House Sitting in Winona

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Top rated Winona house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Cali R.
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Cali R.
Star Sitter
from
$60
per night
5 out of 5.0 stars
27 reviews
7 repeat clients
10 years of experience
Winona, MN, 55987

This is our 2nd time using Cali and we already have our 3rd time booked! She is professional, timely and we love her daily updates. Highly recommend!

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Jenni R.
Sitter Profile Image: Isabelle K.
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Isabelle K.
from
$35
per night
5 out of 5.0 stars
16 reviews
4 repeat clients
5 years of experience
Goodview, MN, 55987

Isabelle watched our three dogs while we were away for the weekend and did a great job! Our pups loved her, especially our pup that is usually very nervous around people he doesn't know. She was quick to respond to our initial request to have her pet sit and she sent lots of updates and pictures. We will definitely be asking her to watch our pups again for upcoming trips!

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Kristina K.
Sitter Profile Image: Jillissa R.
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Jillissa R.
Star Sitter
from
$27
per night
5 out of 4.9 stars
22 reviews
6 repeat clients
4 years of experience
Winona, MN, 55987

Jillissa stayed overnight with my fur babies. She kept in contact and sent pics with updates. I felt very comfortable with her in my home and will not hesitate to book with her again!

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Raylene H.
Sitter Profile Image: Ajia W.
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Ajia W.
Star Sitter
from
$65
per night
5 out of 5.0 stars
33 reviews
12 repeat clients
10 years of experience
Winona, MN, 55987

Ajia was great with Maverick! He was comfortable with her immediately and they had a great weekend while I was away. Definitely hope to have Ajia come hang with Mav again and would recommend her to anyone!

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Valerie C.
Sitter Profile Image: Rebekah L.
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Rebekah L.
from
$75
per night
5 out of 5.0 stars
24 reviews
10 repeat clients
6 years of experience
Winona, MN, 55987

Great sitter. Our dogs love Rebekah already after a single overnight stay. They were well cared for.

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Fred B.
Sitter Profile Image: Skylar M.
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Skylar M.
from
$60
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
4 years of experience
Winona, MN, 55987

Skylar is an absolute blessing ! She loves and attends to all of our babies like they are her own. We couldn't ask for a better fit for all of our animals.

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Debbie S.
Sitter Profile Image: Erica & Ciara M.
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Erica & Ciara M.
from
$75
per night
5 out of 4.9 stars
33 reviews
18 repeat clients
15 years of experience
Winona, MN, 55987

About: We’re Pawz & Play! We offer dog & cat boarding, weekend daycare, drop in visits, dog walking, and house sitting in Winona, MN. We operate on a small-scale, only taking a maximum of 2 pups or one family’s pets at a time. Erica is an aspiring dog groomer & trainer who someday hopes to have her own facility. Ciara is working on getting her bachelors and is the primary person on drop in visits. We have two medium sized young dogs who love to play & get along great with playful pups of all ages and sizes as well as an older small dog who does great with calmer pups. All dogs are assessed for play style and comfort level before being split into play groups. One of us is home the majority of the time and we incorporate your pets into our girls’ daily routine or we can do a rotation schedule if they’re not a fan of group activities. Our fenced in back yard has a good size dog run within the fence just for pups and the rest of the yard includes the chickens & rabbits in their own runs as well as a small patio, hammocks, and garden beds. Whether in your home or ours, we are happy to serve your pets whatever food you’d like including homemade, raw, canned food, or kibble. We just ask that it be premade so we need only measure out the amount and feed your babies.

Sitter Profile Image: Ashley D.
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Ashley D.
from
$40
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
8 years of experience
Buffalo City, WI, 54622

Ashley was great. Very thorough and took great care of Dove. She took excellent notes to make sure Dove had everything she needed to a T. I highly recommend Ashley and would book again in the future.

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Devin
Sitter Profile Image: Taylor D.
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Taylor D.
from
$30
per night
1 year of experience
Winona, MN, 55987

About: Although I am newer to dog sitting, I have stayed at family and friend’s homes with their dogs multiple times in the last year including following feeding schedules, walking, playing fetch, and more. I love to play fetch with dogs and sometimes end up enjoying it more than they do. I have a high energy personality that is also nurturing and sweet. I personally one day want at least one dog of my own so this is good experience in and of itself to learn about different breeds. I would love to get to know your dog :) I do work a job 8-5pm during the weekdays, but am open on the weekends and would be willing to stay the night at your home. I offer checking up on your dog during my open breaks during the day, playing fetch, walking your dog, pee breaks, and following a feeding schedule that you have. I am also open to learning new skills that you are open to teaching me and that are within your comfort.

Sitter Profile Image: Ellery A.
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Ellery A.
from
$27
per night
5 out of 5.0 stars
5 reviews
1 repeat client
15 years of experience
Winona, MN, 55987

About: I have taken care of a multitude of pets throughout my life, especially dogs of various sizes and breeds. Pets aren't just pets, they're family and I really truly resemble that through my care. I know how to care for your pets to keep them happy and healthy. I am a current college student with only a couple classes (maximum) a day, leaving me with lots of time to schedule for the rest of my day. I am easily able to frequently care for your furry friend as much as desired, and have lots of time to give them walks and belly rubs. I treat all animals that feel comfortable with lots of love and pets, and care for them like they're my own. I do not pull on the leash while walking, never punish with physical force, and treat all pets like family. I also respect everyone's homes and places of living, and will leave it just the same or better than when I came.

Sitter Profile Image: Alicia G.
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Alicia G.
from
$60
per night
5 out of 5.0 stars
97 reviews
14 repeat clients
33 years of experience
Winona, MN, 55987

About: I have had a love for animals my whole life! I used to be the neighborhood dog walker and brushing service growing up! I currently have two Golden Retrievers and a Cavapoo! I also breed my Golden Retriever so we get to raise Golden puppies until they go to their forever homes! I have plenty of references available! I am at home so I have a very wide open schedule to care for your pets! I am available for you Sunday through Saturday, morning, afternoon, and night! I will have your pets safely on leashes when outdoors in my care! We will take walks for exercise! Your fur babies are allowed to free roam in my home with my other 3 dogs! (I do have a crate if needed)

Sitter Profile Image: Abbey S.
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Abbey S.
from
$35
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
8 years of experience
Winona, MN, 55987

Abbey is very calm and capable. She took care of our two pups, and we were able to have a relaxing weekend away. We definitely hope to have her back again.

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Deborah H.
Sitter Profile Image: Austin K.
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Austin K.
from
$40
per night
7 years of experience
Winona, MN, 55987

About: I raised and since have consistently cared for my mom’s dog for the last 7.5 years. Additionally, friends and family have regularly asked for me to assist them with dog care. I have watched, walked, and spent the night with their pets. I have lots of energy and am capable of giving energetic dogs proper exercise through walks and/or play. I am also capable of relaxing and giving the proper care to pets that are more relaxed and need less exercise. I work from 7:30-4 every day, Monday through Friday, and am able to care for pets outside of this schedule, before or after the shift starts. I give lots of love and attention, but I do not force the dogs into uncomfortable situations. I allow them to communicate to me with their needs. I also have the capacity and am eager to play as much as the dog likes.

Sitter Profile Image: Olivia A.
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Olivia A.
from
$50
per night
5 out of 5.0 stars
2 reviews
10 years of experience
Winona, MN, 55987

Cooper looked so happy when we got home!

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Nancy K.
Sitter Profile Image: Jacque K.
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Jacque K.
from
$70
per night
5 out of 5.0 stars
10 reviews
2 repeat clients
18 years of experience
Winona, MN, 55987

Jacque was wonderful while staying with my puppy Atlas for the weekend! She provided me with great updates and pictures. I could tell Atlas really liked her and he was the same happy, sweet pup when I returned home!

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Courtney M.
Sitter Profile Image: Kalista Y.
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Kalista Y.
from
$27
per night
15 years of experience
Winona, MN, 55987

About: Hi there! My name is Kali, and I’ve been an animal lover my whole life. I grew up with dogs of all sizes and personalities, and they’ve always been a big part of my family. We also had a cat in the house, so I’m comfortable around both furry friends! Spending time with dogs is something I truly enjoy, whether it’s going for walks, playing in the yard, or just relaxing together. I’m patient, responsible, and always happy to match the energy level of your pup, whether they’re playful or more laid-back. I have experience with dogs of all ages, from puppies to senior dogs and I understand the different levels of care and attention each one needs. I’d love to meet your dog and make sure they feel safe, happy, and cared for while you’re away! Now through the end of August, I’m local in Winona and work remotely most days. I commute to La Crosse only on Wednesdays (7:30 AM – 3:30 PM), so I’m very available in Winona the rest of the week. Starting in September, I’ll be commuting to La Crosse Monday through Friday, and will be available for pet care after work hours. I’m also available some weekends, and I’ll always keep my availability updated here so you know exactly when I’m free. While I won’t be caring for pets in my own home, I take pride in providing attentive, respectful care in your pet’s home where they’re most comfortable and familiar with their surroundings. I’m happy to help with feeding, walks, playtime, crating, or anything else they need within reason. Your pet’s well-being is my top priority, and I’ll treat your home and animals with care and respect!

Sitter Profile Image: Elijah E.
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Elijah E.
from
$30
per night
15 years of experience
Winona, MN, 55987

About: I've trained service dogs and grew up with a lot of labs. I have always had a pet in my home from hamsters to horses on the ranch! Love animals from small to large. I am currently working part time with pets. I can work any day of the week including weekends! Would like to eventually make pet sitting a full time job! I have two large dogs at home that are loced in so many ways! Spoiled to the limit! The best boys I have been blessed with!

Sitter Profile Image: Madison B.
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Madison B.
from
$27
per night
8 years of experience
Winona, MN, 56587

About: I’ve taken care of dogs since I was young. I have raised some of my own as well. Neighbors would have me dog sit for weeks at a time. I am currently in between jobs so my availability is open! I am willing to accommodate schedules and work around things to ensure the best quality of care! My cat is treated like a princess. She goes on walks and never is bored. I stimulate her twice a day for a minimum of 2 hours. The world is only as big as you allow your pets to see.

Sitter Profile Image: Erin G.
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Erin G.
from
$38
per night
10 years of experience
Winona, MN, 55987

About: I have worked at a dog boarding facility for over two years providing high quality care for all different kinds of pups and their needs! I also have an old pup myself who is spoiled with belly rubs and treats who is currently at home with my parents while I attend college! I can accommodate to any needs you and your dog need like a specialized feeding schedule, allergies, exercise, and more! Pet care has fit into my schedule daily from working at a pet boarding facility to taking care of my own pup! I am constantly giving service to any pups that need it to keep them and myself busy! Your pets will be cared for with high quality service and love! I treat every dog like it is my own and spoil them with that they love doing! If your dog is a cuddler then I can provide cuddles and if your dog likes walking I can walk all day long!

Sitter Profile Image: Michelle N.
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Michelle N.
from
$25
per night
5 out of 5.0 stars
3 reviews
45 years of experience
Winona, MN, 55987

Michelle took great care of our two dogs and one cat while we were away. Our dogs felt comfortable around her right away. Michelle was flexible and communicative.

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Florian B.
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Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

Sitter Profile Image: Cali R.
Verified Enhanced Background Check
Sitter Profile Image: Cali R.
Verified Enhanced Background Check

Cali R.
Star Sitter

I was a veterinary assistant!
Winona, MN, 55987
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
27 reviews
7 repeat clients
Profile image

This is our 2nd time using Cali and we already have our 3rd time booked! She is professional, timely and we love her daily updates. Highly recommend!

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Isabelle K.
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Sitter Profile Image: Isabelle K.
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Isabelle K.

I LOVE all dogs, at any age or size
Goodview, MN, 55987
3.7 mi. away
House Sitting, Drop-In Visits
from
$35
per night
5 out of 5.0 stars
16 reviews
4 repeat clients
Profile image

Isabelle watched our three dogs while we were away for the weekend and did a great job! Our pups loved her, especially our pup that is usually very nervous around people he doesn't know. She was quick to respond to our initial request to have her pet sit and she sent lots of updates and pictures. We will definitely be asking her to watch our pups again for upcoming trips!

Availability updated 74 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jillissa R.
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Sitter Profile Image: Jillissa R.
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Jillissa R.
Star Sitter

🦮/🐈‍⬛-sitting, check-ins, walks
Winona, MN, 55987
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$27
per night
5 out of 4.9 stars
22 reviews
6 repeat clients
Profile image

Jillissa stayed overnight with my fur babies. She kept in contact and sent pics with updates. I felt very comfortable with her in my home and will not hesitate to book with her again!

Availability updated yesterday
Sitter Profile Image: Ajia W.
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Sitter Profile Image: Ajia W.
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Ajia W.
Star Sitter

Full Time Pro. Pet+Home Care 😁
Winona, MN, 55987
13.0 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$65
per night
5 out of 5.0 stars
33 reviews
12 repeat clients
Profile image

Ajia was great with Maverick! He was comfortable with her immediately and they had a great weekend while I was away. Definitely hope to have Ajia come hang with Mav again and would recommend her to anyone!

Availability updated 5 days ago
Sitter Profile Image: Rebekah L.
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Sitter Profile Image: Rebekah L.
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Rebekah L.

Loving care to EvErY pup and kitty!
Winona, MN, 55987
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
24 reviews
10 repeat clients
Profile image

Great sitter. Our dogs love Rebekah already after a single overnight stay. They were well cared for.

Availability updated 23 days ago
Sitter Profile Image: Skylar M.
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Sitter Profile Image: Skylar M.
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Skylar M.

I work at Winona Humane Society!
Winona, MN, 55987
0.3 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
Profile image

Skylar is an absolute blessing ! She loves and attends to all of our babies like they are her own. We couldn't ask for a better fit for all of our animals.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Erica & Ciara M.
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Sitter Profile Image: Erica & Ciara M.
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Erica & Ciara M.

Pawz & Play— Your Pets are Family
Winona, MN, 55987
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 4.9 stars
33 reviews
18 repeat clients

Ciara did drop in visits for me when I first got my new puppy. She was great with her and the puppy had so many fewer accidents than she would have if I’d only come home on lunch! She also did a great job with the puppy on positive crate association. Now the puppy knows kennel means she goes in the crate and she has no complaints.

Availability updated 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Ashley D.
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Sitter Profile Image: Ashley D.
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Ashley D.

Leave your pets in good hands!
Buffalo City, WI, 54622
17.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
Profile image

Ashley was great. Very thorough and took great care of Dove. She took excellent notes to make sure Dove had everything she needed to a T. I highly recommend Ashley and would book again in the future.

Availability updated 40 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Taylor D.
Verified Enhanced Background Check
Sitter Profile Image: Taylor D.
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Taylor D.

Just a girl who loves to play fetch
Winona, MN, 55987
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
1 year of experience

About: Although I am newer to dog sitting, I have stayed at family and friend’s homes with their dogs multiple times in the last year including following feeding schedules, walking, playing fetch, and more. I love to play fetch with dogs and sometimes end up enjoying it more than they do. I have a high energy personality that is also nurturing and sweet. I personally one day want at least one dog of my own so this is good experience in and of itself to learn about different breeds. I would love to get to know your dog :) I do work a job 8-5pm during the weekdays, but am open on the weekends and would be willing to stay the night at your home. I offer checking up on your dog during my open breaks during the day, playing fetch, walking your dog, pee breaks, and following a feeding schedule that you have. I am also open to learning new skills that you are open to teaching me and that are within your comfort.

Availability updated 19 days ago
Sitter Profile Image: Ellery A.
Verified Enhanced Background Check
Sitter Profile Image: Ellery A.
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Ellery A.

Life-Long Dog Lover
Winona, MN, 55987
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$27
per night
5 out of 5.0 stars
5 reviews
1 repeat client

Ellery is a good friend of mine, she is very responsive and trustworthy. She is a very timely person and good at getting any tasks done on time and done well. She has many pets and cares for them all well. She has a very compassionate personality and would be a good dog walker/sitter.

Availability updated 33 days ago
Sitter Profile Image: Alicia G.
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Sitter Profile Image: Alicia G.
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Alicia G.

Golden Guardian
Winona, MN, 55987
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
97 reviews
14 repeat clients

About: I have had a love for animals my whole life! I used to be the neighborhood dog walker and brushing service growing up! I currently have two Golden Retrievers and a Cavapoo! I also breed my Golden Retriever so we get to raise Golden puppies until they go to their forever homes! I have plenty of references available! I am at home so I have a very wide open schedule to care for your pets! I am available for you Sunday through Saturday, morning, afternoon, and night! I will have your pets safely on leashes when outdoors in my care! We will take walks for exercise! Your fur babies are allowed to free roam in my home with my other 3 dogs! (I do have a crate if needed)

Availability updated 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Abbey S.
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Sitter Profile Image: Abbey S.
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Abbey S.

College Student Missing Dogs
Winona, MN, 55987
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 5.0 stars
10 reviews
4 repeat clients
Profile image

Abbey is very calm and capable. She took care of our two pups, and we were able to have a relaxing weekend away. We definitely hope to have her back again.

Availability updated today
Sitter Profile Image: Austin K.
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Sitter Profile Image: Austin K.
Verified Enhanced Background Check

Austin K.

Lots of energy to exercise your dog
Winona, MN, 55987
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
2 reviews

Austin is a very responsible and caring young man. He takes care of his animals well and makes sure they're as happy and healthy as can be. His commitment to care is unwavering.

Availability updated yesterday
Sitter Profile Image: Olivia A.
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Sitter Profile Image: Olivia A.
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Olivia A.

Your pets new best friend!
Winona, MN, 55987
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
2 reviews
Profile image

Cooper looked so happy when we got home!

Availability updated 18 days ago
Sitter Profile Image: Jacque K.
Verified Background Check
Sitter Profile Image: Jacque K.
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Jacque K.

Jacq’s Doggy Day Care and Services
Winona, MN, 55987
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$70
per night
5 out of 5.0 stars
10 reviews
2 repeat clients
Profile image

Jacque was wonderful while staying with my puppy Atlas for the weekend! She provided me with great updates and pictures. I could tell Atlas really liked her and he was the same happy, sweet pup when I returned home!

Availability updated 82 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kalista Y.
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Sitter Profile Image: Kalista Y.
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Kalista Y.

Lifelong Dog Lover with Experience!
Winona, MN, 55987
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$27
per night
1 review

I highly recommend Kali as a pet sitter, she loves all animals especially dogs! She has been nothing but amazing with my dog since he was a puppy until 3 years old now. She truly loves him like her own and would treat all pets this way. I know my dog is in great hands when Kali watches him, she is a very reliable and loving caregiver.

Availability updated 11 days ago
Sitter Profile Image: Elijah E.
Verified Enhanced Background Check
Sitter Profile Image: Elijah E.
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Elijah E.

Animal lover from small animals to
Winona, MN, 55987
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
15 years of experience

About: I've trained service dogs and grew up with a lot of labs. I have always had a pet in my home from hamsters to horses on the ranch! Love animals from small to large. I am currently working part time with pets. I can work any day of the week including weekends! Would like to eventually make pet sitting a full time job! I have two large dogs at home that are loced in so many ways! Spoiled to the limit! The best boys I have been blessed with!

Availability updated 39 days ago
Sitter Profile Image: Madison B.
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Sitter Profile Image: Madison B.
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Madison B.

Dogs are the best companions!
Winona, MN, 56587
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$27
per night
8 years of experience

Madison (Maddy) is a responsible person who will have nothing but the pets best interest and safety in mind when caring for them. She loves animals and grew up caring for them. She will do a great job.

Availability updated today
Sitter Profile Image: Erin G.
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Sitter Profile Image: Erin G.
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Erin G.

Professional belly-rubber & cuddler
Winona, MN, 55987
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$38
per night
1 review

Erin has a heart of gold. She has gone above and beyond in caring for our precious family pets. She lovingly cared for Lucky, our cat who is still happy and healthy, and Rusch, our beloved dog who has since passed, while my husband was hospitalized. Although we missed them dearly, we knew they were in the best hands. Erin treats every pet as if they were her own, showering them with love, ensuring they are well-fed, and attentively meeting their every need. Her compassion, reliability, and dedication would make her a wonderful addition to your team!

Availability updated yesterday
Sitter Profile Image: Michelle N.
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Sitter Profile Image: Michelle N.
Verified Background Check

Michelle N.

Home full-time. Large yard.
Winona, MN, 55987
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per night
5 out of 5.0 stars
3 reviews
Profile image

Michelle took great care of our two dogs and one cat while we were away. Our dogs felt comfortable around her right away. Michelle was flexible and communicative.

Availability updated 7 months ago

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