Dog Sitting Winchester
Book a Winchester dog sitter to watch your dog in your sitter’s home or yours.
Over 273 pet parents in Winchester have booked dog sitting
Winchester, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Sherry was amazing! We decided to go on a last minute trip and she met with us the night before we left. She was so nice and a joy to be around so we knew Charlie would love her! This was our first time leaving him but we were reassured by her personality. She did everything we wanted and more. We can't thank her enough and we highly recommend her! We will definitely use her services in the future!”
About: What sets me apart from other sitters is my lifelong experience with animals, having grown up with dogs and cats in the country. I provide compassionate care for senior pets. My joyful, hardworking, and caring nature for animals ensures each pet receives the personalized attention and love they deserve. I am a flexible and reliable pet sitter available anytime with advance notice. Ready to provide loving, attentive care for your pets whenever you need! I provide attentive care in my clients' homes. For outdoor time, I use a leash to ensure safety and proper exercise. Your pets will receive personalized attention, love, and regular activity.
About: I have all kinds of pet care experience. I love any and all pets including the reptiles and fish! I myself have a long haired dachshund and a long haired cat I currently work part time so I have plenty of free time on my hands. I do not drive due to personal reasons but I do have reliable transportation. I like to meet my clients a couple days prior to watching their pet. I would like to have a conversation making sure I understand everything correctly.
About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)
“Cynthia did such a great job with our new pup who is still learning. She was very patient with her and kind. I loved getting updates and photos of their visit everyday! Will definitely use Cynthia again in the future!”
“We had an amazing experience with Darian! She did a phenomenal job caring for our dogs while we were out of town. We felt reassured from the moment we left knowing they were in good hands. She went above and beyond—keeping us updated with photos and messages, ensuring they stuck to their routines, and showing them so much love and attention. It was clear she genuinely cared for our pups, and we returned to find them happy and well cared for. We couldn't have asked for better care, and we will absolutely book her again in the future! Highly recommend! 🐾”
About: Grew up with Dachunds, then had 3 large dogs during marriage now I have the youngest one left with me Baylee May about 6 yrs old. I often dog sat for multiple friends and family. I am very flexable. I do not currently have a full time job and only am busy when my step children need to be taken to school in the mornings, but even that only takes an hr out of my day. I am extremely reliable and trustworthy. I value and respect peoples homes, items and ofcourse their pets. I would always treat every pet the way I expect people to treat mine. I can provide refrences if needed.
About: I’ve taken care of my dads friends dogs aswell as my own cat. I’ve fed, walked, etc.. I’d love to work with your pet! I’ve had my cat for 12 years and she’s well taken care of. This is currently my main priority as I’m going to college soon! I can do pretty much any days and any times!! Monday-Friday. 7Am- 9PM (just an example) I currently do not offer this ! But if i ever did I’d make sure your fur baby is as comfortable as my own. Thank you for trusting me!
“David did an outstanding job taking care of my cat, Jaxson, while I was out of town. He was very communicative throughout the entire stay and regularly sent photos and videos, which gave me a lot of peace of mind while traveling. Jaxson can be territorial and isn't always the friendliest cat with new people, so I was pleasantly surprised to see him playing and interacting with David. That alone tole me a lot about his patience and ability to connect with animals (the cat whisperer). I can tell he loves all animals! David also went above and beyond with the little things. He kept the litter box clean, rinsed out the food cans, left everything neat and tidy, and figured out a few household routines that I forgot to explain. When I returned home, everything looked great and Jaxson was happy and well cared for. I trusted David with access to my home while I was away, and he proved himself to be reliable, thoughtful, and professional. I would gladly hire him again and highly recommend him to anyone looking for a dependable pet sitter.”
“Nikita showed his skills as a dog handler from literally the moment he walked in, greeting the shy dog so skillfully that she happily went right up to him to say hi. He was great with rambunctious Duncan and my very energetic young puppy Holly, managing to keep them playing safely together until they were tired enough to give me a few hours of peace before they recharge their energy. I'll definitely book Nikita again!”
“This was the second time I’ve had Katie check on my three cats while I was away and just like last time, she was absolutely amazing! She even threw a birthday party for my two girls, who share a birthday on July 4th. I am so beyond grateful to have found a pet sitter that has such a genuine heart for animals and gives the absolute best care. I will absolutely be booking Katie every single time I need someone to check on my babies! You can trust that she will give your pet(s) the best care and love while you are away. Thank you again, Katie! My cats will certainly be happy to see you again (especially Meejum lol)”
About: I am a dependable and compassionate pet caregiver with hands-on experience caring for dogs and other household pets. I understand that every animal has its own personality and needs, so I take the time to build trust while providing attentive, personalized care. My experience includes feeding, walking, administering medications when needed, cleaning up after pets, providing companionship, and maintaining consistent routines to help them feel comfortable and secure. I am proud of my commitment to treating every pet like family. I pay close attention to behavior, energy levels, and overall well-being so I can quickly notice any changes that may need attention. I communicate regularly with pet owners, provide updates and photos, and always strive to give them peace of mind while they’re away. I am patient, reliable, and genuinely enjoy spending time with animals. Whether caring for energetic puppies, senior pets, or shy animals that need extra patience, I provide loving, responsible care that keeps pets happy, healthy, and safe. I work from home with generous breaks. While my schedule is 9-5, I wake early to go on walks in my neighborhood, and my work day includes 1.5 hours of breaks. After work is much like “before work”. A pet would work perfectly in this schedule I have a 3 story townhome and garage! I recently installed a fence! I will keep the pet entertained with fetch, and other stimulating games and puzzles
About: Hi, I’m Kiana! 🐶💛 I’m a dedicated pet lover who genuinely enjoys caring for dogs and making them feel safe, comfortable, and loved while their owners are away. I have experience caring for dogs of different sizes, breeds, and energy levels, and I’m happy to follow their individual routines, dietary needs, and any special quirks that make them unique. I’m a personal trainer and Pilates instructor with a flexible schedule, which allows me to check in on dogs throughout the day during breaks and spend quality time with them between my sessions. Whether it’s walks, playtime, potty breaks, feeding, or simply keeping them company, I’ll make sure your pup gets plenty of attention and care. I know how important it is to feel comfortable leaving your furry family member with someone you trust. I’ll follow your instructions closely and send regular updates and photos so you can have peace of mind while you’re away. 🐾 My goal is to make your dog feel happy, safe, and right at home while you’re gone. I’d love to connect and learn more about your pup! 💛 I’m usually up early for the gym, so I’m comfortable with early-morning walks and care. I’m also available on weekends, when I enjoy taking long nature walks and would be happy to bring your dog along if they enjoy outdoor adventures. I live in a very spacious apartment with a balcony. I do not have any kids, so my environment is dog friendly! I am typically always home, so extra care and safety will be provided for your furry baby. I am now accepting only one dog at a time so that I may provide the best experience for your Furry Babby 🐾🐾🐾
About: Hi! I’ve had a dog since I was a toddler and I’ve always been fascinated by dogs/pets, and caring for them. I love spending time with them, playing, walking and having fun! I’ve always considered them an extended part of my family, which makes me understand how importante they are in our lives and that they have needs just like everyone does! Part of those needs are caring, helping them keep themselves active, proper feeding and to stay healthy, no matter their age, breed or condition. Time apart from them can be tough, but by showing love and care, I help them to relax, have a good time, and to wait for you to be back with them! 🤗 I currently work part time, which gives me a lot of flexibility, and time to spend with my furry friends 🐶 I also have a car, that lets me move quicker and helps me attend my pet-guests 🥰 I have a large fence backyard and a sweet brown lab named Cocoa, who’s always happy to receive guests! In case our furry friend is not interested in having company, she likes giving them space. There’s plenty of room to keep them separate 🧘🏽
The median cost per visit for dog sitting in Winchester is $20
Dog parents share their Rover experiences - Winchester
From our very first meeting, I could tell Alex was completely comfortable with our big, overly excited boy. Franky loves his walks and having someone to spend time with, and I really feel like Alex is going to be a wonderful friend and walking buddy for him. 🐾❤️
I am very happy with Christa! She did an amazing job with my pups. Bo and Sheena are very happy too. This was my first time using this service and I’m so happy that I found Christa. It’s not easy for me to leave my pups with anyone. Thank you Christa for being so kind and friendly to my pups. I will definitely be using these services again and request for Christa.
Karen was great! We had a trip planned and Whiskey had been sick since November. Thought he would get better but still had a lingeri g cough. We had another sitter lined up who had their own dog and we didn't want that dog to get sick too. I found Karen last minute to come to our home and take care of Whiskey with dropins. She did such a great job and kept us informed on his coughing. Thank you so much!
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 sitting
1. Search
Browse profiles of sitters near you who offer dog sitting.
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 sitting - Winchester
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winchester average 5 repeat dog sitting clients
FAQs for Dog Sitting - Winchester
Frequently asked questions about Rover
The average cost of Dog Sitting in Winchester on Rover is $22 per visit as of October 2026. Most bookings cost between $11 and $26 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 829 sitters on Rover offering Dog Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winchester choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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 .
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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winchester with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winchester. On Rover:
- 92% of sitters can help with special care needs
- 94% 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.
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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