Dog Boarding Winston
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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.
“Jocelin and Christian did an exceptional job caring for our pups. Jocelin shared pictures daily and made extra effort to give them the exercise our high energy young ones need. I highly recommend Jocelin for boarding your dogs.”
“Julie did a wonderful job caring for my Marli! She provided updates and photos while I was on my trip. I could tell that Marli really enjoyed playing with the other dogs in Julie's large yard as she came home very tired. I plan to use Julie again in the very near future! I highly recommend her services!”
“This experience was amazing! My doggies came home sooo happy and got so much outside play time. She was so sweet and responsive. I hope to have the opportunity to use her for our next trip.”
“I've lost track of the number of times our pup has stayed with Heather & her husband! She is reliable, consistent and above all, a truly kind and caring person. Our vacations are worry-free because we know Lucky is in good hands with Heather!”
“Fantastic experience, Jennifer’s frequent updates and pictures allowed us to be able to relax and enjoy our vacation. Her dog Charlotte and our puppy played well together. Our puppy keeps asking to go back. Totally will use Jennifer again, and highly recommend her.”
“The BEST! We were hoping to find someone who cared for our little guy like we do and we found her. Linda and her family are amazing and deserve 6 stars. We will be using Linda's boarding services many, many more times!”
“I am sorry Laurie that I am so late, with this review. Laurie is such a sweet woman. She took such good care of my Lyric. I have only used one pet sitter to keep Lyric since she was 3 months old and I was nervous about taking her to anyone else. Well Laurie treated Lyric like one of her own and Lyric was enjoying herself the entire time. Laurie kept me posted the entire visit with pics, texts and videos. Thank you Laurie for being such a kind soul.”
“Our girls were loved and very well cared for. 🩷 As parents, we could not ask for more. Svetlana is compassionate for your fur babies and you the parents. 🥰 We received videos that helped us to enjoy our time away, because we didn't have to wonder how they were doing. We are grateful for Svetlana. 🐾”
“Rebecca was great with Dani. She sent me pictures of Dani daily. Rebecca has a large fenced in yard for the dogs to play and run around in. Dani loved being able to play with the other dogs. I will book Rebecca the next time I need doggie sitter.”
“The only person we are 100% comfortable leaving our fur baby with when out of town. Our girl is shy and struggles with separation anxiety except when she is at Tara’s. She walks right in to her home just like she does at ours! Excellent communication and flexibility in scheduling when challenges arise.”
“Lorena took such great care of my pup Appa! Her large fenced in backyard allows ample play time and exercise for the pups at her home. I was so happy to see the many pictures she sent me while my husband and I were away. I know Appa had a wonderful time and we are all looking forward to our next visit! Thank you, Lorena!”
“I felt so at ease for my sweet pup under Heather’s care. She sent me pictures and updates everyday on my two week trip, and Lark settled in rather well and LOVED her dogs and cats and felt a part of the pack! We will definitely be using her again in the future 😊”
“Scott and Sarah were fantastic! They provided regular updates, took our dogs on long walks and hikes and even made suggestions on how to make walks easier for our excitable young lab who likes to pull. They will be our first choice any time we need dogsitters!”
“Jason and his wife were absolutely amazing with my basset, Chewie! They stepped in on a last minute request and gave him all the love and care I could have hoped for. It was clear from the start that they truly love dogs, and Chewie felt right at home with them. I got updates that gave me complete peace of mind, and I could tell he was happy and well looked after the entire time. I couldn’t have asked for a better experience! Jason and his wife went above and beyond. I would highly recommend them to anyone looking for trustworthy, caring, and reliable pet sitters.”
“Very pleased with the service rendered. I never had to question whether or not my dog was being taken care of. Jessie is very personable, and professional. I will definately be using her services again, if she'll have Gatsby back. Highly recommend, you won't be disappointed!!!”
“Beth is always great with Marvel, she welcomes him into her home like her own. She sends pictures and videos so you know thier okay, even gave him a bath after the rain. she is also very understanding, my plane was delayed and I appreciate that so much because I hate to inconvenience others.”
The median cost per night for dog boarding in Winston is $45
Dog parents share their Rover experiences - Winston
Jocelin is amazing. We used her to board my dog a month ago. As we drove into the neighborhood for my dog's second boarding, my dog started whimpering with excitement, then upon arrival jumped into Jocelin's arms wagging her tail and then ran to the front door! Clearly a testament to the care and attention she had received the last time! Also Jocelin is super responsive and I can't recommend her more to care for your loved pet!
Both our dogs stayed with Kristi for 10 days and she and her husband were wonderful with them. Kristi sent us regular updates with pictures and was great to communicate with. She also did not hesitate to dog sit our dogs even if one had epilepsy. I would highly recommend Kristi and will probably use her service again when the time comes.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Winston
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winston average 14 repeat dog boarding clients
FAQs for Dog Boarding - Winston
Frequently asked questions about Rover
As of November 2026, there are 372 sitters on Rover offering Dog Boarding across Winston. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
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.
97% of sitters in Winston can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this 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, we recommend 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.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Winston. On Rover:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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 Rover Guarantee, 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 Rover's Trust & Safety page.
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 VA 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
Connect anywhere with the Rover app
