.”

“No worries your dog is with a superstar! He was accommodating and loving towards our very senior Maltese and he also took time to reach out and update. Hes great with my lab too!!! He is fantastic! Highly would recommend and rebook. Very caring individual”

About: Hi. My name is Kiki and I love dogs!! I have years of hands-on experience working with dogs of all breeds, sizes, and temperaments. I was a manager at a cage-free dog daycare for 5 years, where I handled everything from group play supervision to administering medications and managing daily care routines. I also volunteered for 3 years at Second Chance Dog Rescue, helping with socialization, walking, and basic training. In addition, I’ve provided trusted pet sitting services in Peekskill, NY for 5 years until the family relocated. I’m trained in pet CPR, comfortable administering all types of medications, and have a dog of my own—so I truly understand how important it is to find someone reliable and compassionate to care for your pets. I have a car, am highly dependable, and treat every animal as if they were my own. Although I work full-time and attend school, I have large daily time blocks available between commitments, which I dedicate to pet sitting, walking, and drop-in visits I care for every pet like my own, ensuring they feel safe, loved, and comfortable while following their regular routine, my skills are administering medications, and giving personalized attention. Every pet has a specific personality so I try to respect that much like people.
“Wonderful!! Katie is so kind and has the calmest demeanor. As soon as we did a meet and greet I felt so comfortable leaning my dog Sophie in her care. Katie provided photos and in depth updates so I had nothing to worry about! Great communicator and do easy to work with. Would highly recommend and we will definitely be using her again!”

About: I worked in the animal industry for the last six years and have been a certified Dog Trainer for the last five. I have experience with senior dogs; Medication and specific dietary needs. I have two for babies at my own. Being a pet owner and working in the animal industry, I understand how nerve-racking it is to trust somebody with your pets care. I’m looking to create peace of mind. Monday through Friday early morning and late evening. Saturday 9AM to 12PM I’m absolutely willing to create more of a flexible schedule upon request with ample notice. Currently in an apartment with a medium to large dog and a cat. Not currently offering boarding in Connecticut. The house in New York has a 6 foot fence with large amount of yard space.
Over 102 pet parents in New Windsor have booked house sitting
New Windsor pet parents share their Rover experiences
Preston was absolutely amazing with Bruno! Bruno can definitely be a handful, but Preston handled him with patience, care, and professionalism every step of the way. He went above and beyond by taking Bruno on walks, keeping him engaged, and even helped teach him how to use his communication buttons. I can tell Bruno was taken well cared of and genuinely enjoyed his time with Preston. The updates gave me peace of mind, and I came home to my happy sweet baby angel. I highly recommend Preston to anyone looking for someone who will treat their pet like family! 💜💜💜

Emily was super excited to stay with my pups even with their quirks and was able to book within a week of my vacation and meet them when I had a last minute cancelation with someone else! She was very responsive both before and during my trip and kept me updated about my dogs with pictures which was super appreciated! She was also able to give medication to one of them as needed and follow the food directions as well as made time to sit with one of them who will only eat with company. I will definitely be reaching out to her again in the future!

Jonathan provided excellent care to my two senior dogs. One of them is a diabetic and blind and requires adhering to a strict feeding and medicine schedule. Jonathan followed the schedule and my dog was very healthy and happy when I returned home. I received daily updates and photos so that I could see how both of my dogs were doing. His consistent communication and care made it so much easier to travel away from home. I would definitely rebook!
I knew the minute I saw Sam with my pup that I could go away & that all would be well. She did a week of housesitting with my golden retriever. Sam is sweet, personable & very capable. I got texts & pics and few times a day. They went for walks when it wasn't too hot, played and did lots of snuggle time. Thanks again for everything, Sam! ❤️
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 New Windsor 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 New Windsor 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 New Windsor on Rover as of Jun 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 Jun 2026, there are 773 house sitters in New Windsor. 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 New Windsor house sitters respond in under an hour.
House sitters in New Windsor 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 New Windsor.
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. New Windsor 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.







