Pet Sitting in Winchester

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Sierra B.
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Sitter Profile Image: Sierra B.
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1. Sierra B.

Energetic Animal Lover
Winchester, VA, 22602
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$15
per visit
Profile image

Awesome communication and taking care of our pup!

Sitter Profile Image: Kimberly B.
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Sitter Profile Image: Kimberly B.
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2. Kimberly B.

Provides loving and engaging care
Winchester, VA, 22601
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
189 reviews
67 repeat clients
from
$22
per visit
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Kimberly went very very above and beyond in taking care of our cat during a winter storm. She is wonderful — I can’t recommend her more highly. I will book again soon!

Sitter Profile Image: Amanda L.
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Sitter Profile Image: Amanda L.
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3. Amanda L.

I treat every fur baby like my own!
Winchester, VA, 22603
4.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
7 repeat clients
from
$18
per visit
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Amanda is fantastic with our girl Bella! We can always trust that Bella will be taken care of. She plays with her, shows her love and sends lots of pictures. We are very lucky to have her!

Sitter Profile Image: Steven F.
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Sitter Profile Image: Steven F.
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4. Steven F.

Your furbaby's vacation home
Winchester, VA, 22602
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
8 repeat clients
from
$15
per visit
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Steven showed up on time and even cleaned up a bit of a mess my dogs had made! Will definitely book again when I need a drop in!

Sitter Profile Image: Cora D.
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Sitter Profile Image: Cora D.
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5. Cora D.

Those paws were made for walkin'
ClearBrook, VA, 22624
5.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$20
per visit
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Once again, Cora to the rescue!!

Sitter Profile Image: Kyla P.
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Sitter Profile Image: Kyla P.
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6. Kyla P.

Stay-at-home dog mom ❤️
Winchester, VA, 22601
1.6 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
20 repeat clients
from
$20
per visit
Profile image

Kyla was wonderful with Peppa despite rain and Peppa not being a fan of that. 😁. Yiu can tell jKyla enjoys her work! Peppa loved her. 🥰. I appreciated her timely visits and pics sent to show Peppa being so happy.

Sitter Profile Image: Bridgette M.
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Sitter Profile Image: Bridgette M.
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7. Bridgette M.

Years experience - dog LOVER!
Winchester, VA, 22602
3.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
12 repeat clients
from
$25
per visit
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Bridgette was SO incredibly good with my two dogs and cat. Not only did she send me FANTASTIC pictures during their play time outside, but wrote a really detailed summary of their time together. My older GSD Max isn’t the quickest to befriend strangers, but Bridgette’s expertise training and working with dogs of all sizes proved to be extremely successful. I will definitely continue to use Bridgette in the future, and HIGHLY recommend that you reach out to here as well!!

Sitter Profile Image: Corbin B.
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Sitter Profile Image: Corbin B.
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8. Corbin B.

Just a girl who loves animals!
Winchester, VA, 22601
0.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
12 repeat clients
from
$15
per visit
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Another wonderful visit by Corbin! We are so blessed to have found her! (Dixie & Tessa say thank you, too! Especially because you put up with all our mommies notes & texts hehehe!!) 🥰

Sitter Profile Image: Brooke H.
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Sitter Profile Image: Brooke H.
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9. Brooke H.

WFH Pet Lover
Winchester, VA, 22601
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$15
per visit

Brooke is very loving and caring of our staffy mix who loves to cuddle and play fetch. Animals always seem to love her when she walks in the room whether they’re cats or dogs. You’d be lucky to have her take care of your pet when you’re not able to!

Sitter Profile Image: Carter J.
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Sitter Profile Image: Carter J.
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10. Carter J.

College kid that loves dog walks!
Winchester, VA, 22601
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$18
per visit
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Carter has been wonderful to our four dogs while we were away. We could not have asked for better treatment of them. He gave them the time and attention they deserve. We would love to have him back again.

Sitter Profile Image: Stefanie S.
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Sitter Profile Image: Stefanie S.
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11. Stefanie S.

Fervent pet care provider for 15+yr
Winchester, VA, 22601
2.8 mi. away
House Sitting, Drop-In Visits
3 reviews
from
$15
per visit

Stefanie is always so great with my big dog Mac! She is always so thorough with updates and his care as he’s a bit needy. Couldn’t recommend her more!

Sitter Profile Image: Kathy G.
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Sitter Profile Image: Kathy G.
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12. Kathy G.

Love having snuggle buddies
Winchester, VA, 22601
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
42 reviews
14 repeat clients
from
$20
per visit
Profile image

Kathy was so responsive and reliable! She took great care of our dog and gave detailed info as well as pictures after all of her visits! we will definitely use her again ☺️

Sitter Profile Image: Kyle R.
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Sitter Profile Image: Kyle R.
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13. Kyle R.

I care because you care.
Winchester, VA, 22601
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5 years of experience
from
$13
per visit

About: I've helped care for our family pets (dog and cat) since I was 12. Since 2023, I've cared for my own cat and dog. I have experience dealing with anxious and reactive cats/dogs (my pets). I currently have an open availability as I am between jobs. I am willing to discuss any schedule needs. I am willing to stay overnights, and visit early or late hours as needed. I will take notes to insure care is exactly as you need it. I am comfortable feeding and medicating (non-IV) as needed. I am comfortable with all types of play, from gentle playing to fast-paced, high energy play.

Sitter Profile Image: Melissa Á.
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Sitter Profile Image: Melissa Á.
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14. Melissa Á.

Fun Sitter!
Winchester, VA, 22601
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
9 repeat clients
from
$20
per visit
Profile image

Melissa was amazing!! Our cats loved her! She was so flexible with our requests, went above and beyond in her care, and had amazing communication! We were so blessed to have such a loving person like her caring for our babies. Melissa put our minds at ease which allowed us to better enjoy our vacation. Thank you for everything and we will be booking you again for our next trip!!

Sitter Profile Image: Laís R.
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Sitter Profile Image: Laís R.
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15. Laís R.

Can I get paid to have fun?
Winchester, VA, 22601
0.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
8 repeat clients
from
$20
per visit
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Lais took great care of our baby!

Sitter Profile Image: Shaghayegh H.
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Sitter Profile Image: Shaghayegh H.
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16. Shaghayegh H.

Rover 101
Your bestie will have lots of FUN
Winchester, VA, 22602
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
154 reviews
41 repeat clients
from
$25
per visit
Profile image

We had a family emergency and had to leave our Dog Piff at home and Shaghayegh was amazing! She really went above and beyond for my family and made sure our dog was taken care off. She let us know before and after she left and always sent pictures everyday! I would 100% use her again!

Sitter Profile Image: Meaghan G.
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Sitter Profile Image: Meaghan G.
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17. Meaghan G.

Ready to meet your furry friend!
Winchester, VA, 22601
0.6 mi. away
Drop-In Visits, Dog Walking
20 years of experience
from
$20
per visit

About: Since I was 7 years old, the responsibility of taking care of a young puppy was my passion and purpose, igniting a lifelong commitment to nurturing and understanding dogs' needs with love and dedication. Throughout my teenage years, I took care of pets of all ages. Whether it was giving medication to the elderly pups or going on extra-long walks to expend their boundless puppy energy, I have always prioritized their well-being and happiness above all else. What sets me apart as a dog sitter is my comprehensive experience in handling dogs of all ages and needs. Whether it's training energetic puppies or providing gentle care for senior dogs, I bring a deep understanding of canine behavior and individualized attention to ensure every furry friend feels safe, loved, and well-cared for. With my recent availability, I can dedicate ample time each day to ensure pets receive the attention, exercise, and care they deserve. Whether it's early morning walks, midday play sessions, or evening cuddle time, I prioritize their well-being as a central part of my daily schedule. When caring for pets in clients' homes, I focus on maintaining their routines and familiar surroundings to minimize stress. I ensure timely feeding, regular walks or outdoor activities, and lots of interaction and companionship to keep them happy and engaged. I am diligent about following any special instructions provided by the client, such as administering medication or adhering to specific training techniques, to ensure consistency and comfort for their pets while they're away.

Sitter Profile Image: Christa K.
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Sitter Profile Image: Christa K.
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18. Christa K.

Nothing more true than a dog's love
Winchester, VA, 22601
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
9 repeat clients
from
$15
per visit
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Thank you so much! Christa was great and made sure my dogs were taken care of. Great pictures! And thorough. I will book with Christa again for sure!

Sitter Profile Image: Alex T.
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Sitter Profile Image: Alex T.
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19. Alex T.

Huge Dog Lover
Winchester, VA, 22601
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$20
per visit

I cannot recommend Alex enough! My sweet Brutus has learned to love Alex as his own master. At first I was weary how much more he loved her than me, but now I couldn't be happier. She takes such good care of my snorty bulldog. Alex is my go to for any time I need help. She is there to walk him, play with him, feed him and love him. She came highly recommended to me by my grandmother, who also swears by her. She is now my entire family's one and only pet sitter. Although she specializes in dogs, she has taken care of all of the animals in our family - to list a few, cat, guinea pig, python and fish (we are a family of animal lovers!) In conclusion, ALEX IS THE BEST.

Sitter Profile Image: Alex H.
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Sitter Profile Image: Alex H.
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20. Alex H.

PetSmart Dog Trainer
Winchester, VA, 22601
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
2 repeat clients
from
$14
per visit
Profile image

We rehired Alex to look after our big dog Rocky again for a week while we celebrated our anniversary. He did an amazing job and kept us updated with pictures of Rocky and rocky looked like he was having a blast in all the pictures. Alex played fetch with him in our yard daily and made sure Rocky had enough toys to play with. We came home to a happy dog and we are very grateful we could celebrate our anniversary without worrying about how Rocky was faring back home thanks to Alex!

Search Map

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Winchester:

The next time you head out of town and need someone to take care of your pets - and check in on you home - turn to Rover. It's easy to find a loving pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover - it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy pet sitters and avoid the kennel.

Drop-In Visits