House Sitting in Windsor

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
Which dates do you need?
What size are your dogs (lbs)?

Search Results

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Sitter Profile Image: Travis M.
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Sitter Profile Image: Travis M.
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1. Travis M.

Reliable, caring dog-lover
MONONA, WI, 53713
11.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
4 repeat clients
from
$55
per night
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We had Travis stay with our dog again, and it was seamless. He is so conscientious and considerate. Our dog loves him and again the house looks great! I highly recommend him!

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Sitter Profile Image: Aurora R.
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Sitter Profile Image: Aurora R.
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2. Aurora R.

Your Dog's Best Friend
Madison, WI, 53705
11.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$45
per night
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Aurora was great and took such great care of our Ollie!

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Sitter Profile Image: Tina B.
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Sitter Profile Image: Tina B.
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3. Tina B.

Animal lover doing what I enjoy
Windsor, WI, 53598
0.1 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
55 reviews
20 repeat clients
from
$35
per night
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Tina went above and beyond to come take care of our pets. I trust that she does a great job and my pups love the company of her and her kiddos. Would recommend and will use again 😊

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Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
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4. Sarah W.

Pet lover with vet assistant exp.
Madison, WI, 53704
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$35
per night

I have known Sarah for over 20 years. Throughout our friendship, Sarah has always been a compassionate advocate for pets. She worked at the local vet clinic for a few years after high school. She often stops in to take care of our pets when we are out of town. I know she checks in on our other friends’ pets as well. She is very trustworthy and has a huge heart for animals. Working for Rover sounds like a perfect fit for Sarah!

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Sitter Profile Image: Ella W.
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Sitter Profile Image: Ella W.
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5. Ella W.

Hi, my name is Ella!!
Ridgewood, Madison, WI, 53704
7.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$40
per night
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Ella watched my dogs overnight and did a phenomenal job. She gave lots of great updates and followed our instructions. I will definitely be booking her again and would highly recommend

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Sitter Profile Image: Jessica M.
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Sitter Profile Image: Jessica M.
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6. Jessica M.

Passion for all animals
Reston Heights, Madison, WI, 53718
10.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$50
per night
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Jessica saved the day and helped me out last minute with my doggo. She was communicative and professional. My dog seemed to have a great time and really enjoyed her company! Thanks Jessica!

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Sitter Profile Image: Pam W.
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Sitter Profile Image: Pam W.
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7. Pam W.

Dogs LOVE me / I LOVE dogs
Sun Prairie, WI, 53590
5.6 mi. away
Boarding, House Sitting
5.0 out of 5 stars
14 reviews
5 repeat clients
from
$75
per night
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Pam was amazing a great communicator Ruby really warmed up to her quickly you can tell she is a trusting and responsible human. Thank you for taking such great care of Ruby while I was on my work trip

Sitter Profile Image: Leah M.
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Sitter Profile Image: Leah M.
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8. Leah M.

Rover 101
Calling all pet parents!
Waunakee, WI, 53597
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
13 repeat clients
from
$75
per night
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We are thrilled with Leah and her mix of professionalism and kindness. She stayed with Myles for the weekend and really put us at ease with leaving him for the first time. She even helped with some training. Such a pro!

Sitter Profile Image: Alicia D.
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Sitter Profile Image: Alicia D.
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9. Alicia D.

Dog lover happy to care for pups!
Madison, WI, 53714
8.1 mi. away
Boarding, House Sitting
5.0 out of 5 stars
49 reviews
14 repeat clients
from
$50
per night
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Alicia is fantastic! Our 2 Chihuahuas can be alot but they do really well with Alicia! We are so thankful!! We don’t worry at all about the doggies when we travel 😊

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Sitter Profile Image: Katie G.
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Sitter Profile Image: Katie G.
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10. Katie G.

My Yorki is my best friend
waunakee, WI, 53597
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$25
per night
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Katie was amazing! Sent plenty of photo updates. Our dog was a bit scared at first but Katie made sure to let us know when she warmed up to her. We ended up having to cut our trip short and Katie was quick to respond with no issues.

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Sitter Profile Image: Megan W.
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Sitter Profile Image: Megan W.
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11. Megan W.

Your Best Friend’s New Best Friend!
Sun Prairie, WI, 53590
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
116 reviews
36 repeat clients
from
$125
per night
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We has a great experience with Megan who watched our senior after surgery. She’s awesome and has great experience with dogs. I felt so comfortable leaving for our one night stay. If you want peace of mind hire Megan!

Sitter Profile Image: Megan B.
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Sitter Profile Image: Megan B.
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12. Megan B.

Vet tech & pet photographer
Windsor, WI, 53598
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
49 reviews
23 repeat clients
from
$55
per night
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We are so happy to have met Megan. She is very attentive and caring. I recommend her highly and we will definitely have her back again. Thank you Megan!!

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Sitter Profile Image: Maya F.
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Sitter Profile Image: Maya F.
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13. Maya F.

Vet Tech & Cat Mom!
Sun prairie, WI, 53590
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
34 repeat clients
from
$115
per night
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Maya did a fantastic job taking care of my kitty Princess, who has some special needs and requires daily medications. She was super responsive and sent me daily updates and pictures so I did not worry. Thanks again for taking such good care of my sweet girl!

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Sitter Profile Image: Tonisha A.
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Sitter Profile Image: Tonisha A.
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14. Tonisha A.

Your dog will be like family!
Sun Prairie, WI, 53590
5.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
9 repeat clients
from
$60
per night
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Tonisha has taken care of our pups before for drop in visits and walks. This service was for overnight and as usual, she did an outstanding job! My pups love her so we know they are always well cared for:)

Sitter Profile Image: Leticia S.
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Sitter Profile Image: Leticia S.
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15. Leticia S.

Great energy and we are cool cats!
Sun Prairie, WI, 53590
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
1 repeat client
from
$60
per night
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Leticia was wonderful as a cat sitter for us. Responsive, reliable, friendly, and very loving to the cats while I was away. I highly recommend her!

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Sitter Profile Image: Kena L.
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Sitter Profile Image: Kena L.
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16. Kena L.

Your dogs new best friend
Sun Prairie, WI, 53590
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
3 repeat clients
from
$65
per night

About: I’ve been an animal lover my entire life and am commonly dubbed “the animal whisperer” amongst friends and family. I grew up with a zoo of animals- dogs, a cat, a lizard, guinea pigs, birds, many, MANY fish, and even a spider! I worked at a doggie daycare for 1.5 years and an animal shelter (that had dogs, cats, and even rats!) for 1.5 years as well. In that time I’ve developed skills in feeding, walking, caring for, playing with, first aid, grooming, and even measuring and administering medication to furry friends of all shapes and sizes. In my time working with animals I’ve met some of the friendliest fur balls, ones with special needs (blind, deaf, missing legs, you name it), and even the more grumpy guys. I’m currently a college student as well as an athlete. My schedule tends to vary from week to week but always have the time to work in some much needed dog and cat time before, between, and after classes (and free weekends!) I live by the saying where you should leave places nicer than they were when you arrived. If your fur babies have any accidents they will be picked up ASAP! I only touch what I am told to and only go in rooms I am instructed to go into.

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Sitter Profile Image: Eastyn L.
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Sitter Profile Image: Eastyn L.
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17. Eastyn L.

no pet to big or small!
DeForest, WI, 53532
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
5 repeat clients
from
$50
per night

Eastyn takes care of cats, goats, chickens, and dogs, and every time I see her with an animal, she treats it with love and respect. She is a very gentle and loving person and is a great companion for any animal. She’s very attentive and affectionate with all the animals she takes care of, even if they are misbehaving. Would 100% recommend!

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Sitter Profile Image: Carla P.
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Sitter Profile Image: Carla P.
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18. Carla P.

Dog-loving family ready to help!
Sun Prairie, WI, 53590
4.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$28
per night

Carla is outstanding!! She is very kind, loving, and cares a great deal about the animals in her life. Carla is also very punctual, accommodating, and responsible. I would trust her in a heartbeat with my beloved animals.

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Sitter Profile Image: Jasmine W.
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Sitter Profile Image: Jasmine W.
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19. Jasmine W.

Dogs get all the Zoomies!!
Deforest, WI, 53532
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$48
per night
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Very good dog and cat sitter! Great communication with me.

Sitter Profile Image: Kirstyn M.
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Sitter Profile Image: Kirstyn M.
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20. Kirstyn M.

I’ve Got Your Tail Covered
Deforest, WI, 53532
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
7 repeat clients
from
$40
per night

About: I’ve taken care of puppies to senior dogs since I was a little girl. My dad owned a doggy daycare and it was a great experience learning how to care for animals. I currently work full time and I go to school. Pet care will fit into my schedule because I do work night shift. I will have plenty of time to properly care for your pets. I will be there to watch your home and make sure your pet is safe. I will follow all of your instructions to assure that I keep everyone safe.

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Rover also offers House Sitting in:

Rover also offers other services in Windsor:


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Windsor house sitting needs. On Rover, it's easy to find a loving dog sitter in Windsor who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Windsor house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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 dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Windsor for your dog — people who'll treat him like family.

House Sitting