House Sitting in Winchester

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

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
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Sitter Profile Image: Lucy S.
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Sitter Profile Image: Lucy S.
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1.

Lucy S.

Animal lover artist with a havapoo
Reservorir, Lexington, KY, 40502
15.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$70
per night

As soon as my Sadie met Lucy, I knew we had a good fit! Lucy's easy demeanor had Sadie happily engaged. Lucy texted daily, with pictures, letting us know all was well. I recommend her and would use her again!

Sitter Profile Image: Savannah O.
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Sitter Profile Image: Savannah O.
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2.

Savannah O.

Animal lover/caretaker
Winchester, KY, 40391
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
9 repeat clients
from
$50
per night

Savannah has been great to book with the past two times we’ve had her watch our pups. So glad to have someone in the area and reliable to watch our dogs when we’re out of town!

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Sitter Profile Image: Arian R.
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Sitter Profile Image: Arian R.
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3.

Arian R.

Rover 101
Air's Home Care
Lexington, KY, 40502
16.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
44 reviews
15 repeat clients
from
$100
per night

Arian stayed with Gracie for 8 nights while we were away. She quickly bonded with her and they fell into a very comfortable routine! In fact, we think Gracie might just prefer Arian over us. Phenomenal communication, tons of pictures, and no issues. I would highly recommend Arian without hesitation!

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Sitter Profile Image: Dani K.
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Sitter Profile Image: Dani K.
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4.

Dani K.

Rover 101
My goal = you're animals happy!!!
Kenawood-Rockwood, LEXINGTON, KY, 40505
15.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
275 reviews
115 repeat clients
from
$80
per night

Dani was so wonderful. She housesat for us and our German shepherd. Dolly took to her right away at the meet and greet. Dani always sent daily updates with lots of pictures that made me feel comforted while away.

Sitter Profile Image: Chay H.
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Sitter Profile Image: Chay H.
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5.

Chay H.

I love making pets happy!
Duncan Park, Lexington, KY, 40508
17.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
108 reviews
53 repeat clients
from
$35
per night

Chay stayed with my cat while I was away for a few nights and took amazing care of her. She went above and beyond and even left a cute treat for my cat!! Will definitely rebook with her in the future!

Sitter Profile Image: Gisela A.
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Sitter Profile Image: Gisela A.
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6.

Gisela A.

Fur Babies are the Bestttt!!!!!
Richmond, KY, 40475
18.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
19 years of experience
from
$63
per night

About: I have had animals my whole life and love them!! I currently have 2 dogs and 1 cat. I care for them along with many animals of my friends and family. I have a wide variety of experience from all sizes, breeds, and ages. I promise to love your animal just as they were mine:) I am a nursing student at EKU and I am just looking for something that will allow me to balance my school schedule as well. I have a pretty open schedule except for Tuesday’s and Thursdays which I am not available from 8:00am-4:00pm due to classes. I am not able to be at home with my animals so why not accompany the ones around me😊 I pretty much do whatever the client wants me to do or what the animal is used to. I do not crate my animals at home due to someone always being in the household with them but am understanding of any demands or routines.

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Sitter Profile Image: Ella T.
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Sitter Profile Image: Ella T.
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7.

Ella T.

Love all big and small dogs!
Southern Park, Lexington, KY, 40508
18.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4 reviews
from
$55
per night

Ella has been my dogsitter since my first dog was a puppy. He is now 3 years old and I have a 1 year old dog of the same breed and she is the only one I trust to take care of them. They are high energy dogs, which Ella handles with ease, and they absolutely LOVE when she is there, and they are actually sad when she leaves. Ella is always punctual, great at following directions, and extremely trustworthy. She is the biggest animal lover and everyone that she has worked for loves her. You can relax knowing your pets will be extra loved and taken care of by Ella. I recommend her to everyone I know! FIVE STARS.

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Sitter Profile Image: Madison M.
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Sitter Profile Image: Madison M.
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8.

Madison M.

Hi there!
Lexington, KY, 40515
11.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
10 years of experience
from
$40
per night

About: Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching/taking care of dogs for around 8 years and I love it! I currently work full time at a thoroughbred farm in Nicholasville! When I house sit, my typical routine is to get up around 7, take care of all the fur babies and head to work! When my lunch break comes, around 12, I head back and hang out and play with all of the animals until I have to go back to work around 1. Then around 3:30/4 I head home for the night :) I have a fenced in backyard that is shaded by trees! All the dogs that I have watched seemed to love hanging out in the backyard!

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Sitter Profile Image: Jason P.
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Sitter Profile Image: Jason P.
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9.

Jason P.

Reliable and attentive petsitter.
Mount Sterling, KY, 40353
13.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$35
per night

Jason has cared for our 3 dogs (retriever and two chihuahuas - 1 senior with certain challenges) for over 2 years as well as my mother’s dog, and my mother-in-law’s group of 6; he has done walks for us, pet sitting, and a few overnight care stays. He is attentive, follows instructions well, loves to play and engage with them, and overall is genuinely loving and intuitive with them as if they were his own! If you want to know your fur baby is in good hands with someone reliable, look no further!

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Sitter Profile Image: Abby W.
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Sitter Profile Image: Abby W.
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10.

Abby W.

Lexington’s Wannabe Dog Mom
Chevy Chase-Ashland Park, Lexington, KY, 40502
17.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$40
per night

Abby was awesome. Are pet is a bit older and she was great at giving his meds and caring for Tyler. Shes super great at texting back and stayed at house which she left in perfect order. Definitely will book Abby again

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Sitter Profile Image: Miranda M.
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Sitter Profile Image: Miranda M.
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11.

Miranda M.

Ready to Pamper Your Pawsome Pals!
Lexington, KY, 40515
14.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
7 repeat clients
from
$100
per night

Miranda did a fantastic job with my 3 pets. My pets all have very different needs so I always like someone to stay at the house, primarily for my senior dog and cat. My cat came out during my trip away and even let Miranda pet her, which is high praise! I have a high energy Aussie that Miranda was able to bring on walks and do mental work with to wear her out. I truly appreciate being able to go out of town and not worry about my girls. As a bonus, she watered my plants and my house was cleaner than when I left! I would highly recommend Miranda for any pet personality and needs.

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Sitter Profile Image: chloe k.
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Sitter Profile Image: chloe k.
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12.

chloe k.

I would love to pet sit for you!!!!
Winchester, KY, 40391
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 years of experience
from
$60
per night

About: I love all kinda of animals! Every time I see a dog I always ask to pet the dog! I feel like I have a special connection with animals, they’re so loving and always understand what you’re going through. Animals show the love they are given. I currently work at tjmaxx, but it’s only part time so a couple hours a week, I also do online school work, but I am always available! I love to hangout with my pets! My family currently has four dogs right now, we just took one in off of the street so he could get proper care. We also feed the outside cats (sometimes I sneak them in) just so they can get extra love! But I mostly cuddle with them on the porch while I read my book.

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Sitter Profile Image: Shelby B.
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Sitter Profile Image: Shelby B.
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13.

Shelby B.

Loving Care When You're Not There
Lexington, KY, 40509
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
104 reviews
44 repeat clients
from
$250
per night

We found Shelby on Rover after a friend had suggested using the site for our little rescue kitten, Tony. I was nervous about leaving him, albeit for less than a week but any fears or doubts I'd had were immediately erased when I met Shelby. She is so obviously a kind a gentle soul with an affinity for animals. On my way to drop Tony off he unfortunately had a nervous 'accident' in his carrier and so I was dreading arriving and having to leave both he and his carrier in a messy condition, but Shelby was not phased at all and calmly said she would take care it. While we were away on our trip we had constant updates, photos and videos of Tony playing with the other pets as well as with Shelby's little boy. This was an absolute pleasure and I felt relaxed and revealed the whole time knowing that Tony was being well taken care of as well as him having a great time. My only worry was that he might not want to come home when we went to pick him up! We will definitely be using Shelby again in the future :)

Sitter Profile Image: Dina J.
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Sitter Profile Image: Dina J.
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14.

Dina J.

Animal lover seeks fun furry friend
Lexington, KY, 40509
14.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
68 reviews
20 repeat clients
from
$20
per night

Dina is one of the BEST!!! Overall great person and you could instantly tell that she has a genuine care for the animals that she is around and taking care of. As a pet owner herself, she gets how difficult it is to leave the fur babies and made us feel at ease leaving them in her care. Dina sent regular updates and pictures throughout the stay which we LOVED!!! She was extremely accommodating and went above and beyond! We would book Dina again in a heartbeat as long as her availability allows (I know she is popular and rightfully so)!!! She also took great care of our home while we were away and we returned to our home as clean or maybe even a little cleaner than when we left it. Dina is fantastic and we would definitely recommend her to anyone asking.

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Sitter Profile Image: Jessica A.
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Sitter Profile Image: Jessica A.
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15.

Jessica A.

Tail-Wagging Care
Lexington, KY, 40509
14.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$27
per night

Jessica is one of maybe two people who: A) I trust with my dog for long periods of time and B) loves my dog as much as I do. Also she sends pics of the pup while I'm out of town which helps my anxiety a ton. 11/10

Sitter Profile Image: Bianca G.
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Sitter Profile Image: Bianca G.
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16.

Bianca G.

Vet tech waiting to meet your pet!
lexington, KY, 40515
13.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$35
per night

I left my two cats and dog with Bianca for several days while on vacation. I have never had someone take care of them or been away from them so long but she took incredible care of them, she was willing to accommodate for the three of them and was extremely good at communicating, answering any questions I had regarding their care and made me feel comfortable that my pets were in good hands! She truly cares for animals, never met anyone so dedicated! Would 100% recommend!

Sitter Profile Image: Toni T.
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Sitter Profile Image: Toni T.
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17.

Toni T.

Veterinary Technician Care
Lexington, KY, 40509
9.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$100
per night

Toni is an incredible human being who embodies the qualities of compassion, responsibility, and kindness. Toni has proven on multiple occasions her commitment to providing safe and loving care for my fur babies! Toni's dedication to ensuring the well-being of my pups is evident through her years of experience and the countless positive reviews from other pet owners. Her attention to detail and genuine love for animals shine through in every interaction. Toni goes above and beyond to meet the unique needs of each pet and ensure they feel comfortable and cherished. Not only is Toni an exceptional caregiver, but she also excels in customer service. Her professionalism and communication skills make pet owners feel at ease, knowing that their beloved companions are in capable hands. Toni's reliability and willingness to accommodate various schedules and special requests demonstrate her commitment to providing the best service possible. Toni's combination of expertise, empathy, and customer service skills makes her a standout choice for anyone seeking safe, loving care for their pets. She is truly an awesome human being who dedicates her time to making the lives of animals and their owners better.

Sitter Profile Image: Jeremy R.
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Sitter Profile Image: Jeremy R.
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18.

Jeremy R.

I'm here to pet sit and draw a dog.
Winchester, KY, 40391
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$63
per night

Jeremy has a big heart and is very responsible in all things, but especially when it comes to pets. He has patience with them, yet your pet still knows who is in charge. Jeremy has dog sat for me on a couple of different occasions and has taken good care of my dog. I've owned dogs for years yet Jeremy typically teaches me something new about them. I highly recommend Jeremy!

Sitter Profile Image: Kirsten B.
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Sitter Profile Image: Kirsten B.
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19.

Kirsten B.

I love working with all ages! 💕🐾
Winchester, KY, 40391
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$25
per night

Kirsten is an amazing caregiver for pets of all kinds! Considering her extensive history working in veterinary medicine and receiving numerous recognitions for her current job at BVS (Bluegrass Veterinary Specialties and Animal Emergency), she would be the perfect candidate for Rover. She would ease any concerns you may have about leaving your beloved pets behind in her dedicated hands.

Sitter Profile Image: Radhika M.
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Sitter Profile Image: Radhika M.
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20.

Radhika M.

Haaaanging Ouuuuut (with your pet)!
Winchester, KY, 40391
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$27
per night

I am very particular about my dog. I worry so much, & I didn’t worry at all this time. I highly recommend!!!

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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 3 reviews.

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