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
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What size are your dogs (lbs)?

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Sitter Profile Image: Devon G.
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Sitter Profile Image: Devon G.
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1. Devon G.

Keep pets safe and happy
Fitchburg, WI, 53711
15.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
5 repeat clients
from
$28
per night

Devon took great care of our two pups! With me having s short notice request, I was so relieved Devon was able to schedule a meet and greet with us Sunday and dog sit in our home Monday - Tuesday. We’ll definitely book Devon for future dog sitting needs!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Nathan K.
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Sitter Profile Image: Nathan K.
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2. Nathan K.

Compassion, Experience, & Integrity
Deforest, WI, 53532
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$45
per night

Nathan is very conscientious and great with pets. Would highly recommend!

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Sitter Profile Image: Jess F.
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Sitter Profile Image: Jess F.
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3. Jess F.

Friendly neighborhood extrovert!
Madison, WI, 53718
13.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$34
per night

Jess has been wonderful to work with! Our Elle loves her so much and is so comfortable with her vs going to a dog boarder while I’m out of town. So thankful for such wonderful help!

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Sitter Profile Image: Pam W.
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Sitter Profile Image: Pam W.
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4. Pam W.

Dogs LOVE me / I LOVE dogs
Sun Prairie, WI, 53590
5.6 mi. away
Boarding, House Sitting, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$50
per night

Pam was wonderful with our two dogs! Even with our second dog, who can be quite reactive with new folks, she settled in and made both dogs feel very comfortable. She stayed a weekend in our home while we traveled and really helped us feel like our dog and home were in great hands.

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Sitter Profile Image: Travis M.
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Sitter Profile Image: Travis M.
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5. Travis M.

Reliable, caring dog-lover
Madison, WI, 53718
9.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
4 repeat clients
from
$65
per night

Travis is truly remarkable! We arranged a meet and greet where he invested time in getting to know our dog. He made sure to understand Remy's needs and ensured a perfect match. Travis went above and beyond by agreeing to house and Dog sit for 8 days. During his stay, Remy not only had the pleasure of regular walks but also relished the companionship at home. It's evident that Travis provided a level of care that exceeded our expectations. Our home was left in pristine condition, and to top it off, our neighbors were quick to compliment Travis on his friendly demeanor. Remy, our Husky German Shepherd Rescue, is eagerly anticipating his next stay with Travis. It's heartening to see such a positive connection between them. Travis has proven to be more than just a sitter; he's become a trusted companion for Remy. We're grateful to have found such a reliable and caring individual for our beloved pet.

Sitter Profile Image: Tina B.
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Sitter Profile Image: Tina B.
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6. 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

Tina is so pleasant and accommodating. She was extremely patient with our fearful dog and kept us updated the entire time away. She was excellent at providing recommendations to help us figure out better ways to make our time away easier on our puppy.

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Sitter Profile Image: Alicia D.
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Sitter Profile Image: Alicia D.
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7. Alicia D.

Dog lover happy to care for pups!
Worthington Park, Madison, WI, 53714
8.1 mi. away
Boarding, House Sitting
5.0 out of 5 stars
34 reviews
8 repeat clients
from
$50
per night

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: Kaylee C.
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Sitter Profile Image: Kaylee C.
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8. Kaylee C.

Doggos&Cattos r better than people
University Apartments, Madison, WI, 53705
10.4 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$50
per night

Kaylee was fantastic! She was communicative, punctual, and went above and beyond expectations. I felt very comfortable leave my anxious dog in her care. I got many updates from her, with pictures! She was respectful and left the house in great shape. I highly recommend her.

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Sitter Profile Image: Leah M.
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Sitter Profile Image: Leah M.
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9. 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
23 reviews
15 repeat clients
from
$80
per night

Amazing. We used Leah in the past for a few walks but this time she was with Teddy for a full long weekend. We cannot express how happy we are with everything. Teddy was in great spirits when we arrived home. Leah also give us full reports while we were away, it was as if we were there. Booking Leah again for next week.

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Sitter Profile Image: Nicole Z.
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Sitter Profile Image: Nicole Z.
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10. Nicole Z.

Lover of ALL pets!
Waunakee, WI, 53597
6.5 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$40
per night

Nicole was fantastic!!! Our first time using Rover and she made the process very smooth. Our dog Jack was in heaven the whole weekend. She sent updates each day and let us know how he was doing. We will for sure be using Nicole again! ?

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Sitter Profile Image: Natalie W.
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Sitter Profile Image: Natalie W.
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11. Natalie W.

Graduate student & dog lover
Madison, WI, 53704
7.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
4 repeat clients
from
$49
per night

Natalie was excellent with my pup when I was away for a weekend! Great house guest and my dog had a great time. Excellent communicator! Will absolutely be hiring her again!

Sitter Profile Image: Leticia S.
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Sitter Profile Image: Leticia S.
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12. 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

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: Tonisha A.
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Sitter Profile Image: Tonisha A.
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13. 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
34 reviews
9 repeat clients
from
$60
per night

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:)

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Sitter Profile Image: Fayth C.
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Sitter Profile Image: Fayth C.
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14. Fayth C.

Pets are the most important
Madison, WI, 53704
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$30
per night

I had a chow/ golden retriever mix. Fayth was the only person I trusted to care for him when I was away. His last years, he needed medication and had several other special needs as well. She was compassionate and patient with him.

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Sitter Profile Image: Jenna H.
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Sitter Profile Image: Jenna H.
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15. Jenna H.

Pet parent+caretaker🐶🥰🐈
Sun Prairie, WI, 53590
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
6 repeat clients
from
$90
per night

Jenna went above and beyond for me and for Gus! She sent many pictures, kept me updated, and couldn’t have done anything better! 10/10 recommend

Sitter Profile Image: Kirstyn M.
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Sitter Profile Image: Kirstyn M.
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16. 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
16 reviews
6 repeat clients
from
$30
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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Sitter Profile Image: Laurie M.
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Sitter Profile Image: Laurie M.
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17. Laurie M.

Licensed Vet Tech🩺 🐶❤️😻
DeForest, WI, 53532
2.1 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
16 reviews
from
$100
per night

Laurie was fantastic at providing updates, asking lots of detailed questions, and minimizing disruption for our pets during an overnight visit. We were uneasy about leaving our dog the weekend, as he was recently diagnosed with some medical needs, but Laurie handled everything like a pro. We hope to work with her again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Rose G.
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Sitter Profile Image: Rose G.
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18. Rose G.

Future vet tech for a helping hand
DeForest, WI, 53532
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$40
per night

Rose was super accommodating, incredibly polite and diligent, and took such amazing care of our cat and dog. We'll definitely have her back!

Sitter Profile Image: Autumn M.
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Sitter Profile Image: Autumn M.
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19. Autumn M.

God~Family~Teaching
Deforest, WI, 53532
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$35
per night

Very pleased with Autumn, we will definitely be using her again.

Sitter Profile Image: Jasmine W.
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Sitter Profile Image: Jasmine W.
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20. Jasmine W.

Dogs get all the Zoomies!!
Deforest, WI, 53532
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$48
per night

Very good dog and cat sitter! Great communication with me.

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Windsor House Sitting ratings

Overall Rating:
4.8 out of 5 stars

House sitters in Windsor are rated on average 4.8 out of 5 stars based on 26 reviews.

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