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

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated New Windsor house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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!”

“If I could give Rebecca more than five stars, I would! From the moment she walked in and greeted our pups, we knew they would be in good hands and we did not have to worry while we were attending a family wedding. Her skills at handling two puppies was nothing short of impressive. Her communication and people skills also made her a standout. She was super pleasant from the get go and made our first experience with Rover was wonderful! Thank you Rebecca!”

“Jessie is simply the BEST PET SITTER EVER. Our pup, Miss Susie is shy, but remembered Jessie and asked for “belly rubs” immediately. That made us feel less guilty and more secure as we departed. Jess sent us photos each day, and she even got Susie to sit with her on a pad outside - this can be a challenge. Now if you can believe this, Jessie not only laundered her own sheets, but the other set of guest room sheets so I would not be confused on which ones were clean. My best friends are not that considerate. This woman is a Saint! My only reservation in doing this review, is too many others will hire her and she won’t be available for us . . . 😎”

“Nicole was fantastic! Our dog Juniper loved having her spend a night with her. I felt very comfortable having her in our home and taking care of our girl. When she had to leave while we were in our way home, she was sure to leave the TV on for our dog, it was a great touch of care. We know she listened to the little details we spoke about during our introduction. We will definitely be using Nicole again!”

“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!”

“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!”

“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.”

“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!”

“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”


“Jacquelin took such good care of our dog, Ollie while we were away. She made sure to send us frequent updates and texts. She clearly has a knack for making pups feel at ease and we would highly recommend her to anyone looking for a dog sitter/walker.”

About: I’ve been pet sitting for about 10 years and have experience with all kinds of pets, from large dogs like German Shepherds to small terriers, cats, kittens, and even fish. I’ve cared for energetic, shy, and senior pets, including those with specific diets or unique needs. I’m very adaptable, patient, and genuinely love animals, so I’ll always make sure your pet feels safe, happy, and well cared for. I’m a college student, so my schedule is pretty consistent during the week. My busiest days are Tuesdays (8 AM–4 PM) and Wednesdays (10 AM–4 PM). On Mondays and Fridays, I’m only away from 10 AM–2 PM, and Thursdays I’m gone just from 11 AM–12 PM. Outside of classes, I’m very flexible and able to give pets plenty of attention, walks, and care. I also work part-time at a country club, but it’s currently the off-season, so my schedule is mostly focused on school. In my home, pets are treated like family. I have two friendly pets of my own, so I’m very used to maintaining a safe, clean, and comfortable environment. I always make sure pets get plenty of attention, playtime, and stick to their usual routines. In a client’s home, I carefully follow all instructions and make it a priority to understand each pet’s specific needs, habits, and personality. I’m attentive to feeding schedules, walks, litter box or potty routines, and any special care instructions. If I’m ever unsure about something, I always ask to make sure I’m doing exactly what’s best for your pet. I’m very patient, reliable, and detail-oriented, and I truly care about making pets feel safe, comfortable, and loved while you’re away.

About: Hi! I’m a lifelong animal lover with many years of hands on experience caring for pets of all kinds. I’ve worked with dogs of all breeds, sizes, and ages from energetic puppies to senior dogs needing a gentler pace, as well as cats, rabbits, and other small animals. I feel deeply attuned to each animal’s unique personality and needs, and I approach every pet with patience, empathy, and genuine affection. Caring for animals is something that comes naturally to me. Friends and family consistently rely on me for regular pet sitting and care because they trust me to be attentive, responsible, and loving. I understand how important it is to feel at ease when leaving your pet with someone, and I take that responsibility seriously. I currently work in yoga and childcare, which gives me a flexible schedule and a calm, grounded presence that animals tend to respond well to. Whether your pet needs playtime, walks, overnights, or meds/extra TLC, I’m here to provide a safe and nurturing environment. I would love to meet you and your pet and support their routine while you’re away! I work here as a yoga teacher and provide child care to local families, my schedule is very flexible and moves between Beacon and Peekskill. I am happy to adhere to the routines you have created and personalize care based on your fur baby's needs. Walking, overnights, any special care ( treatments/ meds).

“Kasper is an amazing pet sitter! He was punctual, communicative, and took great care of my home and pets. He was also super caring and sensitive to noticing any little thing that may be off with my dog Goji who can get separation anxiety- even sleeping with him downstairs the first night to ease his nerves. I will def be recommending Kasper to friends and reach out again when I need care!”

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.
“Alexis was great with our pups. We got daily updates, and all of our requests were handled. We have a fear reactive pup and Alexis was even willing to come and meet our pooches several times before our actual trip to allow our pups to get comfortable (and vice versa). Alexis is chill and easy going and the doggos vibed well with that. We found Alexis to be very reliable, patient, responsible, kind, and essentially everything we could ask for in a sitter. We definitely recommend Alexis.”

Over 101 pet parents in New Windsor have booked house sitting
New Windsor pet parents share their Rover experiences
Valerie did a great job of watching after two pugs! She was so responsive and sent multiple pictures which put me at ease while I was gone. And on top of taking excellent care of my dogs when I returned, my apartment was really tidy which I appreciated! Will absolutely book with her again and would recommend her to anyone!

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!
They did an incredible job watching my babies! Extremely responsive responsible and loved on my dogs like they were their own. I got lots of updates a they were flexible with me when my trip was delayed. Extremely professionally, responsible and all around wonderful. I can’t say enough good things and will be using them again!!

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! ❤️
Lizzie was outstanding! Prompt, upbeat and enthusiastic about spending some time with our dog. She even sent some pictures, to show us our little guy, which gave us a peace of mind, while we were attending an event. If you need a sitter, while visiting Fishkill/Newburgh, CALL ELIZABETH! She’s fantastic!! 👍🏻👍🏻

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 $65
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 Apr 2026 was about $65 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 Apr 2026, there are 819 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.







