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

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Top rated Winslow house sitters

“Christianna was so great with my babies. We have a usual dog sitter but he was unavailable due to a family issue and I was so nervous to try someone new but knowing she has animals of her own and has been doing this for so long, really helped ease my anxiety. She came to do a meet and greet and right away they loved her. She sent pictures and updates the whole time we were gone and they looked so relaxed with her!”


“Brittany was fabulous and even my Lab who is afraid of everyone accepted Brittany pretty quickly. She was great with pictures and updates!! Highly recommend!”


“Andrea is absolutely amazing! We have a fairly big farm with lots of different animals. She took great care of everyone and made sure they had everything they needed and more. We’ve already booked her for our next two trips away from the farm. Thank you, Andrea!”


About: == FULL TIME DOGGIE DAYCARE AND BOARDING! == Thank you for stopping by! Please read on to learn more about how we got started in the pet care business. == ABOUT US == We are a military family full of dog lovers (who isn't) and have been since we were children. This journey started after volunteering for a few months at a local humane society and wanting to spend more of our time with dogs. Since starting our Rover journey, we have been trusted with the privilege of caring for many of our friends' and family's dogs. With us, you can be sure that your dog will be in the hands of someone who enjoys dogs and their loving nature! == MEET AND GREETS == We personally do not require meet and greets but are more than willing to accomodate your request to have one, as we understand and value a mutually harmonious fit between all parties. Meet and greets will take place in the front yard and be limited to 10-15 minutes. Also, please know that we do not give tours due to liability reasons, however there are pictures on our profile to reference if needed. Our home is spacious, safe, secure and clean! PLEASE NOTE THE FOLLOWING: Daycare rates cover up to 12 hours ( pricing can be adjusted for half days etc) Boarding rates covers 24 hours *If a daycare stay exceeds 12 hours, additional rates will be automatically applied. **If a boarding stay exceeds 24 hours by more than 2 hours, additional rates will be automatically applied. ***A convenience fee of $10 will be applied to any drop off or pick up prior to 7am. Please note that any photos and updates will be sent between the hours of 9am -9pm. If you have any further questions that were not answered here, please feel free to reach out to us. Thanks for reading and we hope to meet you and your best friend! == SCHEDULE == Our family is are full time dog sitters (spouse, mother in-law) and Eric still works his full time job in the military typically 8am-2pm. We are committed to have a dog loving and caring life while balancing our "weekends". We are typically able to accommodate changes in your schedule/needs to adjust pick up and drop off times. Please let us know as soon as possible about any adjustments needed. == DURING YOUR PUPS STAY == Upon a dog's first arrival, we strictly monitor their interactions with any other dog to be aware of any dynamics we need to be concerned about. We do not hesitate to separate dogs into different play areas if anything seems off. Our property is fully fenced on all sides, and we have gates to keep even the best escape artist pups safe. Dogs have full access to our entire downstairs which open up to a well-maintained fenced in yard. == FEEDING == During feeding time, your dog will fed in their crate or a play pen area to prevent food aggression and upset stomachs caused by consuming foreign dog food of other pups. == SLEEPING == Crate-trained dogs will sleep in crates (please specify if your dog is used to a certain size, as we have a wide variety of sizes available. Dogs who are not crate trained will sleep in a pen. Special accommodations can be made for dogs who are not able to do either of those. == WALKS == While it is our goal to make sure each dog get proper exercise and socialization, we do not provide walks during boarding due to liability and risk factors involved with walks (dogs escaping from harness, eating something off the side walk, coming into contact with an unfriendly dog, etc). We do, however give them plenty of outdoor time with the other dogs or solo to socialize and play, which we find is ample exercise for the pups that stay with us. REQUESTED INFORMATION ABOUT YOUR PET Prior to dropping off, please fill out your dog's bio as much as possible. == THINGS WE WOULD LIKE TO KNOW ABOUT YOUR DOG == -Is your pup sick and/or contagious? -Quirks or habits that would be helpful to know (humping, chewing on paws, separation anxiety, excessive barking, etc). -Current or past illnesses, injuries, or traumatic history/triggers. -If they are taking any medication or require any special care instructions. -Is your pup up to date on vaccinations and flea & tick medication. We understand vaccines are not bulletproof and that some illnesses may have an extended incubation period but we highly recommend the vaccines to create the safest experience. *Please know that we are unable to care for sick/contagious dogs. If your pup shows any signs of disease or illness, please let us know beforehand so we can make sure you receive a proper refund. If we discover that your pup is exhibiting obvious symptoms of disease with the first 12 hours with us, your dog will need to be picked up and no refund will be issued. I work 2-3 days a week. Spouse is a stay at home mother. One of us is always at home and available to give your fur baby all of the attention that they need! Trustworthy military member (20 yrs of active-duty service). We can provide care in our home or come to you. I also work as a full-time volunteer for Chesapeake Humane Society helping with dog care team and enrichment.

“If I could give Vanessa more stars I would! The house was in great shape. She straightened and vacuumed the house. Piper and Dilly seemed very well cared for. We trust our girls instincts and they both warmed right up to Vanessa when they met her. I would highly recommend her!”



“Lisa did an amazing job taking care of Apollo. We came home and it was like we never left. She went above and beyond what was expected of her. It’s always nice to not have to worry about your animals while being away. Thank you for being awesome Lisa.”


About: I have taken care of several dogs growing up. I always hit it off with pets from the first time meeting them that people say “Have you met them before?” I love the good energy dogs always give off. I am a healthy active person so I will be able to keep up with energetic dogs but I’m also a laid back person so if you dog just wants to chill k can do that too!! I currently work part time on my own schedule so I have plenty of time to play with your dogs. I am active and work out 5-6 times a week so if you want your dog to get a run in I can do that as well. Anyway they need it. Rather it be playing or walking or cleaning whatever. I will stay in designated areas and will not over step any boundaries set

About: Putting pets and their people at ease with reliable, conscientious care. I have over 10 years of hands-on pet care experience, caring for a variety of animals including cats, dogs, rabbits, birds, and even otters. Since 2014, I’ve consistently provided daily care that includes feeding, walking, grooming, training, administering medications, and maintaining clean living environments. I currently own a Belgian Malinois and two Persian cats, which has given me extensive experience with high-energy and high-maintenance breeds. My background includes not only routine care, but also behavioral training and attention to the unique needs of each species, demonstrating both responsibility and a strong passion for animal welfare. I’m a military spouse, at the moment I’m going to be available any time of the day and night. Text and calls are available all week 24/7. Also I’m I full time mom, I have a 3 year old boy, he is always with me, that’s why I choose this job so I can have the opportunity to work choosing my own schedule. He is a sweet boy. I don’t have a fence at my home, but I always take my dog on a leash outdoors for a potty break and also to have a time for a walk.

About: I may just be starting out, but I love animals, and I love taking care of them. I will make sure your pets are taken care of and their care will be my priority! I am about to get out of the military, and I’m still waiting on updates about my new job, so I will be able to fit this into my schedule, mostly on the weekends. I always let my dog roam free, and I took him on walks every day for his exercise. You just tell me what specific care your pet will need, and I will make sure they get it.

About: Highly expierienced in dog care, cat care, horse care, donkey care, chicken care. Vet tech expierience lots of grooming expierience from puppies and kittens to baby chicks all the way up to geriatric cats and dogs and horses! Im well skilled to care for your pet the way you do when you cant be there!!! I treat all my guest furbabies just as spoiled as my own !! Its truely my passion to help animals be happy and healthy! Growing up working in vet offices, grooming dogs for dog shows, caring for my farm animals. I have lots of time working with so many differnt animals and breeds! I look foward to helping you feel nothing but comfort when leaving your animal in my hands and care! Cant wait to be furever friends! I run and live on a horse farm! So that leave my scheldule pretty flexible aside from being a stay at home mom of my 7 year old daughter and 6 year old son who love animals and have grown up around them their whole life. Crated or loose your preferance! We have 1 acre with a 6 foot saftey fence ans secure metal gate, so rest assured your pet will have plenty of outdoor time while being safe. Im happy to keep cats or dogs or any other animal or do in home drop in visits!

“Trez’Sheer did an excellent job watching my dog. Moose is complicated; he is a senior dog with many special needs. He is a fully blind, partially deaf dog with anxiety. He also takes nighty medication. Trez’Sheer handled all his needs well. She communicated with me daily and quickly whenever I reached out to check in. She stayed in my home, kept my house tidy, and treated my home and dog respectfully. I’d use Trez’Sheer’s pet sitting services in the future if she is willing to put up with Moose again. I was anxious about leaving Moose for eight days, but he was in good hands with Trez’Sheer.”


“Selma did a great job housesitting with our dog Bistro; he really loves her! She sent lots of pictures so I knew that Bistro was doing well while I was gone. We will definitely use Selma again.”


“Tyler did a great job watching Reba, keeping me informed of how she was doing and sending lots of pictures.”


About: I have lived on a farm and taken care of multiple farm animals as well as watched peoples dogs of different sizes. I love to match the energy in the room and look to adapt to make the experience the most comfortable. I am currently flexible as I take gigs one at a time. I will prioritize this job to make sure each animal has the best care. I will listen to instructions and take care of your pet wherever needed. I am aware of fences, doors, and other infrastructure necessary to keep animals safe.

“When I got home, I could tell my dogs were very well taken care of! They loved it! Rebecca was so professional and sent photos of the doggies while I was out of town! I will definitely be using Rebecca again for the amazing service my dogs received!”


About: I have taken care of dogs for about 3 years but I have had my own animals sense I was a kid. I just love being around animals and taking care of them. I want like 6 when I’m in my own house. I am currently pregnant and unemployed I am open when ever you need me and will be there for your pet every second if needed. I will sit and play with them and make sure they are fed and have taken a walk. I like to stay for a bit just so they have a bit of interaction so they don’t miss there people to much.

About: I’ve lived around dogs(all types of breeds and temperaments) for over 35+ years. Family and friends have relied on me to watch their fur babies. I currently work full time, but I am home by 3:30 every day. Weekends are wide open. I pride myself on being flexible and responsible. I’ve cared for a variety of pets : hamsters, rabbits, cats, dogs, and even horses. I take care of your four legged children while you are busy with life. Rest assured they will be loved in your absence.

“Great job and reliable! Was able to watch Dobby with a last minute request for a week. Really appreciate it and it takes a lot of stress away knowing our four legged family member is in good hands.”


About: My name is Haley, I am 25 years old. I am a stay at home mom and fur mom. I am currently going to school online to become a Veterinary Technician, and I hope to become a certified service dog trainer one day soon. I have had dogs my entire life, they are my passion. I have three pups of my own, one being a rescue that I believe rescued me. I would love to use my spare time doing what I love and taking care of some more dogs. I have taken care of every size dog, from a 5 pound Yorkie to a 150 pound Rottweiler. Leave your dogs in the hands of someone you can trust and someone who is going to give them the love and respect the deserve. I am a stay at home mom or two, but both of my kids are in school during the day. I want to use my free time to spend it with animals and helping others with their fur babies I have a large fenced in back yard and I also have multiple crates if they are needed. I make sure to keep water available at all time and give lots of exercise/playtime

About: I have taken care of animals since I was 16 years old. I have experience with anything from home sitting, check in visits, as well as providing animals with medication needs. I love animals and look forward to meeting your sweet fur babies. I currently work at chowan hospital 5 days a week from 8:30 to 5:30 as a occupational therapy assistant. I am free most afternoons and most weekends. Unfortunately I am not able to bring your pets home, but I am more then happy to help make you and your pets life easier.
Loving house sitters in your neighborhood
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Christianna T.
Star Sitter


“Christianna was so great with my babies. We have a usual dog sitter but he was unavailable due to a family issue and I was so nervous to try someone new but knowing she has animals of her own and has been doing this for so long, really helped ease my anxiety. She came to do a meet and greet and right away they loved her. She sent pictures and updates the whole time we were gone and they looked so relaxed with her!”


Brittany B.

“Brittany was fabulous and even my Lab who is afraid of everyone accepted Brittany pretty quickly. She was great with pictures and updates!! Highly recommend!”


Andrea G.
Star Sitter


“Andrea is absolutely amazing! We have a fairly big farm with lots of different animals. She took great care of everyone and made sure they had everything they needed and more. We’ve already booked her for our next two trips away from the farm. Thank you, Andrea!”


Eric C.
Star Sitter

About: == FULL TIME DOGGIE DAYCARE AND BOARDING! == Thank you for stopping by! Please read on to learn more about how we got started in the pet care business. == ABOUT US == We are a military family full of dog lovers (who isn't) and have been since we were children. This journey started after volunteering for a few months at a local humane society and wanting to spend more of our time with dogs. Since starting our Rover journey, we have been trusted with the privilege of caring for many of our friends' and family's dogs. With us, you can be sure that your dog will be in the hands of someone who enjoys dogs and their loving nature! == MEET AND GREETS == We personally do not require meet and greets but are more than willing to accomodate your request to have one, as we understand and value a mutually harmonious fit between all parties. Meet and greets will take place in the front yard and be limited to 10-15 minutes. Also, please know that we do not give tours due to liability reasons, however there are pictures on our profile to reference if needed. Our home is spacious, safe, secure and clean! PLEASE NOTE THE FOLLOWING: Daycare rates cover up to 12 hours ( pricing can be adjusted for half days etc) Boarding rates covers 24 hours *If a daycare stay exceeds 12 hours, additional rates will be automatically applied. **If a boarding stay exceeds 24 hours by more than 2 hours, additional rates will be automatically applied. ***A convenience fee of $10 will be applied to any drop off or pick up prior to 7am. Please note that any photos and updates will be sent between the hours of 9am -9pm. If you have any further questions that were not answered here, please feel free to reach out to us. Thanks for reading and we hope to meet you and your best friend! == SCHEDULE == Our family is are full time dog sitters (spouse, mother in-law) and Eric still works his full time job in the military typically 8am-2pm. We are committed to have a dog loving and caring life while balancing our "weekends". We are typically able to accommodate changes in your schedule/needs to adjust pick up and drop off times. Please let us know as soon as possible about any adjustments needed. == DURING YOUR PUPS STAY == Upon a dog's first arrival, we strictly monitor their interactions with any other dog to be aware of any dynamics we need to be concerned about. We do not hesitate to separate dogs into different play areas if anything seems off. Our property is fully fenced on all sides, and we have gates to keep even the best escape artist pups safe. Dogs have full access to our entire downstairs which open up to a well-maintained fenced in yard. == FEEDING == During feeding time, your dog will fed in their crate or a play pen area to prevent food aggression and upset stomachs caused by consuming foreign dog food of other pups. == SLEEPING == Crate-trained dogs will sleep in crates (please specify if your dog is used to a certain size, as we have a wide variety of sizes available. Dogs who are not crate trained will sleep in a pen. Special accommodations can be made for dogs who are not able to do either of those. == WALKS == While it is our goal to make sure each dog get proper exercise and socialization, we do not provide walks during boarding due to liability and risk factors involved with walks (dogs escaping from harness, eating something off the side walk, coming into contact with an unfriendly dog, etc). We do, however give them plenty of outdoor time with the other dogs or solo to socialize and play, which we find is ample exercise for the pups that stay with us. REQUESTED INFORMATION ABOUT YOUR PET Prior to dropping off, please fill out your dog's bio as much as possible. == THINGS WE WOULD LIKE TO KNOW ABOUT YOUR DOG == -Is your pup sick and/or contagious? -Quirks or habits that would be helpful to know (humping, chewing on paws, separation anxiety, excessive barking, etc). -Current or past illnesses, injuries, or traumatic history/triggers. -If they are taking any medication or require any special care instructions. -Is your pup up to date on vaccinations and flea & tick medication. We understand vaccines are not bulletproof and that some illnesses may have an extended incubation period but we highly recommend the vaccines to create the safest experience. *Please know that we are unable to care for sick/contagious dogs. If your pup shows any signs of disease or illness, please let us know beforehand so we can make sure you receive a proper refund. If we discover that your pup is exhibiting obvious symptoms of disease with the first 12 hours with us, your dog will need to be picked up and no refund will be issued. I work 2-3 days a week. Spouse is a stay at home mother. One of us is always at home and available to give your fur baby all of the attention that they need! Trustworthy military member (20 yrs of active-duty service). We can provide care in our home or come to you. I also work as a full-time volunteer for Chesapeake Humane Society helping with dog care team and enrichment.


Vanessa M.

“If I could give Vanessa more stars I would! The house was in great shape. She straightened and vacuumed the house. Piper and Dilly seemed very well cared for. We trust our girls instincts and they both warmed right up to Vanessa when they met her. I would highly recommend her!”




Lisa B.


“Lisa did an amazing job taking care of Apollo. We came home and it was like we never left. She went above and beyond what was expected of her. It’s always nice to not have to worry about your animals while being away. Thank you for being awesome Lisa.”


Braxton J.
“Braxton is a natural when it comes to pets. The family likes to call him the dog/baby whisperer because of how instant the connection is between the two off of initial meets. He is also a responsible and respectful human being through and through.”


Antonella B.
About: Putting pets and their people at ease with reliable, conscientious care. I have over 10 years of hands-on pet care experience, caring for a variety of animals including cats, dogs, rabbits, birds, and even otters. Since 2014, I’ve consistently provided daily care that includes feeding, walking, grooming, training, administering medications, and maintaining clean living environments. I currently own a Belgian Malinois and two Persian cats, which has given me extensive experience with high-energy and high-maintenance breeds. My background includes not only routine care, but also behavioral training and attention to the unique needs of each species, demonstrating both responsibility and a strong passion for animal welfare. I’m a military spouse, at the moment I’m going to be available any time of the day and night. Text and calls are available all week 24/7. Also I’m I full time mom, I have a 3 year old boy, he is always with me, that’s why I choose this job so I can have the opportunity to work choosing my own schedule. He is a sweet boy. I don’t have a fence at my home, but I always take my dog on a leash outdoors for a potty break and also to have a time for a walk.


Meghan M.
About: I may just be starting out, but I love animals, and I love taking care of them. I will make sure your pets are taken care of and their care will be my priority! I am about to get out of the military, and I’m still waiting on updates about my new job, so I will be able to fit this into my schedule, mostly on the weekends. I always let my dog roam free, and I took him on walks every day for his exercise. You just tell me what specific care your pet will need, and I will make sure they get it.


Rose N.Star Sitter
“Rose is a kind, professional and polite dog sitter. She is prompt and took excellent care of my dog’s needs. I was impressed that she could handle my large energetic Saint Bernard so well right away! Anyone who loves their dog like their child will have peace of mind with their canine in Rose’s hands.”


Trezsheer P.

“Trez’Sheer did an excellent job watching my dog. Moose is complicated; he is a senior dog with many special needs. He is a fully blind, partially deaf dog with anxiety. He also takes nighty medication. Trez’Sheer handled all his needs well. She communicated with me daily and quickly whenever I reached out to check in. She stayed in my home, kept my house tidy, and treated my home and dog respectfully. I’d use Trez’Sheer’s pet sitting services in the future if she is willing to put up with Moose again. I was anxious about leaving Moose for eight days, but he was in good hands with Trez’Sheer.”


Selma M.

“Selma did a great job housesitting with our dog Bistro; he really loves her! She sent lots of pictures so I knew that Bistro was doing well while I was gone. We will definitely use Selma again.”


Tyler M.

“Tyler did a great job watching Reba, keeping me informed of how she was doing and sending lots of pictures.”


Nathan M.
“Nathan is a great individual to take care of pets. He consistently takes care of our three cats and one dog. Nathan has also taken care of other pets on multiple occasions.”


Rebecca R.

“When I got home, I could tell my dogs were very well taken care of! They loved it! Rebecca was so professional and sent photos of the doggies while I was out of town! I will definitely be using Rebecca again for the amazing service my dogs received!”


Holly W.
About: I have taken care of dogs for about 3 years but I have had my own animals sense I was a kid. I just love being around animals and taking care of them. I want like 6 when I’m in my own house. I am currently pregnant and unemployed I am open when ever you need me and will be there for your pet every second if needed. I will sit and play with them and make sure they are fed and have taken a walk. I like to stay for a bit just so they have a bit of interaction so they don’t miss there people to much.


Jamie M.
About: I’ve lived around dogs(all types of breeds and temperaments) for over 35+ years. Family and friends have relied on me to watch their fur babies. I currently work full time, but I am home by 3:30 every day. Weekends are wide open. I pride myself on being flexible and responsible. I’ve cared for a variety of pets : hamsters, rabbits, cats, dogs, and even horses. I take care of your four legged children while you are busy with life. Rest assured they will be loved in your absence.


Sarah W.

“Great job and reliable! Was able to watch Dobby with a last minute request for a week. Really appreciate it and it takes a lot of stress away knowing our four legged family member is in good hands.”


Haley A.
“Haley is a great candidate for this position. Animals have always been her life. The love and gentleness she has for animals is amazing! She is very loving and caring and has a big heart when it comes to dog! Haley’s compassion for all animals would make her an amazing fit for this job! She has taken great care of my dogs in the past and treated them like her own.”


Roslyn B.
“Roslyn has watched my two girls (Sophie and Maggie) numerous times and they absolutely love her! She officially has the title as “Aunt Ros” in our house hold and the girls get so excited to see her! Our dogs are like our children and I could not recommend her enough! She is super trust worthy and very passionate with all of our animals!”
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!
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.
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 $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 Aug 2025, there are 36 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, 88% of Winslow house sitters respond in under an hour.
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 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.
