Dog Boarding Winston

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Winston, Find top rated dog boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Sarah M.
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Sarah M.
from
$35
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
1 year of experience
Asbury, IA, 52002

“We were in town from Atlanta for a family reunion and used Sarah for dog sitting our Rosie. Rosie loved her. She has a quiet and comfortable home. Rosie had everything she needed and was very happy when we picked her up. Sarah’s backyard is great. Rosie highly recommends Sarah!!”

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Betsy K.
Sitter Profile Image: Jacqueline M.
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Jacqueline M.
from
$33
per night
4.8 out of 5 stars
• 22 reviews
11 repeat clients
10 years of experience
Dubuque, IA, 52001

“She took really good care of our pup and even agreed last minute to keep him again for another night (with another booking) because our daughter is sick after our trip.”

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Alyssa W.
Sitter Profile Image: taylor m.
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taylor m.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 174 reviews
61 repeat clients
6 years of experience
Dubuque, IA, 52003

“Taylor was great! She sent lots of pictures and took Millie on a few walks a day which Millie loves. She also gave updates on how she playing with the other dogs that were there which puts our minds at ease.”

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Kaelyn K.
Sitter Profile Image: Cassandra B.
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Cassandra B.
Star Sitter
from
$48
per night
5.0 out of 5 stars
• 102 reviews
28 repeat clients
18 years of experience
Dubuque, IA, 52001

“Lucy had a great time. We were sent pictures while we were gone. Cassie had great communication before and during Lucy's stay. This was overall a great experience for us!”

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Abby N.
Sitter Profile Image: Nicole M.
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Nicole M.
Star Sitter
from
$27
per night
5.0 out of 5 stars
• 55 reviews
18 repeat clients
14 years of experience
Dubuque, IA, 52002

“Did an amazing job was happy to see photos of bean when I was gone. He came home happy and well cared for would definitely use her service again.”

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Joe B.
Sitter Profile Image: Ruth G.
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Ruth G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 28 reviews
4 repeat clients
30 years of experience
Dubuque, IA, 52001

“I can't say enough great things about Ruth! She took excellent care of our 2 dogs while we went on vacation for a week. She provided them with snuggles, walks, and social time and provided us with peace of mind so we could relax. She sent us a few pictures and even some videos! I highly recommend Ruth and we look forward to seeing her again in the future!”

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Kristi K.
Sitter Profile Image: Mya G.
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Mya G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 97 reviews
42 repeat clients
15 years of experience
Dubuque, IA, 52002

“I'm so happy Mya is the sitter I chose. Her back yard is a PUPPY PARADISE... I'm used to apartment living and having to leash walk Luci several times a day. But at Mya's house, Luci can run around in a big secure fenced-in yard with lush grass. It was like a real vacation for her. Mya has cameras on her phone so she can watch the dogs when she's away from the house. She is so chill and welcoming. I brought up my dog's behavioral issues, and she really took the time during the initial meeting to make sure her 4 pups and mine were going to get along OK, and to answer any questions I might have. Her small dogs are very sweet, and Luci made fast friends with them. I got updates with photos and video every day. Overall it was an amazing experience, and I hope we get to make this a more regular thing. Would rate 6 stars if I could.”

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Gabriel M. Falcon ..
Sitter Profile Image: Tamara D.
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Tamara D.
from
$50
per night
5.0 out of 5 stars
• 54 reviews
23 repeat clients
30 years of experience
Dubuque, IA, 52003

“Tamara was great with our pup Roscoe! No issues and we were able to get married without thinking twice about his well-being :) would recommend!”

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Grace N.
Sitter Profile Image: Karen V.
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Karen V.
Star Sitter
from
$25
per night
5.0 out of 5 stars
• 218 reviews
133 repeat clients
45 years of experience
Platteville, WI, 53818

“My experience leaving my doggies with Karen was great. Doggies were happy when I picked them up, Karen was very communicative and send pictures and videos of the dogs. Also she has a great space for them. Would recommend.”

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Lizbeth V.
Sitter Profile Image: Nate I.
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Nate I.
from
$45
per night
5.0 out of 5 stars
• 2 reviews
15 years of experience
Dubuque, IA, 52001

About: I’ve taken care of dogs my entire life, having 6 since I’ve been a child. 2 Portuguese water dogs, 2 pitbulls, and 2 French bull dogs. I have been relied on by friends and family to watch and care for their dogs throughout the years I’m currently a Pre Dental student at Loras. My schedule is open for weekday afternoons and overnight of the week, I can be of service when you need someone to watch your pet overnight or just let them go potty in the middle of the day. In my home we use pee pads, take the dogs on walks, and have a fenced in backyard. We feed them 2-3 times a day, and give them lost of love. I understand how important it is to let the dogs outside while you are away and want to be an option for others like me.

Sitter Profile Image: Angela R.
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Angela R.
from
$30
per night
5.0 out of 5 stars
• 49 reviews
20 repeat clients
4 years of experience
Dubuque, IA, 52001

“Angela was so great with our 2 pups! They had a blast playing with her dog Ellie and giving lots of cuddles on the couch and in bed! She also helped us out with having someone pick up the dogs and being them back so they could be a part of our wedding day! I highly recommend her!”

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Lauren S.
Sitter Profile Image: Cheyenne P.
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Cheyenne P.
from
$25
per night
2 years of experience
Dubuque, IA, 52002

About: I've been taking care of pets for as long as I can remember! Training them, walking, feeding, bathing, and playing are all part of the package! I am almost available all the time. The only days I would unfortunately not be able to see your pets would be on Sunday's and sometime Saturday's for personal days. I am very patient and try to listen to what your pets tell me, but not TOO much! I will always try and make sure your pet has the best time and will be safe 😊

Sitter Profile Image: Ann & Greg M.
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Ann & Greg M.
from
$100
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
40 years of experience
Cuba City, WI, 53807

“Remi loves going out on adventures with Ann and Greg! As a pet parent, I love getting the updates and pictures of him having fun! When life gets busy, I know I can trust Ann and Greg to care for our fur babies!”

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Rose L.
Sitter Profile Image: Matthew & Leah N.
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Matthew & Leah N.
from
$25
per night
12 years of experience
Dubuque, IA, 52002

About: Leaving your dog with someone else can be stressful, but our goal is to make their stay feel like a fun, comfortable vacation rather than time away from home! We are lifelong animal lovers and have cared for pets of all kinds —from dogs and cats to fish, turtles, guinea pigs, and just about anything in between. Over the years, friends, family, and neighbors have continually trusted my wife and I to care for their beloved pets, and we truly enjoy having animals as part of our family. We board only one family’s dog(s) at a time, so your pup gets plenty of personalized attention rather than being one of many dogs competing for care. Our four children, ages 8–13, are also huge animal lovers and are always excited to provide extra attention, affection, and playtime. With six people in our household, your dog will have plenty of companionship and will quickly feel like part of the family. We live on a 4-acre property that gives your dog plenty of space to enjoy new sights, sounds, and smells. For safety, exploring the property is done on leash, and the abundant wildlife in the area provides plenty of interesting things for curious noses to investigate! Your dog will be walked at least once in the morning and once in the evening, with bathroom breaks every 2–4 hours or as needed. During the week, my wife and I have the ability to work from home, allowing us to provide care and companionship throughout the day. We understand that every dog has their own routine and personality, and we’ll do our best to maintain their normal schedule and make them feel comfortable during their stay. We do require dogs to be potty trained and have no history of aggression. We also ask that dogs be trained not to chew on household items or other non-toy objects. We completely understand that puppies are still learning, though, and we’re happy to work with them and provide the patience and supervision they need! Most importantly, we want you to feel confident and comfortable while your dog is in our care. We’re happy to learn about your dog’s personality, routines, favorite activities, and any special quirks that will help us give them the best possible stay. We look forward to meeting you and your pup and welcoming them into our home! When your dog stays with us, they won’t just be a guest—they’ll be part of our family No matter what our day looks like, there is always someone available to provide the attention and consistency of car for your dog(s), which is the number one priority. We also have a furnished basement that can be closed off if needed. Or a quiet capped garage and workshop room depending on the sleeping arrangements your dog is accustomed to. If you could please let me know of any special needs your dog may require or want.

Sitter Profile Image: Alexis S.
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Alexis S.
from
$30
per night
10 years of experience
Dubuque, IA, 52003

About: I am a very attentive and caring dog and cat lover! I have a huge yard and a spare bedroom for all dogs. As for cats, I have two of my own. The spare bedroom can be the cats sanctuary if they do not like other cats as it’s full of cat trees, toys, litter boxes and food and water. I work full time M-F so I would have an open schedule for your pet during the weekend! I have two loving cats who enjoy cats and dogs of all sizes! I have a huge yard for your pups, but it is not fenced in. I also have a spare bedroom for your dog or cat to take comfort in if being alone is their thing!

Sitter Profile Image: Angy E.
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Angy E.
from
$50
per night
5.0 out of 5 stars
• 3 reviews
7 years of experience
Dubuque, IA, 52001

About: I have experience caring for dogs of different sizes and personalities, including feeding, walking, playtime, and providing companionship while owners are away. I understand how important it is for pets to feel safe and comfortable in their routine, and I do my best to keep things familiar and stress-free. I’m reliable, attentive, and always treat every dog with care and patience. I maintain a very flexible routine and am home the majority of the day. I do volunteer a few hours daily, but I’m otherwise available to care for pets, provide attention, and keep them on their normal schedule. Dogs in my care will have a stable environment, regular potty breaks, playtime, and companionship throughout the day. I prioritize safety, trust, and a calm environment for every dog in my care. I make sure pets are always supervised, comfortable, and kept in a clean, secure space where they can relax and feel at home.

Sitter Profile Image: Heather C.
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Heather C.
from
$50
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
40 years of experience
Galena, IL, 61036

About: I've sat for many different breeds and species over the years. I grew up always having some type of animal in the home, especially dogs. I have two dogs and a cat now. I love cooking for them and knowing exactly what is going in their food. I love making home made treats for them as well. I even sew for them at times. I've made boots, coats, beds, Halloween costumes, toys, etc. Right now, my schedule is pretty flexible, which means I have lots of time to dedicate purely to furkids. I am close with a professional dog trainer and am able to ask any question, which is always a big help. My vet has great hours and very accessible as well for any questions or concerns.

Sitter Profile Image: Meg T.
Verified Enhanced Background Check
Meg T.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 27 reviews
4 repeat clients
27 years of experience
Platteville, WI, 53818

“Meg was awesome Benny seemed to feel right at home. She made sure to send us lots of pictures which we love. 100% would recommend Meg for your fur babies thanks again.”

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Tanner O.
Sitter Profile Image: Ann P.
Verified Enhanced Background Check
Ann P.
from
$75
per night
20 years of experience
Dubuque, IA, 52003

About: I have been a pet owner since I was a child. Your pets will be treated with the same love and affection that I would treat my own! My goal is to keep your pet happy and stress-free! I am responsible, compassionate, and focused on creating a positive experience for everyone! If I stay in your home, I will do my very best to keep your pet on schedule while you are away! I will also keep your home clean and the same way you left it when you leave, so that you will come home to a fresh house after being away! I am retired and have flexibility to care for your pup or cat! I can come to your home for potty breaks, walks and play! Want me to hang out with your furry friend. I can do that too! I can also house sit and stay overnight if your pups are used to human connection! I understand wanting your animals to have all the comforts while you are away! I have owned dogs my whole life and understand how they are family to you! I adore all ages and breeds of dogs. Need help with meds and special care. I have patience for that as well! I can come to your home and we can work out a schedule that works for all! You tell me what you want that will put your mind at ease while you are away! I am retired and my schedule is flexible! If you choose to drop your pup at my home… I have two sweet Golden Retrievers. They both get along easily with all! If your pup is not their cup of tea… they will mind their own business! House training? I can help with that too! I have a large fenced in yard that the dogs can burn their energy in! If you want to keep your dog separated from mine, I have the ability to do that too!

Sitter Profile Image: Karen D.
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Karen D.
from
$35
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
30 years of experience
Thomson, IL, 61285

About: I have always loved dogs and cats! I am happy to peek in on your fur babies while you need to be away. Will provide whatever care is necessary. Years of experience! Accommodating, caring and reliable. I will treat your pet just as you would, like family! Whether a walk outside to potty or a quick run around the fenced yard, I will provide you and your pet with outstanding service with attention to detail. Cat care is also available. I will provide service locally. I will always clean up/pick up after your pup. I enjoy snuggling the cats and dogs. I spent 34 years caring for young children so I come well equipped with patience, understanding and compassion. Book a sitting with me today for an excellent, safety conscious visit for your sweet fur baby! I work during the week so this leaves me open to schedule sittings on Friday and weekends.I can come to you or well behaved dogs are welcome in my home on weekends. My schedule can be flexible. Generally Friday- Sunday evening but flexible. I care for the fur babies in the manner they are accustomed to. This keeps everyone happy. I try to do whatever the pup is used to.

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FAQs for Dog Boarding - Winston

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winston home-away-from-home, packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winston.

<b>Tip:</b> You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Winston sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to 25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in IL ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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