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)?

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Sitter Profile Image: Pam W.
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Sitter Profile Image: Pam W.
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1. 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
4 reviews
1 repeat client
from
$50
per night

Pam was great. She made sure the dogs were fed and let out multiple times. She provided a lot of great updates and left great notes about their activities.

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Sitter Profile Image: Travis M.
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Sitter Profile Image: Travis M.
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2. 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
3 repeat clients
from
$65
per night

Travis did a great job with our two dogs and cat! He was very attentive and caring to our animals, which we greatly appreciated. He sent us pictures and kept in touch with us daily too, which we asked for and loved. He was also very responsible at our home and left it in the same condition in which he found it. Highly recommend and will hire him again.

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Sitter Profile Image: Nicole Z.
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Sitter Profile Image: Nicole Z.
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3. 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

Nikki sent me a couple of sweet pics each day of our little guy while we were gone. Seems like he got some good cuddles and treats. As far as I can tell he was well cared for. The only thing I wish we’d communicated better about is how much time was spent with our cuddle bear. Just been curious is all but I’m confident it was sufficient and most likely more than enough. She always responded in a timely manner to any messages. I would use her again in the future ?

Sitter Profile Image: Erin M.
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Sitter Profile Image: Erin M.
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4. Erin M.

I love dogs!
Madison, WI, 53704
8.8 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
3 reviews
1 repeat client
from
$50
per night

Erin did a great job watching my 14 year old Shiba Inu! She took him on several walks which he loved and kept me updated on well he was doing. I am definitely a repeat customer!

Sitter Profile Image: Avery C.
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Sitter Profile Image: Avery C.
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5. Avery C.

Rover 101
Animal Whisperer Filling The Void
Madison, WI, 53703
9.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
45 reviews
12 repeat clients
from
$100
per night

Avery did a fantastic job watching our Charlie for two nights! She was responsible, great with Charlie, and super communicative, sending us photos and videos along the way. She clearly loves and understands dogs, and we'd gladly have her back sometime in the future.

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Sitter Profile Image: Tommy M.
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Sitter Profile Image: Tommy M.
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6. Tommy M.

I will treat your pet as my own!
Madison, WI, 53703
9.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$55
per night

Tommy took care of my dog with lots of care and respect, and we would definitely recommend him to other pet parents looking for sitting services in his area! :)

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Sitter Profile Image: Lisa R.
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Sitter Profile Image: Lisa R.
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7. Lisa R.

Pet care like they are my own!
Waunakee, WI, 53597
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$70
per night

Lisa is AWESOME….FANTASTIC….CARING. There isn’t a word that I can think of to express my gratitude for taking such WONDERFUL care of our 2 dogs. She took them on multiple walks a day and played in backyard with them . She also updated us daily with pics and videos so we had nothing to worry about. Highly recommend!

Confirmed availability: Easter Weekend
Sitter Profile Image: Laurie M.
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Sitter Profile Image: Laurie M.
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8. 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

I could not have been more pleased with the way Laurie cared for my three senior dogs while I was overseas for 10 days. I have never been that faraway from them for an extended period of time but she managed everything so well I was able to relax and enjoy my trip. I highly recommend her compassionate pet care and attention to house details.

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Sitter Profile Image: Jolene V.
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Sitter Profile Image: Jolene V.
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9. Jolene V.

Passionate about pets
McClellan Park, Madison, WI, 53718
9.0 mi. away
Boarding, House Sitting
5.0 out of 5 stars
27 reviews
6 repeat clients
from
$60
per night

Jolene did a wonderful job caring for our pets while we were on a week-long vacation! She was so patient and kind with our rescue dog, Dino. Even though he doesn't snuggle much with strangers, Jolene at least got some cuddles from our cat, Camila! Our house was also in perfect shape when we returned. We will definitely be booking with Jolene again!

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Sitter Profile Image: Jenna H.
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Sitter Profile Image: Jenna H.
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10. 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: Leticia S.
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Sitter Profile Image: Leticia S.
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11. 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

Was super flexible with watching our sick puppy during the day. Very trustworthy and worked to gain the trust of our sometimes anxious dog. Would highly suggest using her services!!

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Sitter Profile Image: Tina B.
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Sitter Profile Image: Tina B.
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12. 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
53 reviews
20 repeat clients
from
$35
per night

She did a great job watching our boys and everyone was well taken care of. She was even able to bring in some of our mail which was really appreciated!

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Sitter Profile Image: Ella M.
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Sitter Profile Image: Ella M.
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13. Ella M.

Dying to befriend your pet!
Hawthorne, Madison, WI, 53714
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night

Ella has a big heart for animals and meticulous attention to detail. We have traded off pet responsibilities for years, and she still surprises me with the amount of time and energy she devotes to an animal for a simple weekend away. She is good at responding and adjusting to an animals needs, isn't afraid to ask for clarification, and treats every creature with the same level of obsessive love that she treats her own. I recommend her as a fantastic caregiver for your pets!

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Sitter Profile Image: Carla P.
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Sitter Profile Image: Carla P.
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14. Carla P.

Dog-loving family ready to help!
Sun Prairie, WI, 53590
4.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
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: Natalie W.
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Sitter Profile Image: Natalie W.
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15. 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!

Confirmed availability: Easter Weekend
Sitter Profile Image: Tonisha A.
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Sitter Profile Image: Tonisha A.
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16. 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: Mariana P.
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Sitter Profile Image: Mariana P.
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17. Mariana P.

I am an animal lover!!!!
sun prairie, WI, 53590
4.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
53 reviews
17 repeat clients
from
$90
per night

Mariana went above and beyond. Taking such good care of my dogs and even cleaning before I got back. She is wonderful and I will certainly be using her again.

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Sitter Profile Image: Alicia D.
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Sitter Profile Image: Alicia D.
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18. Alicia D.

Dog lover happy to care for pups!
Madison, WI, 53714
8.1 mi. away
Boarding, House Sitting, Dog Walking
5.0 out of 5 stars
29 reviews
8 repeat clients
from
$38
per night

Alicia stayed at our home with our 2 golden retrievers for a week and she did a fantastic job. We came home to two happy dogs and a clean tidy home. She sent lots of photos and communicated with us regularly. We would definitely recommend her to others and we hope she’ll stay with our boys again in the future when we leave town.

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Sitter Profile Image: Emily B.
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Sitter Profile Image: Emily B.
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19. Emily B.

Experience with multiple species!
Sun Prairie, WI, 53590
6.7 mi. away
House Sitting
5.0 out of 5 stars
15 reviews
4 repeat clients
from
$65
per night

Our first contract with Emily. She was great with communication and with caring for our two doxies. She sent us pictures and updates everyday. I would feel very comfortable with having Emily return in the future, and highly recommend her.

Confirmed availability: Easter Weekend
Sitter Profile Image: Eastyn L.
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Sitter Profile Image: Eastyn L.
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20. Eastyn L.

no pet to big or small!
DeForest, WI, 53532
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$28
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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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.

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