Dog Sitting Winchester
Book a Winchester dog sitter to watch your dog in your sitter’s home or yours.
Over 37 pet parents in Winchester have booked dog sitting
Winchester, Find top rated dog sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“I am so thrilled with my experience with Emily. This is only our second time using rover and we have a very energetic and unique 2year old dog so it can be nerve wracking, but she was understanding and amazing with him. She made note that he didn’t go to the bathroom on their walk so made sure to take him out again before she left which shows how much she cares. She also used some commands with him which is great for him to practice. She followed my directions on where and how to walk him and they played with his favorite toys. We got plenty of adorable photos of their time together. Will definitely be reaching out again for future drop ins. Thank you Emily!”
“Kat was great with Bella! Bella enjoyed the time that Kat spent with her. I enjoyed getting the pictures of Bella every time Kat came over while I was gone and seeing how happy Bella was! Thank you Kat for taking care of Bella and my mums!!!”
About: I am an experienced dog owner with a lovely chocolate lab at home who always likes having friends over! I will care for your dog like I care for mine. I have a large fenced backyard for our furry friends, and I usually go for a daily hike to the Fells Reservation just a few minutes away. Working from home with a flexible schedule allows me to take care of all your pets needs. Ie I go for hikes/walks during the day depending on your dog's needs. Large fenced backyard in a safe residential neighborhood, close to the Fells. My chocolate labrador retriever is extremely friendly and gets along with other dogs.
“Sophia is great! She was available when I needed last minute Labor Day weekend drop ins for my cat. I liked her immediately, and she took very good care of my Sam. He definitely warmed up to her after just 1 visit. Will absolutely hire Sophia again!”
About: I grew up with our own dogs as well as 25 foster dogs over the years. Five years ago, I adopted Eddie, my 14 year old chihuahua mix. In May, I adopted Dolly, my 10 year old Boston terrier mix. I’ve taken care of puppies, seniors, 110 lbs dogs, 10 lbs dogs, and everything in between! I’d love to be able to help you and your family. I’m a teacher currently on summer break, so my schedule is completely free for the summer. Once fall hits, I’ll still be available during the afternoons and on weekends. I truly think that owners know their dogs best, so I will take the lead from you in regards of what your dog expectations are. Each pet has different needs, so I’d like my care to reflect their needs and approach each situation holistically
About: I have grown up with animals all my life! I first started walking my neighbors German Shepard when I was 12 years old and I grew up with three cats in the our household. I had my own dog Guiness who was a silly goofy boxer until last year. I’m comfortable around any size dog as well as cats I have a unique work schedule where I have pretty early shifts so please take a look before scheduling! I work Sunday 9am-3pm, Monday 7am-4:30pm, Tuesday 6am-3pm, Wednesday 7:30-3:30p as well as later a shift on Thursdays 12pm-8pm so I have availability most people won’t have with an 8am-5pm job. With working Sunday-Thursdays, I’m available all day On Fridays! When I had my dog this schedule was really nice so he would only be left alone at home for around 4 hours at a time. I know how important it is to make sure your pet gets their energy out and bathroom breaks when you’re not there. I make sure any environment I’m in is clean and pet friendly whether that means crating your dog if they need to be after visiting or making sure I’m aware of my surroundings in walks. My dog was reactive towards other dogs so I have experience with reactivity and will be aware of other dogs while on walks. During visits I would love to play with your pet with their toys, puzzles, or lick mats whatever they need I’m there! I do have experience giving dogs medication as well if that’s something you need! I don’t have experience giving cats medication.
“Maria is so kind and goes above and beyond to make pet sitting great. She offered to meet and greet our cat before we left and really went the extra mile to make us feel secure. Would highly recommend her to anyone in need of a pet sitter.”
About: I have grown up with dogs of all different breeds and sizes throughout my life and they have become a constant part of my life. My parents, aunts, and uncles have always had dogs growing up as well, and they truly become members of the family. I have watched all my families dogs and also worked at petsmart in the pet hotel for three years. I expect the high level of care that I have given my pets when I have looked for care for my own animals. I have watched dogs through rover now for around three years and have plenty of great reviews . We love having dogs of all sizes and breeds and our dog blue loves all dogs that come over to stay
About: I’ve had dogs and cats my entire life, and caring for animals has always been something I truly love. While I’m not able to have pets of my own right now, I’d love the opportunity to give that same love and attention to your pets! I work from home on a hybrid schedule, which gives me flexibility to provide walks, drop-ins, and plenty of companionship when I’m available. I’m also happy to care for pets on weekends when I’m around. My goal is to make sure your pets feel safe, comfortable, and loved while you’re away — and to give you peace of mind knowing they’re in good hands. 🐾 I work from home on a hybrid schedule, which gives me a lot of flexibility to care for your pets throughout the day. On my work-from-home days, I’m able to provide plenty of attention, companionship, and breaks for walks or potty time. I’m also available on weekends when I’m around and happy to work with your pet’s routine and needs. Since I’m currently unable to have pets of my own, I’m excited to use my flexible schedule to give your pets the love, attention, and care they deserve! Unfortunately, I’m not able to have pets in my own home due to not having a yard and living with people who have severe pet allergies. I don’t have any pet allergies myself, though, and I’m more than happy to travel to your home to provide care wherever your pets are most comfortable!
“Alexander was a very kind and responsible care provider to our two darlings and his extra care and communication was very helpful as we changed a couple of routines for our cats just when he came to care for them. Our shy kitty even interacted with him! I highly recommend Alex if you need a caring and attentive cat-sitter.”
About: Hey there! I’m a doctoral student and recently moved to the Boston area. My past three years of experience on Rover has been in Ohio, and I’ve been able to meet and take care of so many furry friends :) Would love to start building my clientele in Mass! Also a really big fan of getting free dog therapy & cuddles as i’m surviving grad school 😅 I adopted a rescue dog, Scooby, and he is my whole heart. I’d love to take care of your fur baby and they’ll definitely have some fun with Scooby if your fur baby does great with other dogs. All playtime will be supervised, and Scooby is also crate trained. Scooby is super playful and I know he would love to make some friends in Mass! While I don’t have my head crammed in a book studying, I’ll be very attentive to your fur baby’s needs, and they’ll have some fun too during their stay 😁 I am frequently home during the weekdays and weekends. When I’m not in class, I am typically studying and have frequent access to my home, and am able to pop in between classes! Morning, noon, and evening walks are easily accommodated into my schedule, and I am generally free on weekends I care about your fur baby getting plenty of attention and playtime. Having an Australian cattle dog, I know a thing or two about dogs needing to release some playful energy and why quality time with them is so important to keep them happy and stimulated. I care that your pet is happy and safe during their stay!
“Annika was an amazing cat sitter! She made sure Zelda had food, water, and a clean litter box, then spent some quality playtime with her and sent some sweet photos. Would highly recommend her to take care of your pets!”
“We had a great experience with Annette! She took the time to come beforehand and learn our guinea pigs’ routine, which we really appreciated. She was reliable, attentive, and took great care of them while we were away. It gave us peace of mind knowing they were in good hands. Highly recommend!”
“Zijia took amazing care of my cat while I was away. My cat is usually shy around new people, but he warmed up quickly thanks to his gentle and patient approach. I came home to a happy, relaxed cat and a clean space. I would absolutely recommend Zijia to anyone looking for a kind and reliable pet sitter.”
About: I’ve been around animals my whole life and have hands on experience with both cats and dogs. I’ve rescued and cared for kittens, helped train dogs, and have plenty of experience with daily walks, feeding, playtime, and keeping pets on their usual routine. I’m comfortable with all kinds of personalities and enjoy getting to know each pet. My schedule is pretty flexible, so I’m available for walks, drop ins, and pet sitting throughout the week. I’m happy to work around your pet’s routine and can usually accommodate different times with advance notice. know how hard it can be to leave your pet with someone else, so I always want you to feel comfortable and reassured. I’ll treat your pet like my own, follow their routine and your instructions, and give them plenty of love and attention. I’m also happy to send photos and updates while you’re away if you want!
About: Reliable and attentive dog sitter who treats every pet like family. Strong communication, patience, and consistency help dogs feel comfortable, safe, active, and cared for while their owners are away. Pet care fits naturally into my daily routine because I am organized and consistent. I plan my day around scheduled walks, feeding times, and check-ins to ensure each dog receives reliable, attentive care. I typically work from home so it makes things more manageable. I am available to care for pets on a flexible, as-needed basis and can accommodate both occasional and recurring bookings in clients’ homes depending on their needs.
“I just returned from a last-minute trip. I contacted Haowen two days before, and he was super accommodating. We met two days before my flight. My dog immediately warmed up to him, and I knew he would be great with her. During the trip, he sent me tons of pictures of them walking and playing. He's a great person, and I would definitely recommend him! I'm going to be a repeat customer, too! Thanks so much, Haowen!”
The median cost per visit for dog sitting in Winchester is $25
Dog parents share their Rover experiences - Winchester
Carmen has been wonderful with our two dogs! The big one just loves cuddles with her and the small one loves playing fetch with her. We have engaged Carmen for regular drop ins and also special dates when we had to be away. She has always been super reliable and a very clear communicator.
This was our first time working with Nina and we look forward to working with her again. She is friendly, kind and attentive and we felt comfortable that she was a good match for us and with our dog and cat. She responsibly followed our guidance on food and meds which was very important as our dog had suffered a recent injury. We requested and received regular updates on how our little guy's were doing, giving us great peace of mind while we were away. She also sent very cute pictures!
Monica has been so terrific watching Willow while we are at work. Willow was recovering from an Injury and Monica adapted wonderfully to assist her as needed. and Monica’s positive attitude, flexibility, and frequent updates make her one of our favorite pet-sitters ever! Strongly recommend!
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 6 repeat dog sitting clients
FAQs for Dog Sitting - Winchester
Frequently asked questions about Rover
The average cost of Dog Sitting in Winchester is $28 per visit as of October 2026. Most bookings cost between $15 and $34 per visit. On Rover, 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 10,102 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:
- 85% of sitters can help with special care needs
- 90% can help with giving oral medications or injections
- 94% 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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