House Sitting in Winchester

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Tracy C.
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Sitter Profile Image: Tracy C.
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1. Tracy C.

Let me be your second best
Charles Town, WV, 25414
17.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
8 repeat clients
from
$45
per night

Tracy took amazing care of my fur babies, 2 dogs and one cat and a fish tank. Tracy was super accommodating to my one dog who is terrified of fireworks. She walked them multiple times a day. Her communication was perfect, she sent pics often. My house was spotless when I got home and she had washed and dried the sheets for our bed. I highly recommend Tracy.

Sitter Profile Image: Katharina K.
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Sitter Profile Image: Katharina K.
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2. Katharina K.

Animals are everything!
Winchester, VA, 22602
3.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$50
per night

Kat did a fantastic job watching our dog over the weekend! She is kind, thoughtful, and knows a lot about dogs. She spent a lot of time with Wally and took him on plenty walks. Overall I see a high level of quality care, attention, and communication. I highly recommend Kat as a sitter!

Sitter Profile Image: Megan S.
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Sitter Profile Image: Megan S.
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3. Megan S.

Attentive, (big) dog lover
Stephens City, VA, 22655
6.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
7 repeat clients
from
$60
per night

Megan is an absolute treasure!! And that’s with a T not a P. Although she was also a pleasure to work with she is one of the most capable, friendly, caring, conscientious, pet sitters I have ever met. I will definitely use her again. I say treasure because she’s the sitter I would want again and again and again. 10/10 🥰🥰

Sitter Profile Image: Leonarda V.
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Sitter Profile Image: Leonarda V.
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4. Leonarda V.

Your pup’s best friend 🐾
Stephens City, VA, 22655
7.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
9 repeat clients
from
$60
per night

This was my first time using Rover and it was a great experience. My usual boarding facility was full over Thanksgiving and I had to scramble to find other accommodations. Leonarda agreed to come stay at my home and take care of my 2 large dogs (50+ pounds each). She provided references that gave glowing reviews so I decided to give it a shot. She seemed to really enjoy the dogs and I could tell they liked having her around. She sent me photos while I was away so I wouldn't miss them too much. I will 100% look for her help next time I travel.

Sitter Profile Image: Roxana N.
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Sitter Profile Image: Roxana N.
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5. Roxana N.

Dog lover!
Winchester, VA, 22601
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
8 reviews
3 repeat clients
from
$50
per night

Roxana took very good care of Allie for the week!

Sitter Profile Image: Ian D.
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Sitter Profile Image: Ian D.
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6. Ian D.

I love dogs like they are my family
Stephenson, VA, 22656
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$30
per night

Ian did a fabulous job caring for our dog Winston. Winston has severe separation anxiety and is usually pretty wound up when we’re not there, but he seemed to remain pretty calm while Ian was there. Will absolutely use again.

Sitter Profile Image: Abby F.
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Sitter Profile Image: Abby F.
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7. Abby F.

Compassionate and reliable sitter!
Winchester, VA, 22601
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$70
per night

Abby did a great job watching my energetic 3 year old black lab. Thank you so much.

Sitter Profile Image: Melissa Á.
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Sitter Profile Image: Melissa Á.
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8. Melissa Á.

Fun Sitter!
Winchester, VA, 22601
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$37
per night

Melissa was dedicated to get to know our super anxious dogs. She cleaned up, took out our trash and even did laundry while staying in our home with our 2 Aussies. Super detailed and gave plenty of updates.

Sitter Profile Image: Collin Q.
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Sitter Profile Image: Collin Q.
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9. Collin Q.

Forever dog lover
Winchester, VA, 22602
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$30
per night

Collin was prompt when responding to my text. He managed my dogs well and would send update pictures. Very responsible and respectful. Definitely would use again.

Sitter Profile Image: Chase R.
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Sitter Profile Image: Chase R.
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10. Chase R.

Furry, scaly, and feathery welcome!
Winchester, VA, 22602
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$35
per night

Chase did a great job watching my two dogs at my house. She sent me daily updates and took them for a walk. I will definitely hire again! Highly recommended

Sitter Profile Image: Julia Z.
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Sitter Profile Image: Julia Z.
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11. Julia Z.

Experienced
Winchester, VA, 22601
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$50
per night

She was so patient with our big dog and even played ball with him. It was so comforting to know our dog was being cared for as if we were there.

Sitter Profile Image: Steven F.
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Sitter Profile Image: Steven F.
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12. 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
15 reviews
7 repeat clients
from
$31
per night

Steven is so lovely with our 2 dogs and cat. They all love him. He’s very responsible and did a great job taking care of them and giving plenty of love and attention. Highly recommend!!

Sitter Profile Image: Alex H.
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Sitter Profile Image: Alex H.
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13. Alex H.

Animal Guru
Winchester, VA, 22601
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$48
per night

Alex did a great job taking care of our fur babies. He didn't hesitate to reach out to us if he had questions and kept us well informed how the pups were doing.

Sitter Profile Image: Michelle R.
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Sitter Profile Image: Michelle R.
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14. Michelle R.

Must Love Dogs
Stephens City, VA, 22655
5.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$60
per night

Michelle was incredible! She really helped us out in a bind last minute. Her communication was stellar, and my dogs felt so loved!

Sitter Profile Image: Claire Z.
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Sitter Profile Image: Claire Z.
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15. Claire Z.

The purr-fet pet sitter
Winchester, VA, 22601
1.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$55
per night

This was our first time with Rover, and I have to say, we picked the BEST dog sitter the first time! Claire was amazing! I knew from our initial meeting that she was the perfect sitter for our girls, and she absolutely was! We have two middle-aged, rescue, Bichon Frise girls and their "ways" can be a bit difficult for some, but Claire took it on, and we couldn't be happier! She is friendly and kind and patient. She sent us photos and updates from the beginning. I didn't worry one bit about the girls or the house for the three full days and two nights that we were gone! If I could give her MORE stars on Rover, I would! We have found our dog sitter!! Thank you Claire!!! :)

Sitter Profile Image: Mary M.
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Sitter Profile Image: Mary M.
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16. Mary M.

Hello!
Winchester, VA, 22601
0.6 mi. away
House Sitting
5.0 out of 5 stars
8 reviews
4 repeat clients
from
$35
per night

Mary was wonderful! She took care of Pippa for a week! I will definitely be asking her back. She kept me posted with pictures and videos. When the power flickered and caused the AC to go out, she tried troubleshooting, and then dealt with the electrician and HVAC tech. I felt very good wirh Mary yaking care of that and Pippa too!

Sitter Profile Image: Lydia M.
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Sitter Profile Image: Lydia M.
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17. Lydia M.

Trustworthy animal lover!
Winchester, VA, 22602
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$88
per night

Lydia stayed overnight with my 9 year old Teddy for 8 night and we will for sure be using her services again! She’s very trustworthy and sent pictures and videos of Teddy while we were gone to make us feel comfortable!

Sitter Profile Image: Sierra B.
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Sitter Profile Image: Sierra B.
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18. 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
1 review
from
$25
per night

About: I’ve been trusted on numerous occasions to take care of family pets of different breeds and species since I was 13. I have owned several fish, one guinea pig, and multiple cats. I absolutely adore every animal regardless of breed, species, or size! I’m currently working via popular food delivery apps, which means my schedule is highly flexible, so I’m always able to make my time work FOR YOU!! I always ensure that my furry friends feel safe and keep the more energetic ones engaged to prevent any possible destructive behavior! I can also read to the furry friends that aren’t quite as energetic as I know it helps calm their nerves should they be anxious!

Sitter Profile Image: Regina B.
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Sitter Profile Image: Regina B.
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19. Regina B.

Love all kinds of animals
Winchester, VA, 22601
2.6 mi. away
House Sitting, Dog Walking
5 years of experience
from
$20
per night

About: Well first of all, I’m a retired Corrections Officer of 25 yrs. I’ve always had a love for animals and their well being. And wanted to work with animals of all kinds.( Especially dogs). I am retired from corrections and have a lot of time on my hands. I would love to spend this free time working with animals. I have two dogs of my own and have always owned dogs and cats. I care for them with love and affection. While tending to their personal needs.

Sitter Profile Image: Alyssa F.
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Sitter Profile Image: Alyssa F.
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20. Alyssa F.

Lover of all animals & flexible!
Winchester, VA, 22601
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
6 repeat clients
from
$40
per night

Alyssa was an awesome sitter! My dog can be shy around new people and she did an amazing job getting my dog to warm up to her and she was excellent with sending updates and pictures! Will definitely use her again!!

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Winchester House Sitting ratings

Overall Rating:
5.0 out of 5 stars

House sitters in Winchester are rated on average 5 out of 5 stars based on 279 reviews.

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The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. 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 house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. 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 house sitters for your pets--and avoid the kennel.

House Sitting