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: Megan S.
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Sitter Profile Image: Megan S.
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1. 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
26 reviews
7 repeat clients
from
$60
per night
Profile image

Megan took care of my senior dog Reese without any issues. She kept me up to date with pictures and text messages. Reese seemed relaxed and rested when we got home versus going to a kennel. I highly recommend Megan for pet sitting and all services she provides.

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
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$40
per night
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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: Ian D.
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Sitter Profile Image: Ian D.
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3. 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
1 repeat client
from
$30
per night
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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: Melissa Á.
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Sitter Profile Image: Melissa Á.
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4. Melissa Á.

Fun Sitter!
Winchester, VA, 22601
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
7 repeat clients
from
$37
per night
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Melissa went above and beyond to make sure our dogs were well cared for, she gave constant updates, including photos, my house was in better shape than when I left it, and she did lots of extras to make sure I truly did not worry the entire weekend we were gone! Would highly recommend and hire again in a second!!

Sitter Profile Image: Leonarda V.
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Sitter Profile Image: Leonarda V.
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5. 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
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Leonard’s was wonderful! Her partner Jon who is also with Rover also stayed with our dogs. They were courteous, responsive and sent tons of picture updates. We had a great experience

Sitter Profile Image: Abby F.
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Sitter Profile Image: Abby F.
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6. 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
6 reviews
1 repeat client
from
$70
per night
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Abby did a great job watching my energetic 3 year old black lab. Thank you so much.

Sitter Profile Image: Collin Q.
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Sitter Profile Image: Collin Q.
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7. 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 very friendly with my pets. They really enjoyed him playing with them. He took great care of them. He had great communication with me the time I was away.

Sitter Profile Image: Steven F.
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Sitter Profile Image: Steven F.
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8. 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
16 reviews
7 repeat clients
from
$31
per night
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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: Carter J.
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Sitter Profile Image: Carter J.
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9. 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
4 reviews
from
$40
per night
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Carter did a fantastic job watching our 2 dogs and cat for the weekend. He kept us up to date and sent photos. They were well-tended and happy when we got back, and house was as we left it! Highly recommend Carter!

Sitter Profile Image: Roxana N.
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Sitter Profile Image: Roxana N.
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10. 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
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Roxana took very good care of Allie for the week!

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
2 repeat clients
from
$50
per night
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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: Chase R.
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Sitter Profile Image: Chase R.
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12. 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
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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: Claire Z.
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Sitter Profile Image: Claire Z.
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13. 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
Profile image

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: Sierra B.
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Sitter Profile Image: Sierra B.
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14. 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: Alex H.
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Sitter Profile Image: Alex H.
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15. 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
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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: Catherine H.
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Sitter Profile Image: Catherine H.
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16. Catherine H.

I am experienced with all ages!
Winchester, VA, 22602
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$50
per night
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Catherine is absolutely phenomenal. I could not recommend her enough. She handled an awful situation with our door key breaking. Our dogs were so well taken care of and extremely happy when we returned. I completely trust her with my dogs!

Sitter Profile Image: Michelle R.
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Sitter Profile Image: Michelle R.
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17. 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
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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: Mary M.
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Sitter Profile Image: Mary M.
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18. 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
Profile image

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: Emily H.
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Sitter Profile Image: Emily H.
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19. Emily H.

Young professional who loves pets
Winchester, VA, 22601
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$150
per night

Emily is awesome. A true animal person who will love and pamper your pet. She is very passionate and caring and your pet will absolutely love Emily.

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
Profile image

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.

Rover also offers House Sitting in:

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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