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!”
“Laura is great and my puppy loves her! Shes great with a pup who’s still learning her manners. Knowing she was coming to hang out with Eloise put my mind at ease when I started going back to the office after adopting her. Definitely recommend!”
About: Hi! I’ve grown up with animals my whole life. Having experience from yorkiepoos, cats, Dobermans, pitties and horses! I am comfortable with any size and age of pet, and understand that every animal needs something different. I work full time in health care so I am looking to walk or pet sit and walk in my off time. I’m can assure you I will provide the highest quality of care for your animals. I can do most nights during the weeks (maybe even some mornings) , and my weekends are free! I will also occasionally have some off days! I have a fenced in yard and and very walkable neighborhood. I am also open to staying in homes for pet care and house sitting.
About: I have two pet snakes and have grown up around cats and dogs my whole life! I’ve given oral and injectable meds to snakes, cats, and dogs so I’m perfect for even high needs pets. I’m currently working part time, so I can work around a usual 9-5 schedule. If you have longer sitting needs, reach out and I can make something work for you! I will depend on the systems and items in your home according to your pet goals and needs! I come prepared with curiosity and kindness with every pet and I’m not afraid to ask questions.
“Don was fantastic with my 9-month old puppy. He is reliable and prompt for the drop in visits. I could tell during the meet & great that my pup already liked him. He fed, walked and even did some training (loose leash walking, stay and come) which was very appreciated. Highly recommend!”
“We’ve used Liz for our 7 month old puppy for about a month now and she’s been absolutely amazing! Liz has been incredibly flexible with our schedule, even doing a last-minute meet and greet before getting started and accommodating last-minute requests when our schedule changes. She takes such great care of our puppy and always sends thoughtful updates about how his day went, which we really appreciate. Our puppy Bogey absolutely adores her and looks forward to seeing her every visit! It gives us so much peace of mind knowing he’s in such good hands. We highly recommend her!! Thanks for all that you do Liz!!”
About: I’ve always loved animals and have been caring for pets for years. I have grown up with dogs my entire life! I’m dependable, attentive, and treat every pet like they’re my own. I’m comfortable with dogs and cats of all ages, and personalities, and I understand that every pet has their own routine and needs. Whether it’s walks, playtime, feeding, cuddles, or simply keeping them company, I’ll make sure your pet feels safe, happy, and loved while you’re away. I’m responsible, communicative, and happy to follow any special instructions you have. Your pet’s comfort and well-being are always my top priority! I work remotely most of the week, with the exception of Tuesdays, which gives me a lot of flexibility to pop in and care for your dog or cat during the day. I love being able to provide pets with attention and companionship throughout the day rather than having them spend long hours alone. When caring for your pets in your home, I focus on keeping them comfortable, happy, and on their normal routine. I’ll follow all instructions you provide for feeding, walks, potty breaks, medications, playtime, and any other special needs. I’ll give your pets plenty of attention and companionship while also respecting their space and individual personalities. Since I work remotely most of the week, I have the flexibility to stop by during the day for walks, check-ins, feeding, and playtime. I’ll also make sure fresh water is available, litter boxes are clean, and your home is left neat and secure after each visit.
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!
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.
About: *Fee of $30 will be applied for last minute bookings.* "I had dogs like German Shepherds, Siberian Husky's, Doberman, Saint Bernard, and Dachshunds growing up as a kid. Always was around dogs/cats during my childhood. Friends and family have relied on me to walk, feed and bathe their furbabies. I love animals and love their unconditional love! They are not just pets, They are children and grow with us <3 *Please message for a promo code for $20 off your first booking! I’m currently working at home. Basically around my computer so I’ll have plenty of time to play with your pups and/or cuddle up to your cats! Definitely able to walk your dogs freely for some fresh air and potty breaks. I’m available for boarding on weekends, and weekdays after 11am.. But if you would need to do earlier, sure we can arrange that if needed. I live in apartment building with special a amenity for pets, a Pet Park! I have a friendly Shiba Inu girl puppy, who loves interaction. Sure she would be have blast as well with your doggy to keep your fur baby company. I can easily crate your dog if needed… Btw they are allowed on couch/bed. No issues there. I’m working full-time from home, so I’ll have plenty of time to play with your pups! I’m available for boarding on weekends, and weekdays after 2pm… I have friendly Shiba girl puppy who's friendly, help your fur baby company. I can easily crate your dog or cat if needed… Seems that I'm a natural with dogs and they gravitate towards me, create a instant bond! Family is safe with me!
About: I have been around pets all my life currently had 3 pets at home 2 cats and a dog border collie I take care off my friends and family pets wen they are away for vacation Im currently working Monday through Friday mornings I will be available to take care of your pets after 3 pm Saturday and Sunday im available all day I don't have a yard but I live two minutes away from Morrison Park which is a large and calm area to walk your dog and it's perfect.
“Alex was great to work with! He went above and beyond- stopping by for extra playtime, changing the litter, and troubleshooting our water fountain while we were gone. Took great care of our cats while we were away for our honeymoon”
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 have had animals all of my life- cats, dogs, guinea pigs, fish, newts, frogs, hamsters gerbils, parakeets and even an ant farm at one point! I have helped pet sit for other people and my daughter also does pet sitting. I have been a nurse for 37 years and I also volunteer at Nevin's Farm weekly. I know how important it is to have a reliable person to check on your animals while you are away or just at work. I would like to expand what I do and be that person for you. I work at the hospital three times a week and on my off days I am available to come check your pet, give them potty breaks, feed them, whatever they need to make them comfortable while you are not there. Sometimes my days might vary but hopefully a routine could be established that suits us both. I am happy to go by any instructions you leave for your pet - where they are allowed to go or be, what you want me to put out for them for food or water, etc... Just let me know because I want to keep their routine and environment the same as if you were there in that moment. I would like to think that if my animals could talk they would give me high marks for all I do for them to keep them clean/cared for/walked. I think they are happy with me!!! But I guess I do something right as my friends and family always call me for advice or when they want to adopt and say "Where should I go? What do I need? Is this a good choice? Will you go with me?" So I take these asks as good compliments.
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?
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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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