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Top rated Winstead house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I highly recommend Amber for any dog sitting or dog walking needs, no matter the size or personality of your pup! I have a 110 lb lab mix and a 70 lb Great Pyrenees mix—both can be a handful at times—but Amber handled them with confidence and care. Her experience with larger breeds (including her own huskies) gave me peace of mind from the start. What truly impressed me was how she connected with my younger dog, who is very skittish and slow to warm up to new people. By the end of the week, not only had my pup warmed up to Amber—she was jumping on the bed and cuddling next to her, something she rarely even does with me or my husband. I was amazed! Amber also sent me photos of the dogs every day to keep me updated, which I really appreciated—it helped so much when I was missing them while away. Amber went above and beyond to make our dogs feel safe and loved while we were away. We’ll absolutely be booking with her again for future stays!”

“We have used Alaska several times for our Saint Bernard Margo and Margo always seems to enjoy her visits! Alaska is friendly, communicative, and attentive. She lets us know if Margo's been having a good day, or if something was off. She's exactly what you want if you're looking for someone you can trust on Rover.”

“We couldn’t be happier with the care our three dogs received! From the moment we left, she kept us updated with regular messages and adorable photos that gave us total peace of mind. It was so clear she treated them not just as clients, but as her own — they were loved, comfortable, and happy the entire time. We will absolutely be booking again and highly recommend her to anyone looking for a sitter who truly goes above and beyond!”

“Sophia did a great job and accepted my booking very last minute. My dogs loved her and she was very professional. I'd highly recommend her services as she is trustworthy and very accommodating. Happy to see college students with a passion for animals on this app.”

About: I don’t just watch dogs—I get to know them. Whether it’s helping puppies learn the ropes or giving senior pups slow, cozy care, I tailor every visit to what your dog actually needs. I’m patient, upbeat, and love turning training moments into fun games. I pay close attention to each dog’s unique needs, energy level, and personality—because great care isn’t one-size-fits-all. And yes, I’m the sitter who celebrates every tail wag like it’s an achievement. Pet care fits naturally into my routine. I work full time Monday–Friday from 8–4, but I’m available for morning, evening, and weekend visits. I also have holidays and summers off, which gives me plenty of flexible time for daytime walks, drop-ins, and longer stays when needed. Safety and comfort are always my top priorities. I maintain a safe, structured environment by following your pet’s routine exactly as you outline it. In your home, I respect your space, secure doors and gates, and keep all food, treats, and cleaning supplies out of reach. I monitor pets closely during walks and use sturdy leashes and proper equipment. Communication is key, so I provide regular updates and photos to give you peace of mind.
About: I’ve taken care of dogs and cats my whole life and I love to play with them and take them to the park and play fetch and run with them and have them happy. My schedule is available everyday through Monday - Friday. also I don’t work so my schedule is very flexible and weekends I’m off for babysitting dogs and cat because I’m spending time with my family. I’ll be happy to be your dog sitter or cat sitter and you enjoy your day! I would baby sit them in there own environment so they feel safe around me while I pet sit for the customers and have the customers feel safe to
About: I often volunteer at the SPCA to spend more time with animals. I love animals, and it is a great take away to spend time with a furry friend amidst all of life’s chaos. I currently work a day job semi full time, but I make sure to plan around with my rover schedule! My two pets are my world, and I have fit my home schedule surrounding caring for them. I prefer to lounge around with furry babies! I have grown up with pets my entire life, and know how important it is to give them a great quality of life. I will make sure all the pets needs are met, and have a primary focus of communication with owners. I want all of my clients to feel comfortable with my service, and to enjoy their time away knowing their babies are being loved!

About: I’ve grown up with pets! My mom has even owned 3 deer. She currently has 3 dogs and 2 cats. I’ve always loved animals and will do whatever it takes to make sure you and your pet are comfortable I currently work full time as a manger, however my hours are 8-4 and I usually get out earlier. I will be there throughout the night/ early mornings to do whatever is needed. My pets are fed 3 times a day and have open water to drink throughout the day. My mom has 14 acres and they free roam. However if I’m watching someone else’s pet that will not happen and they will be leashed.
“Lexi did a great job with my boys. They were healthy and happy upon my return. She provided updates when possible since I had limited cell service. I have already booked a second visit.”

About: I’ve taken care of many dogs of all ages and sizes since I was young and none have given me any trouble. I don’t mind picking up messes that any dog might make. I absolutely love playing with them and taking them on walks. I doordash as my job so my availability is 100% open to any kind of needs your dog has. I pick what hours I work with door dash but normally I’ll door dash throughout the day then come home for the day around 5. Although when watching any animal I tend to switch up my hours so I can make sure your pup is getting all the love and attention it needs. I like to keep a clean house so no dog has a chance to get into anything that could harm them or chew on anything not wanted.
“Adeline was wonderful! She provided excellent care for my dog while I was away. She also sent me a lot of updates and lovely photos. My dog was happy and calm when I came back, and my house was in excellent condition. I highly recommend her services. She did a fantastic job!”


About: My big sister was a Dalmatian my mom had before I was even born. My first cat was at age 3. Since birth I have been around and cared for many different types of animals. They range from the dogs and cats in my family, my grandparents horses, to the various small, furry, AND scaly critters I've kept over the years. Currently have a dog, cats, fish/shrimp, a frog, a snake, and geckos! Let my love and encyclopedia of animal knowledge be used to your advantage! Currently work through the week at 11am and am usually home by 8pm. Off Sunday and Monday, so weekends are perfect! Willing to do walks in the evenings and morning check-ins throughout the week. Large yard, not fenced, walking distance to dog park. Clean,respectful, and trustworthy when in other's homes. One dog and 3 cats coexisting happily at home. Experienced with caged animals and reptiles/amphibians as well.
“Alyssa is an exceptional dog sitter and exceeded my expectations. My German Shepherd, Ava, is highly independent and energetic with borderline diva tendencies. Alyssa had my girl for a week while I was hiking in the Black Hills. From her pics and communication, I could see that Ava was in good hands. Alyssa treated my Ava and my home as if it was her own—I’m so glad I found her! I will continue to use Alyssa and recommend her highly.”

“Jennifer watched our 3 dogs during a weekend away and I couldn’t have asked for a better dogsitter. She sent pics throughout the weekend and we could tell our dogs were getting all the love we give them!! Thank you”

About: I am a former elementary teacher of twenty years, current remote worker and mom of two kids. First and foremost, I respect your privacy and will be a trusted guest in your home. Our pets are our children. I understand the stress your absence can leave on you AND your pet. I am here for you! I have provided pet sitting services for ten years. Your pet will be given a reliable, trustworthy, compassionate buddy to keep them company. I will be in consistent communication with you, providing photos and updates for added assurance. I will spend 1:1 time with your pet. They will be spoken to and snuggled throughout the day. I will follow all special requests and strive to keep you pet comfortable and happy while in my care. I work remotely. My schedule offers flexibility. Proper communication with new clients to learn about the pet's individual needs can help determine how pet care can fit in my daily routine. I am waiting to meet your fluffy family member today! I will meet all requests and routines. I will stay attentive to your pet at all times. I am a professional and will meet my contractual expectations. I will not bring other animals or humans into your private space and maintain confidentiality during our work relationship.
About: I’ve taken care of my own dog since we got her 8 years ago. I’ve pet sat for many friends with dogs as small as miniature poodles to as big as labs. I can currently dog walk or pet sit anytime during week days. I am available during weekends for walking or pet sitting but overnight sitting needs to be scheduled in advance. :) I can do anything a client needs me to do in their home. This includes letting the pets outside, feeding them, playing with them, cleaning, etc. I do not offer to care for pets in my own home.
“We have had Bessie watch our dog, Margo, several times and she has always done a phenomenal job. Bessie always takes care of Margo's fundamentals, and also make sure she has a great time with walks and play time. I think Margo seems genuinely happy when Bessie watches her. Sometimes, when using Rover, you know you come home and there's like a feeling that your dog was stressed. We have never had that feeling with Bessie. Always come home to a very happy dog!”

About: I have hands-on experience caring for pets of all kinds, from energetic puppies to senior dogs and cats with special needs. I’ve worked with plenty of families and multiple dog kennels over the years and I am now enrolled in school to become a vet. I currently work in a veterinary clinic where I have the privilege of caring for all different breeds of animals. I am trained in administering medication and supplements of all kinds as well as giving love and care to all animals with their own personalities and routines! I offer a flexible and reliable schedule that allows me to fit pet care into my routine. I plan my day around each clients needs, ensuring your babies receive consistent attention, timely visits, and dependable care every time. I make it a priority to be available when your pet needs me most! Caring for pets in their own home allows me to crate a safe, familiar, and stress free experience tailored to their needs. I take the time to build trust with both you and your pet by following routines closely, maintaining a clean environment, and providing attentive care at all times. I also keep you connected with daily photo and video updates, so you always know how your pet is doing. To go the extra mile I offer a complimentary bath with select services, so you get to come home to a clean, refreshed, and happy animal!
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 Winstead is $45
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 Winstead 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 Winstead on Rover as of Jun 2026 was about $45 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 148 house sitters in Winstead. 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, 86% of Winstead house sitters respond in under an hour.
House sitters in Winstead have an average of 17 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 Winstead.
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. Winstead 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.


