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

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Top rated Winfield Woods house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Jenny was kind, caring, punctual and a great communicator. She took wonderful care of our sweet puppy while we were away. Jenny also took great care of our home, even getting the mail I forgot to put on hold. Her communication by text both before and during our time away was speedy and she even included photos of our pup having fun. We look forward to Jenny caring for our pup the next time we are away.”

“Jolene was beyond amazing. We had something come up and our original plans for our boys got cancelled. She was available last minute, was very responsive, and she is extremely polite. She kept me updated with photos and videos. She loved on our boys like they were how own! I am definitely a crazy dog mom and she put me at complete ease! We will definitely use her again!”

“If you’re looking for a great pet/house sitter, Riley is your person. Riley took great care of my pup and fish, checked in daily with me, sent photos and provided daily walks each day. At the end of the stay, Riley summarized Toby’s week, including highlights and household things she did on a sheet of paper. Riley is very reliable and I’ll definitely book her again in the future.”

“Lora went above and beyond caring for my dog Brinkley. He has tons of play time which he loves, and I have so amazing photos and videos. She cared for him as she would her own dog. She went above and beyond when my flight was delayed to care for him and alleviated all of my worries during an exhausting time.”

“Hailey did a great job!! We came home to our dogs looking happy and well and the house looked great after a nearly 2 week vacation. She sent very cute pics on request, and checked in daily. ?”

“Sarah took our booking the week of and still made time to come do a meet and greet with us beforehand! She was very polite and took great care of our pets and home. I’m very pleased and would absolutely book her again.”

“I have a Rottweiler and anyone with a big dog knows how hard it is to find a sitter. Kerri does an amazing job with him. She is an incredible house guest. I appreciate the love she has for my buddy. Knowing he is with someone that loves him allows me to enjoy my vacations, worry free.”

“Hannah took such great care of our 2 sr pups. She communicated regularly when our bulldog's allergies flared up. Our dogs were happy and content when we got home. The house was also nice and tidy.”

“Virginia took care of our cat snd home while we were away for a week. She kept us updated about our kitty with daily photos and messages. She left the house tidy. We are very pleased with Virginia and will ask her to care for our cat and home in the future.”

About: I am currently a College Student majoring in Animal Behavior. I have two years of experience pet sitting and walking dogs. I’ve cared for dogs ranging from puppies to seniors. I have a four year old Black Lab (Olive), and a three year old Boxer (Kyla). Can’t wait to meet your furry friend(s)! I have morning classes, so I have afternoons, evenings and weekends to take care of your pups. During school breaks I will be more available for your needs. I take dogs on leashed walks fitting their needs. I also keep them entertained and fed inside when/if needed. I also can play with your dog in a fenced yard.

About: I’ve been around dogs my whole life and currently have two pugs of my own, so I understand how important it is to find someone you truly trust with your pets. I’m patient, dependable, and attentive to each dog’s personality and routine. I’m comfortable with walks, feeding schedules, medications, senior dogs, and giving pets extra attention and affection while their owners are away. I also work in hospice care, so being compassionate, calm, and reliable comes naturally to me. I’ll treat your pets like family and make sure you feel updated and reassured while you’re gone. I work full time during the week from 9am–6:30pm, but pet care fits naturally into my routine since I already care for my two pugs daily. I’m available for evening visits/walks on weekdays and have much more flexibility on weekends for drop-ins, walks, and overnight care. I’m reliable, communicative, and committed to making sure pets feel comfortable, cared for, and loved while their owners are away. Your pet’s safety and comfort are always my priority. I pay close attention during walks and outdoor time, especially in hot weather, and I never leave dogs outside longer than they should be. I make sure pets always have fresh water, a clean environment, and close supervision to keep them safe from anything that could bother or harm them. I’m also very mindful about keeping floors and spaces clear of anything pets could get into or accidentally swallow. I understand how important trust is when someone is caring for your animals, and I’ll always treat your pets with the same care and attention I’d want for my own
“Thanks for taking care of my babies! I’m so glad to have someone that they were comfortable with so quickly. We appreciate that you were considerate of our home and so sweet with our girls.”

About: I’ve cared for family and friends’ pets of all shapes and sizes throughout high school and college. Whether it was my college friend’s energetic puppy or my aunt’s elderly cat, I always loved spending time with them. I offer walks, feedings, playtime, possible vet trips if needed, and of course quality time with your pet in the comfort of their own home where they feel safest and happiest. Currently home for the summer which is perfect for open availability whenever and wherever. Available mornings, evenings and nights! I am flexible in almost every booking if needed. Pets are free to roam throughout the house! Dogs would have to be on a leash to be outside due to the unfortunate circumstances of having no fence in my back yard.
About: I have always had dogs and cats growing up, which peaked my interest in animal care. In high school I worked as a kennel technician at a boarding kennel and gained an internship at the local veterinary office. now in college, I am studying animal science to hopefully get a degree in veterinary medicine, and continue to pet sit for my friends and family including both cats and dogs. I'm currently home from college for the summer, and home most of the time! I do have a car, and am available almost any time of the day. I have pets in my home that are not socialized, so I would not be able to pet sit in my own home, but I am happy to make the trip to the comfort of their own home.
About: I have 15 years experience working as a veterinary technician at cat and dog hospitals. I will care for your pet as if they were my own. I can administer medication and assist with mobility, if necessary. I can board at my home, or care for your pet in your home. Thank you so much for taking the time to read my profile. I look forward to meeting you! I work from home in Mount Airy, MD. My schedule is very flexible and open. I can assist your pet week days, week nights, and weekends! I have a small house with a big yard (no fence. I will need a leash). I live with my lovely ten year old daughter who is also an animal lover and very gentle. I also have an indoor/outdoor cat that can be separated to a different floor, if necessary, and they will never meet. If my living situation is not ideal for your pet, I am more than happy to make visits or stay at your home to care for your pet’s needs!

“Kelsey did a great job taking care of our dogs at our house while we were away for a weekend. She kept us updated with pictures and notes, and was really good at communicating with us about what we expected. We came home to happy dogs and a clean house - I couldn't ask for more!”
About: I have had dogs since I was 5, and I started working at a doggy daycare when I was 18. My senior year of highschool I was an intern at a local animal hospital and I loved it! I would love to spend the summer with your dogs and provide whatever services and help you may need! I am currently unemployed for the summer, so I can spend any time needed with your dogs. I have applied for jobs, so if my availability changes you will be notified but as of right now I am free to do anything. I have a huge (not fenced in) backyard. Since working at the doggy daycare, I have experience in helping dogs into crates, doing specific food for the dogs, attending to their personal needs, and making sure they have hours of entertainment and love.
About: Hi! I’m Victoria , a dedicated dog lover with 10+ years of experience caring for dogs of all sizes, ages, and temperaments. Whether your pup loves energetic playtime, calm cuddles, or structured routines, I’m here to make sure they feel safe, loved, and happy while you’re away. I am currently a stay at home mom for seven dogs of my own, I have plenty of time on my hand to take care of your animals whenever you need me to stop by. I would take care of your pets, as I would take care of mine, I treat your pets like I treat mine, they are important to me. I care about them very much, and I would never let anything happen to them.
Winfield Woods pet parents share their Rover experiences
Hailey recently watched our three dogs and two cats while we were out of town. She took such good care of them and was in constant contact with us, going above and beyond to care for our physically disabled cat. I truly felt like she cared for our animals as if they were her own. Knowing that she could handle everything, we were able to relax completely on our vacation. We always felt connected and knew our pets were safe and happy. If you are looking for a pet sitter who is reliable, responsible, and genuinely compassionate—especially if you have a multi-pet household or pets with special needs—I cannot recommend Hailey highly enough!

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 Winfield Woods is $50
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 Winfield Woods average 4 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 Winfield Woods on Rover as of Jun 2026 was about $50 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 2,396 house sitters in Winfield Woods. 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, 85% of Winfield Woods house sitters respond in under an hour.
House sitters in Winfield Woods have an average of 14 years of experience. House sitters with repeat customers have an average of 4 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 Winfield Woods.
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. Winfield Woods 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.




