House Sitting in Winchester

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Top rated Winchester house sitters

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Sitter Profile Image: Alexsys T.
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Alexsys T.
Star Sitter
from
$55
per night
5 out of 5.0 stars
74 reviews
27 repeat clients
7 years of experience
Clear Brook, VA, 22624

Alexsys was wonderful with Bailey! When I had a recent family emergency with my daughter going into labor three weeks early, I had town quickly. Alexsys jumped right in and took great care of Bailey, sending pictures and updates that really helped me feel comfortable leaving my furbaby. I would definitely book her again!

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Cynthia M.
Sitter Profile Image: Charissa L.
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Charissa L.
from
$30
per night
5 out of 5.0 stars
4 reviews
15 years of experience
Winchester, VA, 22602

Charissa was amazing, daily photos of our cat, she was well taken care of and the communication was impeccable. Would highly recommend and use again.

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Giovanna C.
Sitter Profile Image: Kathy G.
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Kathy G.
Star Sitter
from
$70
per night
5 out of 5.0 stars
55 reviews
17 repeat clients
30 years of experience
Winchester, VA, 22601

Kathy is a true gem. We had complete peace of mind while she house sat our three Lab rescues. Kathy is dependable, communicative, and takes care of your house and pets like they are her own. We will absolutely be booking her again.

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Jessica F.
Sitter Profile Image: Steven F.
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Steven F.
from
$31
per night
5 out of 5.0 stars
25 reviews
10 repeat clients
15 years of experience
Winchester, VA, 22602

Steven is amazing! Reliable, communicative, and very thoughtful. Our cats were comfortable and immediately warmed to him. I would enthusiastically recommend Steven to anyone who needs great pet care.

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Kimberly S.
Sitter Profile Image: Alex K.
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Alex K.
from
$45
per night
5 out of 5.0 stars
18 reviews
6 repeat clients
10 years of experience
Winchester, VA, 22602

Alex really helped me out short notice and over a holiday!! She provided personalized care and is very knowledgeable. I knew my high-energy pup was in good hands :) i loved the photos / vid updates — will def reach out again!

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Emily A.
Sitter Profile Image: Sadie S.
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Sadie S.
from
$40
per night
5 out of 5.0 stars
12 reviews
1 repeat client
5 years of experience
Winchester, VA, 22601

About: My name is Sadie. I am an 20 year-old, third year, at Shenandoah University. I love hanging around dogs, cats, or honestly any animal. I have been exposed to all types of animals from farm to regular housepets. I was raised living with a cat and taking care of chickens. I also would help out neighbors with watching their pets; started doing so around the age of 12. I have quite a few experiences under my belt with dogs ranging from 5 month olds through veterans. My dog is an American Pitbull Terrier and is now 3 years old. I love him and any animal I am responsible for with all I have. When I am home from school, I am more than likely open to any schedule. Most likely what works for you, will work for me! As of right now, I do have another part-time, low hour job and internship. Even with those two, I have plenty of free time to come help you with your pets! Your pets will be cared for by me just as much as you do for them. I am a hard worker who will always give 110% into caring for your pets. Whatever you ask of me to do, I will do my best to complete to your and your pets' satisfaction. I also will provide you with pictures and updates whenever your pets and I do anything.

Sitter Profile Image: Shannon B.
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Shannon B.
from
$55
per night
5 years of experience
Winchester, VA, 22602

About: Have had dogs all my life. Love them and they love me! Long walks and dog parks, if allowed, plus all the belly rubs and treats! Currently nannying and going back to school. Have a very flexible schedule and available at most times during the day and evening for walks or drop ins. I like to meet your fur babies first to make sure it’s a good fit for both of us. Discuss behavior and tendencies. Happy to go on walks, let them out, hangout and play.

Sitter Profile Image: Maddie E.
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Maddie E.
from
$40
per night
5 out of 5.0 stars
3 reviews
1 repeat client
20 years of experience
Stephens City, VA, 22655

Maddie was so sweet, reliable, and took great care of our pups. We will absolutely be using her again!

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Jessica S.
Sitter Profile Image: Carse R.
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Carse R.
from
$35
per night
5 out of 5.0 stars
7 reviews
1 repeat client
40 years of experience
Stephens City, VA, 22655

Carse provided terrific care for our pups!

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Ruth D.
Sitter Profile Image: Roxana N.
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Roxana N.
from
$50
per night
5 out of 4.2 stars
8 reviews
3 repeat clients
4 years of experience
Winchester, VA, 22601

Roxana took very good care of Allie for the week!

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Amanda F.
Sitter Profile Image: Ashley R.
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Ashley R.
from
$31
per night
5 out of 5.0 stars
5 reviews
7 years of experience
Winchester, VA, 22601

Ashley did an outstanding job of taking care of our Pupper while we gone for the weekend. She gave detailed updates throughout those couple of days and sent us photos! I highly recommend her services if you need someone professional, responsible and will take of your pups like her own.

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Troy M.
Sitter Profile Image: Mary M.
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Mary M.
from
$40
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
2 years of experience
Winchester, VA, 22601

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!

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Lynda M.
Sitter Profile Image: Sabrin W.
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Sabrin W.
from
$50
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
16 years of experience
Winchester, VA, 22602

Sabrin was great! She typically doesn’t do large size dogs, but she decided to meet mine and he loves her. My Pomsky is usually stressed and can be standoff but she went straight to Sabrin and begged for attention. My cat (willow) who usually stays away from strangers but came out to greet Sabrin and even allowed Sabrin to pick her up. I was very pleased with Sabrin and how flexible she was with my sudden change in vacation days/times. I highly recommend and will be asking for her services again! Thank you Sabrin:)

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Ashlee C.
Sitter Profile Image: Carter J.
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Carter J.
from
$90
per night
5 out of 5.0 stars
8 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

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!

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Mary H.
Sitter Profile Image: Stefany P.
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Stefany P.
from
$60
per night
5 out of 5.0 stars
2 reviews
5 years of experience
Winchester, VA, 22602

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)

Sitter Profile Image: Gabe E.
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Gabe E.
from
$60
per night
5 out of 4.5 stars
6 reviews
10 years of experience
Winchester, VA, 22601

Gabe did a great job!

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Alyssa L.
Sitter Profile Image: Maribeth T.
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Maribeth T.
from
$35
per night
5 out of 4.3 stars
10 reviews
2 repeat clients
12 years of experience
Winchester, VA, 22601

About: -About Me- I've had 10+ years experience in doggy care! I've delivered puppies at the age of 15 and worked close to my parents and their vet business all my life. I love dogs of all sizes and breeds. Caring for them is second nature for me :) I've fostered several dogs over the past three years. -My Motto- I can offer you relief knowing that your pup is being taken care of by an experienced and genuinely loving caretaker! - Doggies Love Excercise - On our walk I will provide your pup with some workouts and toys to ensure he/she has the best walk of their life! I am very honored and excited to get to know your fur baby! Book your appointment today! i’m currently working fully remote so rest assured you pet will be 100% taken care of 100% of the time. We have an amazing dog park near by and lots of trails for your fur babies to explore! i have many nature trails and a doggy park nearby so you can rest peacefully knowing your pup will definitely get some exercise under my care, fed on their regular schedule and given all the pets they want.

Sitter Profile Image: Claire Z.
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Claire Z.
from
$65
per night
5 out of 5.0 stars
6 reviews
1 repeat client
4 years of experience
Winchester, VA, 22601

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!!! :)

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Kimberly C.
Sitter Profile Image: Alex H.
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Alex H.
from
$52
per night
5 out of 5.0 stars
20 reviews
8 repeat clients
10 years of experience
Winchester, VA, 22601

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.

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Suzette N.
Sitter Profile Image: Taylor S.
Verified Background Check
Taylor S.
from
$50
per night
5 years of experience
Winchester, VA, 22601

About: I love working with animals! I have years of experience caring for animals between pet sitting and shelter work. I have experience bathing, grooming pets, determining daily food portions, walking dogs, providing companionship, and administering medicine. I find caring and being around animals on a regular basis to be very rewarding. I work full-time Monday-Thursday. I am available as early as 6:00am-5:00pm Friday, Saturday, and Sunday. I can be flexible to you and your pet/pets needs. I will ensure your pet/pets receive love, affection, and adequate time will be given for their care. Depending upon your pet/pets needs, long walks, play time, ect.

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Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check
Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check

1. Alexsys T.

Star Sitter
Everything for your pet under 1woof
Clear Brook, VA, 22624
3.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
5 out of 5.0 stars
74 reviews
27 repeat clients
Profile image

Alexsys was wonderful with Bailey! When I had a recent family emergency with my daughter going into labor three weeks early, I had town quickly. Alexsys jumped right in and took great care of Bailey, sending pictures and updates that really helped me feel comfortable leaving my furbaby. I would definitely book her again!

Availability updated today
Sitter Profile Image: Charissa L.
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Sitter Profile Image: Charissa L.
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2. Charissa L.

Animal lover happy to help!
Winchester, VA, 22602
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
4 reviews
Profile image

Charissa was amazing, daily photos of our cat, she was well taken care of and the communication was impeccable. Would highly recommend and use again.

Availability updated 7 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Kathy G.
Verified Background Check
Sitter Profile Image: Kathy G.
Verified Background Check

3. Kathy G.

Star Sitter
Love having snuggle buddies
Winchester, VA, 22601
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 5.0 stars
55 reviews
17 repeat clients
Profile image

Kathy is a true gem. We had complete peace of mind while she house sat our three Lab rescues. Kathy is dependable, communicative, and takes care of your house and pets like they are her own. We will absolutely be booking her again.

Availability updated today
Sitter Profile Image: Steven F.
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Sitter Profile Image: Steven F.
Verified Enhanced Background Check

4. Steven F.

Your furbaby's vacation home
Winchester, VA, 22602
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$31
per night
5 out of 5.0 stars
25 reviews
10 repeat clients
Profile image

Steven is amazing! Reliable, communicative, and very thoughtful. Our cats were comfortable and immediately warmed to him. I would enthusiastically recommend Steven to anyone who needs great pet care.

Availability updated 22 days ago
Sitter Profile Image: Alex K.
Verified Enhanced Background Check
Sitter Profile Image: Alex K.
Verified Enhanced Background Check

5. Alex K.

I love taking care of all animals!
Winchester, VA, 22602
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
18 reviews
6 repeat clients
Profile image

Alex really helped me out short notice and over a holiday!! She provided personalized care and is very knowledgeable. I knew my high-energy pup was in good hands :) i loved the photos / vid updates — will def reach out again!

Availability updated 10 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Sadie S.
Verified Enhanced Background Check
Sitter Profile Image: Sadie S.
Verified Enhanced Background Check

6. Sadie S.

Everything your pet needs
Winchester, VA, 22601
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
12 reviews
1 repeat client

Sadie has been wonderful to work with, taking care of our fur babies. She is super reliable and trustworthy. She listens to our needs & instructions and asks questions to ensure we both are on the same page. She communicates throughout the "sitting" period keeping us informed of our fur babies well-being or challenges that may arise. And...I love the photos of her and the babies having fun. Sadie is the best!!

Availability updated 42 days ago
Sitter Profile Image: Shannon B.
Verified Enhanced Background Check
Sitter Profile Image: Shannon B.
Verified Enhanced Background Check

7. Shannon B.

Dog Lover
Winchester, VA, 22602
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
1 review

Shannon is the absolute best. Our entire family is pretty sure our dog Scott loves her more than any of us lol. She’s very dependable and she’s so great with Scott. She’s our first call if we have to go out of town and we need someone who will take incredible care of our dog, because we know she loves him as much as we do.

Availability updated 2 days ago
Sitter Profile Image: Maddie E.
Verified Enhanced Background Check
Sitter Profile Image: Maddie E.
Verified Enhanced Background Check

8. Maddie E.

Experienced with & love all breeds!
Stephens City, VA, 22655
6.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
3 reviews
1 repeat client
Profile image

Maddie was so sweet, reliable, and took great care of our pups. We will absolutely be using her again!

Availability updated 2 days ago
Sitter Profile Image: Carse R.
Verified Enhanced Background Check
Sitter Profile Image: Carse R.
Verified Enhanced Background Check

9. Carse R.

Animal Lover and Cat Whisperer
Stephens City, VA, 22655
5.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Carse provided terrific care for our pups!

Availability updated 4 days ago
Sitter Profile Image: Roxana N.
Verified Enhanced Background Check
Sitter Profile Image: Roxana N.
Verified Enhanced Background Check

10. Roxana N.

Dog lover!
Winchester, VA, 22601
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.2 stars
8 reviews
3 repeat clients
Profile image

Roxana took very good care of Allie for the week!

Availability updated over 1 year ago
Sitter Profile Image: Ashley R.
Verified Enhanced Background Check
Sitter Profile Image: Ashley R.
Verified Enhanced Background Check

11. Ashley R.

Pawfect day for a walk!!
Winchester, VA, 22601
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$31
per night
5 out of 5.0 stars
5 reviews
Profile image

Ashley did an outstanding job of taking care of our Pupper while we gone for the weekend. She gave detailed updates throughout those couple of days and sent us photos! I highly recommend her services if you need someone professional, responsible and will take of your pups like her own.

Availability updated 6 days ago
Sitter Profile Image: Mary M.
Verified Enhanced Background Check
Sitter Profile Image: Mary M.
Verified Enhanced Background Check

12. Mary M.

Hello!
Winchester, VA, 22601
0.1 mi. away
House Sitting, Drop-In Visits
from
$40
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
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!

Availability updated today
Sitter Profile Image: Sabrin W.
Verified Enhanced Background Check
Sitter Profile Image: Sabrin W.
Verified Enhanced Background Check

13. Sabrin W.

Safe, Loving Care for Your Pet!
Winchester, VA, 22602
3.2 mi. away
House Sitting, Drop-In Visits
from
$50
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
Profile image

Sabrin was great! She typically doesn’t do large size dogs, but she decided to meet mine and he loves her. My Pomsky is usually stressed and can be standoff but she went straight to Sabrin and begged for attention. My cat (willow) who usually stays away from strangers but came out to greet Sabrin and even allowed Sabrin to pick her up. I was very pleased with Sabrin and how flexible she was with my sudden change in vacation days/times. I highly recommend and will be asking for her services again! Thank you Sabrin:)

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Carter J.
Verified Enhanced Background Check
Sitter Profile Image: Carter J.
Verified Enhanced Background Check

14. Carter J.

College kid that loves dog walks!
Winchester, VA, 22601
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$90
per night
5 out of 5.0 stars
8 reviews
1 repeat client
Profile image

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!

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Stefany P.
Verified Background Check
Sitter Profile Image: Stefany P.
Verified Background Check

15. Stefany P.

Flexible&friendly pet care services
Winchester, VA, 22602
2.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
2 reviews

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)

Availability updated today
Sitter Profile Image: Gabe E.
Verified Enhanced Background Check
Sitter Profile Image: Gabe E.
Verified Enhanced Background Check

16. Gabe E.

Animal loving professional
Winchester, VA, 22601
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.5 stars
6 reviews
Profile image

Gabe did a great job!

Availability updated yesterday
Sitter Profile Image: Maribeth T.
Verified Enhanced Background Check
Sitter Profile Image: Maribeth T.
Verified Enhanced Background Check

17. Maribeth T.

Fur baby specialist!
Winchester, VA, 22601
0.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 4.3 stars
10 reviews
2 repeat clients

Maribeth is one of the most wonderful people to come across when it comes to dog care. You can definitely tell she has a passion for animals. Her presence makes you feel comfortable and relieved knowing you can leave your dog with someone so trusting. She really treats your dog like family, thank you Maribeth you rock !!

Availability updated 15 days ago
Sitter Profile Image: Claire Z.
Verified Enhanced Background Check
Sitter Profile Image: Claire Z.
Verified Enhanced Background Check

18. Claire Z.

The purr-fet pet sitter
Winchester, VA, 22601
1.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$65
per night
5 out of 5.0 stars
6 reviews
1 repeat client
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!!! :)

Availability updated 9 days ago
Sitter Profile Image: Alex H.
Verified Enhanced Background Check
Sitter Profile Image: Alex H.
Verified Enhanced Background Check

19. Alex H.

Accredited Dog-Trainer at PetSmart
Winchester, VA, 22601
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$52
per night
5 out of 5.0 stars
20 reviews
8 repeat clients
Profile image

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.

Availability updated yesterday
Sitter Profile Image: Taylor S.
Verified Background Check
Sitter Profile Image: Taylor S.
Verified Background Check

20. Taylor S.

Animal Lover
Winchester, VA, 22601
0.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 years of experience

About: I love working with animals! I have years of experience caring for animals between pet sitting and shelter work. I have experience bathing, grooming pets, determining daily food portions, walking dogs, providing companionship, and administering medicine. I find caring and being around animals on a regular basis to be very rewarding. I work full-time Monday-Thursday. I am available as early as 6:00am-5:00pm Friday, Saturday, and Sunday. I can be flexible to you and your pet/pets needs. I will ensure your pet/pets receive love, affection, and adequate time will be given for their care. Depending upon your pet/pets needs, long walks, play time, ect.

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house 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.

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