Pet Sitting in Winchester

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winchester pet sitters

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

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Sitter Profile Image: Shawnda W.
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Shawnda W.
Star Sitter
from
$27
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
30 years of experience
Roseburg, OR, 97471

Shawna was amazing. She stepped in last min, got me out of crisis mode, worked with my two kitties beautifully, was communicative, responsible, kind, I will rehire her in a heartbeat.

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Kelsey M.
Sitter Profile Image: Dani N.
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Dani N.
from
$27
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Roseburg, OR, 97470

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Casey K.
Sitter Profile Image: Pamela M.
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Pamela M.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
56 reviews
17 repeat clients
60 years of experience
Roseburg, OR, 97470

Pamela was a great sitter for our sweet kitty, Penny! She sent thoughtful updates each day and always made sure Penny got what she needed (snuggles, play, or some tv time!). She also handled Penny’s complex feeding and made sure she had all her meds completely correct. We’ll be sure to have Pamela back to watch Penny.

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Kirk H.
Sitter Profile Image: Megan S.
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Megan S.
from
$30
per visit
5.0 out of 5 stars
37 reviews
10 repeat clients
10 years of experience
Roseburg, OR, 97470

Megan did another fantastic job of taking care of our cats and handling our constantly changing medicine needs. She sent great pictures and updates and clearly cares very deeply for the animals she takes care of! We hope to have her back to watch our cats again!

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Kirk H.
Sitter Profile Image: rashell w.
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rashell w.
from
$28
per visit
5.0 out of 5 stars
19 reviews
5 repeat clients
15 years of experience
Roseburg, OR, 97470

Rashell was really great with my sometimes difficult pup, she also was super helpful being able to make my appointment with short notice... I'd recommend her for your dog!

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Lalo M.
Sitter Profile Image: Helen R.
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Helen R.
from
$20
per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Roseburg, OR, 97471

About: Greeting, My name is Helen. I’ve recently completed my contract in the military. During my time in the service I spent time caring for my colleagues dogs (I do love cats, but I’m allergic) and found myself actually branching out to others when they needed someone to watch their babies. I grew up always having a dog in our family, and know how important they are as family members. Their unconditional love is something I’ve always cherished, and it would be my joy and honor to care for your fur babies whenever. My schedule is flexible, and I am available often. It’s really not a hardship spending time with loving pups. I do have experience with pets that have special needs. I look forward to hearing from you and your fur members.

Sitter Profile Image: Jewels H.
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Jewels H.
from
$15
per visit
5.0 out of 5 stars
1 review
1 repeat client
10 years of experience
Roseburg, OR, 97470

Jewels sent photos and videos so we know our guys got some attention as well as the food and treats they needed. Great sitter!

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Tanya B.
Sitter Profile Image: Dot F.
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Dot F.
from
$25
per visit
10 years of experience
Roseburg, OR, 97470

About: I’ve had dogs in my life since I was 5. and have had my own dog since I was 16 and currently live in a household with 4 dogs. I even have pet sit for friends and family. Proper animal care is like second nature to me, it is my passionate I do have a part time job at a grooming salon and work 4-6 hours tuesday-friday typically. Working in a dog friendly environment I am able to work around potty breaks. Taking care of dogs is basically my whole life, we have 4 of them in our household. I also live with a dog trainer so I have a little bit of knowledge on that as well. Proper pet care is my top priority. I take care of clients animals just like they’re my own. making sure they’re fed and watered and have their enrichment time. If your dog gets along with others I will bring mine for a playmate

Sitter Profile Image: Hallie T.
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Hallie T.
from
$14
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
20 years of experience
Roseburg, OR, 97470

Hallie has become our new regular. Me and my dog fam are grateful for them.

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Erin grey K.
Sitter Profile Image: Nikki C.
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Nikki C.
from
$22
per visit
5.0 out of 5 stars
8 reviews
5 repeat clients
2 years of experience
Roseburg, OR, 97470

Nikki stayed with Lucy for several hours and took her on a nice walk. She also provided me with updates and pictures. Lucy can be high energy but Nikki handled her well

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Lauren R.
Sitter Profile Image: Serenidad C.
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Serenidad C.
from
$13
per visit
4 years of experience
Roseburg, OR, 97471

About: My top priority is always the well-being and happiness of your pets. Growing up with dogs, I've given them unconditional love, affection, and dedicated care, making them my number one focus. I’ve thrown them birthday birthday parties, given them daily walks, organized doggy playdates and visits to the dog park, and taken them on hiking and coast trips to create lasting memories. In addition to providing love and companionship, I’ve trained my dogs in everything from potty training and behavioral improvement to leash manners and more. I’m also passionate about giving back; I actively volunteer at Saving Grace Animal Shelter, where I assist with walking, socialization, and ensuring each animal feels comfortable and loved. I take special care to give them time to go potty, play to burn off energy, and even take them on fun field trips to enrich their lives. Your pets will receive the same level of love, attention, and dedication that I’ve always strived to provide, because they deserve nothing less. I'm currently taking a class at UCC on Mondays, Wednesdays, and Fridays from 12-2 pm. However, I’m available before or after those times, and with boarding, I can accommodate after class on Fridays and weekends. I’m flexible and happy to work around your schedule, so just let me know what works best for you, and we’ll find the perfect plan together! I have a secure, fenced yard, doggy bowls, treats, leashes, and extra beds to keep your furry friend comfortable. If your dog has a tendency to chew, no worries! My home is fully dog-proofed, ensuring nothing gets left out or damaged. I offer a variety of services including dog walking, in-home pet sitting, overnight boarding, doggy daycare, and pet taxi services for vet visits, groomers, and more. Your pet's comfort and safety are my top priorities!

Sitter Profile Image: Laura F.
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Laura F.
Star Sitter
from
$18
per visit
4.9 out of 5 stars
14 reviews
4 repeat clients
50 years of experience
Winston, OR, 97496

Communication was great. Did a Great job.

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Michele G.
Sitter Profile Image: LaShea R.
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LaShea R.
from
$25
per visit
7 years of experience
Roseburg, OR, 97471

About: For the past seven years I have been walking and caring for a dog in my community. I do have experience with elderly dog, and animals with special needs. I currently work a full-time job, but I’m free most weekends, evenings, and holidays to care for your fur babies. Of course if you have any questions regarding dates or times, just let me know. Of course whatever the client is looking for or know is best for their pet is what I will do. Safety is my number one priority with your family member.

Sitter Profile Image: Tom M.
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Tom M.
from
$12
per visit
5.0 out of 5 stars
21 reviews
10 repeat clients
40 years of experience
Roseburg, OR, 97470

Tom has been doing a fantastic job! He deserves five stars. Will definitely use them again and again, it's great to find someone who cares for your dog , And your dog cares for him.

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George H.
Sitter Profile Image: Brittany B.
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Brittany B.
from
$20
per visit
25 years of experience
Roseburg, OR, 97471

About: Since kindergarten, I’ve always had a canine best friend. I can’t imagine life without one! At 15, I fell in love with my first feline companion, and now I can’t imagine life without either. The companionship that animals bring is precious, and that’s why I treat all my clients with the care and love they deserve. My fur family currently includes my dog Beatrice and my two cats, Callie and Fiona. I have over 5 years of experience working as a dog kennel attendant. My passion for animal care continues to grow, and I’m excited to start providing personalized care for other pets in their own homes. I understand that some animals, especially smaller or older dogs and cats, feel more comfortable staying at home rather than in a boarding facility. In 2023, I adopted a senior dog named Becca and had the joy of caring for her for two wonderful years. I was able to arrange for my grandma to watch her while I was away, which allowed Becca to stay on her routine and feel safe and comfortable. Experiences like this have strengthened my understanding of the importance of individualized care. I know every pet is unique and deserves individualized care. I have experience administering medication to both dogs and cats, and I take the time to learn each pet’s personality, preferences, and routines. I genuinely enjoy getting to know each pet and discovering what makes them happy and comfortable. With patience, dedication, and love, I am confident I can provide excellent care and companionship for your furry family members. I also love keeping owners updated with photos and messages so you can see your pet happy and comfortable while you’re away. I currently have full availability! I’m ready to accommodate your pet care needs. I am wanting to provide walks, multiple drop-ins, house sitting, or just longer daytime care depending on your pet’s needs. For drop-in visits and house sitting, my priority is making sure your pet feels safe, comfortable, and cared for in their familiar environment. I will carefully follow your pet’s routine, including feeding schedules, litter box cleaning, potty breaks and waste cleanup, playtime, medication (if needed), and any specific instructions you provide. I understand how important trust is when welcoming someone into your home. I treat every home with respect, keep things clean and secure, and provide updates with photos so you can feel confident and connected while you’re away. My goal is to create a calm, positive experience for your pet while maintaining the safety and comfort of both your home and your furry family member. For dog walking, safety and enjoyment are my top priorities. I have experience walking dogs of all sizes and personalities, from energetic pups to calm seniors. I always use proper leash control and monitor dogs closely to ensure they aren’t experiencing any stress or discomfort. I will make sure to ask if there’s anything specific I should know about walking your dog, like a favorite route or type of walk. I would also love to provide updates and photos during walks so you can feel confident your dog is happy and well cared for while you’re away.

Sitter Profile Image: Katelyn A.
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Katelyn A.
from
$20
per visit
5.0 out of 5 stars
2 reviews
22 years of experience
Roseburg, OR, 97470

About: I have grown up with dogs, raising all of them from puppies (starting at 10 weeks). I also worked for four summers at a dog daycare with dogs of all ages and breeds. At work, I learned how to perform basic grooming procedures, worked with many dietary plans and restrictions, and handled medications. I have also volunteered with shelter dogs and cats with various behaviors and needs. I currently work 4 day weeks, but I have ample free time on my days off I have included in my calendar. Let me know how I can best fit your pet’s needs. I have a dog of my own who is very timid and territorial, so I do not offer services in at my own place. However, I will treat your fur babies with the same love as my own.

Sitter Profile Image: Allie H.
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Allie H.
from
$14
per visit
5.0 out of 5 stars
1 review
20 years of experience
Roseburg, OR, 97471

About: I’ve taken care of dogs and cats since I can remember. I currently have 2 cats and a pup. Friends and family have always relied on me to pet sit, including other animals such as goats, donkeys, and chickens. I work Monday-Thursday, but am always available before and after work (before 7am and after 5pm). I am also available to do drop in visits at my lunch break. I am available all day Friday-Sunday. I have a townhome with a wide field that I take my own puppy out to regularly. I crate train my dog, but do not require if for boarding other dogs. I also have two cats, so I ask for no dogs that are aggressive to kitties. If I am dropping in for visits, I treat your home like my own. I will make sure it is in the same state as it started and will give your pets lots of love!

Sitter Profile Image: Kathy R.
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Kathy R.
from
$20
per visit
5.0 out of 5 stars
1 review
1 repeat client
15 years of experience
ROSEBURG, OR, 97471

About: I've cared for dogs and other pets for 15 years. I have experience in animal care and training for a variety of both domestic and exotic species. I'm an avid runner and I can keep up with the most active dogs! I know my work schedule about a month in advance so I know ahead of time when I will be available to care for your pet. I can drop in and visit your pet to give them some extra attention and care. I love being outdoors so I would love to take your dog on a walk or even a run if they have some extra energy!

Sitter Profile Image: Danita C.
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Danita C.
from
$15
per visit
5.0 out of 5 stars
14 reviews
1 repeat client
12 years of experience
Roseburg, OR, 97470

Wonderful care and communication each day!

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Megan M.
Sitter Profile Image: Heather A.
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Heather A.
from
$22
per visit
4.7 out of 5 stars
15 reviews
5 repeat clients
20 years of experience
Oakland, OR, 97462

Flexible and helpful with changes in our trip plans altering her drop-in schedule. Took great care of our kitty. We recommrnd her unreservedly!

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Gregory H.
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The median cost per night for pet sitting in Winchester is $23

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Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winchester on Rover as of Jun 2026 was about $23 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Winchester pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 12 pet sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Winchester.

Rover makes it easy to find Winchester pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 12 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.