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Top rated Winslow house sitters

“Brittany did an amazing job with my dogs. This was the first time leaving them and it went very smooth. Great communication. Great experience. Definitely recommend!”


“My pups absolutely love Skye! She has watched them several times now and is always fantastic! She sends updates and pictures throughout the day. She’s great at communicating and loving on our dogs. Highly recommend!”


About: I’ve had many dogs in my life. Right now, I’m the mom of a four year old chihuahua! I love to watch dogs for people as a fun side job/hobby. While I may be new to the app, I’ve done this my entire life. You will get the quality and trustworthy care your pet deserves. Give me a chance! You will get your moneys worth. I’m currently working part time, I don’t do much except work and spend time with my own pup lol. I basically have open availability to meet your schedule’s needs. I can easily crate your dog if needed. I have two dog tents and a kennel. I have a safe, quiet apartment where your pet will feel relaxed and at home. There’s also plenty of room to run outside.

“Natalie was awesome. She came to the house and met the pups before our trip to meet them and see their routine. She kept in touch with us throughout the weekend too. The dogs were happy to have someone stay with them for the weekend. I will definitely use her again in the future.”


About: I treat each pet like my own—with patience, love, and a strong focus on their individual needs and routines. I'm reliable, communicative, and always make sure pet parents feel at ease while they're away. Whether it’s sticking to a specific feeding schedule, giving extra cuddles, or keeping you updated with photos and messages, I ensure your dog feels safe, happy, and at home. Dog sitting fits into my weekly schedule in a way that allows me to give each pet the attention and care they deserve. I work full-time during the day, so I typically take on dog sitting jobs that align well with my availability—mornings before work, evenings, and weekends. During those times, I focus fully on making sure your dog gets plenty of exercise, affection, and consistency. If your pup is comfortable with some alone time during the workday, I’m a great fit for overnight care or weekend stays. I provide a secure environment, closely supervising their activities, and following any specific care instructions from the owner. I ensure they have proper food, water, and exercise, avoid hazards like toxic plants or open gates, chocking hazards and stay alert to signs of illness or stress. Regular check-ins and maintaining up-to-date contact information also help in case of emergencies.

About: I’ve been recommended to many by word of mouth, so I decided to bring my business to Rover as well! There’s nothing I love more than being able to provide comfort for your pets whenever you’re away. Me and your pets will go on walks, play dates, and anything else they enjoy! Be prepared for lots of photos of us enjoying our days together! I am working part time while doing a summer internship. Ideally, I am available for overnight stays, whether it be for the weekend or two weeks! I also have sitter backups for any extra care needed in which I’m not able to tend to. I’m currently in graduate school at Morehead State in Ky and will resume in-person classes in the middle of August. I haven’t dog sat in my own home before because I have 2 dogs and a pig of my own. Caring for your home and pets is what is most important to me! I will always be easy to reach, whether it be by phone, text, or FaceTime! I will also water your plants, pick up your mail, take out the trash, etc.

About: I've taken care of dogs ever since I can remember. Neighbors, friends and family have relied on me to walk, feed and bathe their pets I’m available all week to take care of furry Doggy, I will take them out for walks, parks, get them to run, play with ball I have a fenced yard and two friendly dogs to keep your fur baby company, feel safe. I can easily crate your dog if needed.

About: My husband and I are animal lovers and enjoy getting to care for other people’s fur babies! We have two golden doodles who love making new friends, whether it’s for playtime at home or fun walks around the neighborhood. Our home is full of love, fun, and plenty of tail wags, and we can’t wait to welcome your pup—whether for a stay or a stroll! I work from home some days, so when I’m home, your pup will get plenty of attention, playtime, and exercise throughout the day! Even on the days I’m not home full-time, my schedule is flexible enough to accommodate most needs for walks, drop-in visits, and overnight stays. Whether your dog needs a fun playmate, regular potty breaks, or a stroll around the neighborhood, I’m here to make sure they’re well cared for! We have a spacious, fenced-in yard where your pup can safely run, play, and get their zoomies out! For added security, we also have crates available if your dog needs a safe space or if I need to step out for a short period. Our two golden doodles love making new friends and will help ensure your pup gets plenty of exercise and social time. Your dog’s safety and comfort are my top priorities, and I will always treat them like part of the family while they’re in my care!

About: Taken care of animals since I was a kid. I absolutely love animals. They need someone to stand up for them and a voice willing to protect them. I'm a Army Veteran who is looking to keep busy. Hi, im here to take care care and support your loved one. I know what it means to have an animal as part of your family. I can take care of your animal as I do with my 2 Chihuahuas , with care and love. They will be well taken care of. I'm here to provide the best care as possible

About: Hi, I’m Ellie, and I’ve been caring for animals for as long as I can remember! I’ve had dogs my whole life and truly understand how much they mean to their families. Whether it’s daily walks, playtime, or just giving them the love and attention they deserve, I’m here to make sure your pet feels happy and cared for while you’re away. As an active person, I love getting outside for walks (or runs!) and will tailor each outing to your pet’s needs. I’m also highly dependable, always arriving on time, and committed to making sure your pet is safe, comfortable, and well taken care of. I’d love the opportunity to meet you and your furry friend—let’s connect! As a first-year graduate student, my days are filled with studying and classes, but I always make time for what I love—caring for animals! My schedule is flexible throughout the week, making it easy for me to fit in walks, drop-in visits, or pet-sitting based on your needs. While weekends are usually reserved for studying or travel, my availability can vary depending on the week—so don’t hesitate to reach out! I’d love to see how I can help take care of your pet while fitting seamlessly into both of our schedules. When caring for pets in a client’s home, I provide personalized attention, including playtime, walks (or runs, if your pet enjoys them!), feeding, and plenty of love. Whether they need a high-energy outing or a relaxed visit, I tailor my care to their unique needs. If you're interested in a specific type of care, feel free to reach out :)

About: Hi! My name is Hadyn (23yo) and I can’t wait to meet your furry family! After being a loyal pet sitter to very few for the better half of a decade, I’m looking to expand my clientele! I am currently available for house sitting, drop-in visits, and dog walking. I have always been surrounded by animals, and found them to be great company! These days my furry family includes 3 cats and 3 ferrets, along with my parents’ 3 dogs, cat, and snake (scaley fam). Due to this and my own personal passion, I have a wide variety of experience with dogs, cats, and small animals. I’ve worked with many different types of dogs and cats including seniors and those with special needs. I appreciate any specific and thorough instructions for how I can best support your pet. I also have experience administering oral medication. For the consideration of larger dogs, I must say I can only lift up to 50lbs. I strive for a holistic approach to an animal’s individual wellness emphasizing play (exercise & enrichment activities), a stress-free & loving environment, and nutrition. Though I am not a vet, I can offer advice based on my own knowledge and experiences working with pets in a personal and professional setting. For overnight stays in your home, upon request I can water plants, bring in mail, & take out the trash. I will be easily reachable by text or call, whichever you prefer, and will happily provide picture updates! Thank you for reading and I hope to hear from you! :) I have pretty open availability! If I take an overnight visit, I will routinely check in on my own animals 2-3 times per day depending. 30 min visits at a time is all I need! I live in Catlettsburg, so wherever you are in the Tri-State shouldn’t be far! I offer dog walking, drop-ins and house sitting! This is for the comfort of my own cats. You can breathe easy knowing that I will do all I can to ensure a fun filled, comfortable, and safe experience for your pet. They will get a balance of playtime and love, all while following the feeding routines you’ve set for them! Additional instruction is encouraged to make sure they get everything they need & for any ground rules set in the home.

“Brooke is an amazing pet sitter. She took great care of my crew while we were overseas. We got regular updates and pictures, medications were given correctly and without issue. When one of my dogs got sick near the end of the trip, she communicated well with me and helped coordinate to get her the care she needed. I would definitely recommend her to anyone!”


“Brooke is very professional and for being a stranger staying in our home it was quite easy to trust her. We have a seriously high energy doodle and an eight month old beagle mix and she did great with them. Her photos of the pets were a nice touch. I would recommend her to anyone.”


“We feel at ease and never worry when Shaea stays with Lila. We always come home to a clean home, just as we left it. Lila is always her happy self when we get home PLUS she gets all excited to see Shaea when she comes over.”


About: As someone who has owned dogs, cats, bunnies, pigs, an axolotl, a monkey (yes a monkey); I feel well versed and confident in my abilities to give your pet all the love and care it desires. From baby stage to old age, I am willing and capable. I am a PE teacher who looks forward to sharing love for exercise with your pet! This is how I leisurely stay active and moving after work hours and during summer break. During the months of June and July, I am offering open availability to reach the needs of as many pets as possible. Whilst the school year is in session, August-May, availability moves to evenings through the week, and open availability on the weekends. In your home, I respect your space and follow your pet’s routine. I make sure your furry friend feels safe, and gets plenty of attention. From daily walks and playtime to meal prep and snuggles, I provide consistent, loving care while keeping your home tidy and secure. In my home, I provide a safe, cozy, and pet-friendly space where they can relax, play, and feel right at home. I stick closely to your pet’s routine, including feeding schedules, potty breaks, walks, and medication if needed. Whether they’re high-energy or more laid-back, I tailor the day to their needs—with lots of playtime, cuddles, and supervision throughout. I have a large fenced in backyard that leaves lots of room for zoomies and playtime. I never leave pets unattended for long periods, and I make sure they’re always comfortable, entertained, and loved. I have a very playful Dachshund who looks forwards to play dates :) I’ll also send regular updates and photos so you can relax knowing your pet is happy and in good hands. As someone who desires to give back to the community in a variety of ways, I can assure you, your pet is in good hands.

About: I’ve taken care of my household dogs for 18 years. Sadly due to my father’s allergies I haven’t been able to have a cat. But have been around them in any chance I can get and have experience caring for them. I’m working part time but would love to make room for taking care of your pets. I also volunteer at St Mary’s but will do my best to fit your animal into my schedule. I can’t care for pets in my own home due to my family not wanting to be around pets at the moment. But I would love to branch out to other homes to care for your pets.

About: Hi, my name is Shelley Upchurch and I am 56 years old. I am originally from Huntington but spent several years in Florida and Virginia. I recently decided to try doing something I love which is taking care of animals. I know first hand how hard it is to find honest , reliable, and loving care for your pets. I have had pets my whole life and have fostered animals for several local rescue groups and also for groups in Florida. I have been actively involved with rescue for years. When I was growing up, my dad had a farm with horses, goats, donkeys and sheep so I have experience with several types of animals. I currently have 3 dogs and two cats of my own. I can provide personal and professional references along with vet references if needed. If you are ready for someone you can trust and depend on to care for your furbabies like they are their own then please request me. I look forward to meeting your furbabies and spending time with them. I am flexible with my schedule as this is going to be my only job right now so I can work with you on your scheduling needs. During my time with your babies, I will provide you with pictures and regular updates. I will love your furbabies in your absence like I would my own and provide them with the best care possible all while following your specific instructions.

About: Over the years, I have built a reputation as a reliable and caring dog walker and pet sitter, looking after both small and big dogs for multiple friends and neighbors. My experience spans various breeds and temperaments, ensuring that each pet receives personalized attention and care. Whether it's a quick walk around the block or extended pet sitting services, I provide peace of mind to pet owners, knowing their furry friends are in good hands! As a nursing student and extern, I maintain a flexible schedule that allows me to accommodate any pet parent's needs with proper notice. Pet care is an integral part of my daily routine, and I take pride in being able to balance my responsibilities while providing exceptional care for your furry friends. My reliability and dedication ensure that your pets receive the attention and love they need, no matter how busy life gets! When taking care of a client's pet in their home, I make sure to follow their rules and wishes to the letter. I understand that every pet has its own routine and preferences, and I am committed to maintaining that consistency. From feeding schedules and walking routines to playtime and specific care instructions, I ensure your pet feels comfortable and secure while you're away. Your peace of mind is my top priority, knowing your furry friend is in familiar surroundings and well cared for.
Loving house sitters in your neighborhood
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Brittany W.
Star Sitter


“Brittany did an amazing job with my dogs. This was the first time leaving them and it went very smooth. Great communication. Great experience. Definitely recommend!”


Skye K.


“My pups absolutely love Skye! She has watched them several times now and is always fantastic! She sends updates and pictures throughout the day. She’s great at communicating and loving on our dogs. Highly recommend!”


Cheyanne R.
About: I’ve had many dogs in my life. Right now, I’m the mom of a four year old chihuahua! I love to watch dogs for people as a fun side job/hobby. While I may be new to the app, I’ve done this my entire life. You will get the quality and trustworthy care your pet deserves. Give me a chance! You will get your moneys worth. I’m currently working part time, I don’t do much except work and spend time with my own pup lol. I basically have open availability to meet your schedule’s needs. I can easily crate your dog if needed. I have two dog tents and a kennel. I have a safe, quiet apartment where your pet will feel relaxed and at home. There’s also plenty of room to run outside.


Natalie H.

“Natalie was awesome. She came to the house and met the pups before our trip to meet them and see their routine. She kept in touch with us throughout the weekend too. The dogs were happy to have someone stay with them for the weekend. I will definitely use her again in the future.”


Grace G.
“We have used Grace to care for our two dogs and our home on several occasions. She kept frequent contact and gave us updates throughout the day. My dogs were happy and content when we returned. I would highly recommend Grace to care for your pets, she is a natural! .”


Regan M.
“Regan is awesome. I have 3 dogs and she house/pet sits for me when I travel. Regan has a gentle nature and loving spirit towards animals and I’m able to feel at ease knowing my babies are being treated with kindness and love. Not only is Regan intelligent and dedicated to doing a great job, she sends daily text updates with pictures and, even lets them sleep in the bed! But most importantly, all my dogs love her!”


Damien M.
About: I've taken care of dogs ever since I can remember. Neighbors, friends and family have relied on me to walk, feed and bathe their pets I’m available all week to take care of furry Doggy, I will take them out for walks, parks, get them to run, play with ball I have a fenced yard and two friendly dogs to keep your fur baby company, feel safe. I can easily crate your dog if needed.


Megan D.

“Thank you so much for your help this weekend, I greatly appreciated it!!”


Summer A.Star Sitter

“Summer is always great with both my dog and cat. She keeps me informed about what is going on and handles the day to day issues perfectly. Highly recommended!”


Josie C.Star Sitter
“Josie is one of the best pet owners and caregivers I have ever met! She loves both cats and dogs. She’s taken excellent care of my dog in the past. There’s no one else I’d rather leave or trust to leave my animals with. She does a great job!”


Bryan C.
“He is responsible and great with animals. He deserves to be a pet sitter. He has what it takes.he is gentle and loves animals.he would make a great care giver for animals.”


Ellie D.
“Ellie is a fantastic caregiver and would be any pet’s best friend. Her years of service working with young children showed a patient and loving side that all walks of life would benefit from. She loves all things that dogs love: food, running, and cuddles. Ellie is easygoing, responsible, and the ideal dogsitter.”


Hadyn K.
About: Hi! My name is Hadyn (23yo) and I can’t wait to meet your furry family! After being a loyal pet sitter to very few for the better half of a decade, I’m looking to expand my clientele! I am currently available for house sitting, drop-in visits, and dog walking. I have always been surrounded by animals, and found them to be great company! These days my furry family includes 3 cats and 3 ferrets, along with my parents’ 3 dogs, cat, and snake (scaley fam). Due to this and my own personal passion, I have a wide variety of experience with dogs, cats, and small animals. I’ve worked with many different types of dogs and cats including seniors and those with special needs. I appreciate any specific and thorough instructions for how I can best support your pet. I also have experience administering oral medication. For the consideration of larger dogs, I must say I can only lift up to 50lbs. I strive for a holistic approach to an animal’s individual wellness emphasizing play (exercise & enrichment activities), a stress-free & loving environment, and nutrition. Though I am not a vet, I can offer advice based on my own knowledge and experiences working with pets in a personal and professional setting. For overnight stays in your home, upon request I can water plants, bring in mail, & take out the trash. I will be easily reachable by text or call, whichever you prefer, and will happily provide picture updates! Thank you for reading and I hope to hear from you! :) I have pretty open availability! If I take an overnight visit, I will routinely check in on my own animals 2-3 times per day depending. 30 min visits at a time is all I need! I live in Catlettsburg, so wherever you are in the Tri-State shouldn’t be far! I offer dog walking, drop-ins and house sitting! This is for the comfort of my own cats. You can breathe easy knowing that I will do all I can to ensure a fun filled, comfortable, and safe experience for your pet. They will get a balance of playtime and love, all while following the feeding routines you’ve set for them! Additional instruction is encouraged to make sure they get everything they need & for any ground rules set in the home.


Brooke V.

“Brooke is an amazing pet sitter. She took great care of my crew while we were overseas. We got regular updates and pictures, medications were given correctly and without issue. When one of my dogs got sick near the end of the trip, she communicated well with me and helped coordinate to get her the care she needed. I would definitely recommend her to anyone!”


Brooke M.

“Brooke is very professional and for being a stranger staying in our home it was quite easy to trust her. We have a seriously high energy doodle and an eight month old beagle mix and she did great with them. Her photos of the pets were a nice touch. I would recommend her to anyone.”


Shaea S.

“We feel at ease and never worry when Shaea stays with Lila. We always come home to a clean home, just as we left it. Lila is always her happy self when we get home PLUS she gets all excited to see Shaea when she comes over.”


Tommi L.
About: As someone who has owned dogs, cats, bunnies, pigs, an axolotl, a monkey (yes a monkey); I feel well versed and confident in my abilities to give your pet all the love and care it desires. From baby stage to old age, I am willing and capable. I am a PE teacher who looks forward to sharing love for exercise with your pet! This is how I leisurely stay active and moving after work hours and during summer break. During the months of June and July, I am offering open availability to reach the needs of as many pets as possible. Whilst the school year is in session, August-May, availability moves to evenings through the week, and open availability on the weekends. In your home, I respect your space and follow your pet’s routine. I make sure your furry friend feels safe, and gets plenty of attention. From daily walks and playtime to meal prep and snuggles, I provide consistent, loving care while keeping your home tidy and secure. In my home, I provide a safe, cozy, and pet-friendly space where they can relax, play, and feel right at home. I stick closely to your pet’s routine, including feeding schedules, potty breaks, walks, and medication if needed. Whether they’re high-energy or more laid-back, I tailor the day to their needs—with lots of playtime, cuddles, and supervision throughout. I have a large fenced in backyard that leaves lots of room for zoomies and playtime. I never leave pets unattended for long periods, and I make sure they’re always comfortable, entertained, and loved. I have a very playful Dachshund who looks forwards to play dates :) I’ll also send regular updates and photos so you can relax knowing your pet is happy and in good hands. As someone who desires to give back to the community in a variety of ways, I can assure you, your pet is in good hands.


Cameron S.
About: I’ve taken care of my household dogs for 18 years. Sadly due to my father’s allergies I haven’t been able to have a cat. But have been around them in any chance I can get and have experience caring for them. I’m working part time but would love to make room for taking care of your pets. I also volunteer at St Mary’s but will do my best to fit your animal into my schedule. I can’t care for pets in my own home due to my family not wanting to be around pets at the moment. But I would love to branch out to other homes to care for your pets.


Shelley U.
“Shelley has watched my 4 fur babies (ages 2-12 yrs 38-75 lbs) twice and both times was very attentive and loving with them. She kept me up to date both am and pm via text and pics. She has stayed in my home both times and was responsible, neat and tidy. My babies were relaxed when I returned home both times which tells me that she met all their needs!! It is such a reassurance to have found someone that I can trust to watch them. In the pics she sent me my babies were all cuddled up with her, just as if I were home with them myself. I just couldn't think of a better sitter!”


Evan Hope B.
About: Over the years, I have built a reputation as a reliable and caring dog walker and pet sitter, looking after both small and big dogs for multiple friends and neighbors. My experience spans various breeds and temperaments, ensuring that each pet receives personalized attention and care. Whether it's a quick walk around the block or extended pet sitting services, I provide peace of mind to pet owners, knowing their furry friends are in good hands! As a nursing student and extern, I maintain a flexible schedule that allows me to accommodate any pet parent's needs with proper notice. Pet care is an integral part of my daily routine, and I take pride in being able to balance my responsibilities while providing exceptional care for your furry friends. My reliability and dedication ensure that your pets receive the attention and love they need, no matter how busy life gets! When taking care of a client's pet in their home, I make sure to follow their rules and wishes to the letter. I understand that every pet has its own routine and preferences, and I am committed to maintaining that consistency. From feeding schedules and walking routines to playtime and specific care instructions, I ensure your pet feels comfortable and secure while you're away. Your peace of mind is my top priority, knowing your furry friend is in familiar surroundings and well cared for.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. 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 Winslow is $40
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 Winslow average 5 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 Winslow on Rover as of Aug 2025 was about $40 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 Aug 2025, there are 59 house sitters in Winslow. 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, 83% of Winslow house sitters respond in under an hour.
House sitters with repeat customers have an average of 5 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 Winslow.
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. Winslow 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.
