House Sitting in Windsor

Find a loving house sitter to watch over your pets and your home.

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Top rated Windsor house sitters

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

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Sitter Profile Image: Emma R.
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Emma R.
from
$30
per night
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Sun Prairie, WI, 53590

Emma was great with our puppy and dog!

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Cassie J.
Sitter Profile Image: Cassandra B.
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Cassandra B.
Star Sitter
from
$35
per night
5.0 out of 5 stars
38 reviews
11 repeat clients
15 years of experience
Madison, WI, 53704

Cassie was wonderful! We had no worries, as we were gone for 11 days. She stayed at our home, so it didn’t stress out our dog, Zoe. Cassie was very proactive with asking detailed questions about her and just genuinely concerned about all her needs. She even suggested coming over for some visits prior to our vacation, so Zoe could get use to her. Highly recommend!!?

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Tammy B.
Sitter Profile Image: Tina B.
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Tina B.
Star Sitter
from
$35
per night
4.9 out of 5 stars
76 reviews
22 repeat clients
38 years of experience
Windsor, WI, 53598

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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Steven W.
Sitter Profile Image: Renee L.
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Renee L.
from
$40
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Sun Prairie, WI, 53590

Renee was wonderful with our 2 puppies. One even had an accident and she called us to find out what she should do. We have a shampooer. She asked how to use it and actually shampooed their floor for us. She treated our puppies so good. Playing outside and walking. I would hire her again.

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Mark M.
Sitter Profile Image: Sylvia L.
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Sylvia L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
9 years of experience
Ridgewood, Madison, WI, 53704

Sylvia did an amazing job! Everything went smoothly and she was flexible with care given the extremely cold weather. We highly recommend and will definitely be a repeat customer.

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Jill M.
Sitter Profile Image: Tiana B.
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Tiana B.
from
$50
per night
5.0 out of 5 stars
30 reviews
12 repeat clients
5 years of experience
DeForest, WI, 53532

Tiana was amazing with our dog and the house was well cared for while gone for an extended period of time. She provided regular updates with pictures that were much appreciated when we started to miss our baby girl.

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Sylvia L.
Sitter Profile Image: Della H.
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Della H.
from
$40
per night
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Windsor, WI, 53598

Della was wonderful with our dog Lacy.

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Steve M.
Sitter Profile Image: Krista I.
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Krista I.
from
$53
per night
5.0 out of 5 stars
7 reviews
5 years of experience
Sun Prairie, WI, 53590

Krista was great! She asked thorough questions and sent pictures throughout the day - no complaints!

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Erin D.
Sitter Profile Image: Brenda S.
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Brenda S.
from
$40
per night
4.9 out of 5 stars
31 reviews
11 repeat clients
9 years of experience
Waunakee, WI, 53597

Brenda was amazing!!! She took great care of our house and our cats. Sent pictures and updates, and left the house cleaner than she found it. 😁 We needed last minute help, and she was so flexible and accommodating! I would not hesitate to hire her again!

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Alicia S.
Sitter Profile Image: Karina M.
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Karina M.
from
$45
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Karina was wonderful. She took care of our dog overnight and stayed at our house. Everything went very well, and Archie loved her. I will definitely use her again.

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Laurie P.
Sitter Profile Image: Shatoria W.
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Shatoria W.
Star Sitter
from
$68
per night
5.0 out of 5 stars
32 reviews
11 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Shatoria was great. She engaged my two pups quite a bit. I received lots of photos of happy dogs, some cuddling with her - a good sign! The house was in excellent order, just as I left it. I plan to invite her to house/dog sit again. Thanks Shatoria!

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Marit S.
Sitter Profile Image: Tatyana K.
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Tatyana K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
70 reviews
23 repeat clients
4 years of experience
Fitchburg, WI, 53713

Tatyana is a reliable and caring sitter. She stayed at our house with our 11.5-year-old German Shepherd and provided excellent care, and tremendous peace of mind for us. Having worked at a kennel previously, she is comfortable around all types of dogs (and ours is a big boy). She sent periodic updates and followed our instructions well. We highly recommend her for short or extended care.

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Marlys M.
Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
42 reviews
13 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

Elizabeth was amazing with my dog while I was traveling for work. She sent daily updates and many pictures. I would definitely use her services again.

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Fernanda R.
Sitter Profile Image: Jesse T.
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Jesse T.
Star Sitter
from
$28
per night
5.0 out of 5 stars
18 reviews
10 repeat clients
1 year of experience
Madison, WI, 53719

We had an amazing experience with Jesse! She took wonderful care of both our dog and our cat while we were away for two weeks. She was incredibly attentive, super kind with our pets, and clearly loved spending time with them. She even surprised our dog with some plush toys before she left, which meant so much to us. When we came back, both of our pets were completely relaxed and happy, which says everything about the level of care they received. On top of pet care, she was a huge help with things around the house when they came up and shared really helpful advice for managing our dog’s allergies. We truly felt supported the entire time we were away. We couldn’t be happier with her care and will absolutely be booking her again for our next trip. Highly recommend.

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Seb A.
Sitter Profile Image: Emma W.
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Emma W.
from
$45
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
5 years of experience
Cottage Grove, WI, 53527

Emma was absolutely fantastic with our large dogs! They are a bit high maintenance in their own ways but they were taken care of perfectly! Will absolutely be booking again in the future!

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Young A.
Sitter Profile Image: Louisa S.
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Louisa S.
from
$70
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
15 years of experience
Sun Prairie, WI, 53590

Louisa was excellent! She was so thorough in our meet and greet making sure she was aware of any and all needs Ollie might have. Ollie loved her right away which made me feel very comfortable. Louisa was great at communicating and sent pictures during the sit which I appreciated. Highly recommend her and will certainly have her care for Ollie in the future!

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Angi K.
Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$68
per night
5.0 out of 5 stars
37 reviews
4 repeat clients
20 years of experience
Deforest, WI, 53532

Becca does such a great job with my senior lab. She takes care of all my dog’s needs and she is always excited to see Becca. She also does a wonderful job communicating and keeping me informed about how the days are going.

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Angela S.
Sitter Profile Image: Ayomi O.
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Ayomi O.
from
$40
per night
2 years of experience
Madison, WI, 53704

About: Hi! I’m Ayomi, and caring for animals has always been a natural part of who I am. I’ve had the joy of working with dogs of all ages and personalities from energetic puppies still learning the world to older dogs who move a little slower and need some extra love. I approach pet care the same way I would care for my own patient, present, and with a whole lot of heart. I take the time to learn each dog’s unique needs and routines because I know how important it is for pets to feel safe and comfortable while their people are away. Whether your dog needs long walks, gentle play, quiet companionship, or help with medication or anxiety, I’m here to meet them where they are and give them the attention they deserve. I truly love building trust with both pets and their humans. You can expect regular updates, happy photos, and the reassurance that your pup is in loving, capable hands. Every visit is a chance to create a little joy and comfort for your furry friendcand that’s a responsibility I take seriously and gratefully. Pet care fits naturally into my routine because I often work from home in my downtown Madison apartment. I love taking long walks around town or heading to Picnic Point for a quiet hike, so having a pup along for the journey just makes it that much better. I usually walk about a mile or two a day, but I’m happy to adjust based on your furry friend’s energy level and needs. My schedule is flexible, and with at least a week's notice, I can make sure I’m fully available to give your dog the time and attention they deserve. I’ve always loved traveling, so pet sitting is a fun and fulfilling way for me to enjoy the company of dogs while I’m still settling down. Whether it’s a weekend stay or daily walks, I’m excited to share my time! Creating a safe and comforting environment is my top priority, whether I’m caring for your pet in my home or yours. I treat every dog like family—with patience, attentiveness, and a whole lot of love. In my downtown apartment, pets are kept in a clean, calm space free of hazards, with plenty of room to stretch, nap, or play. I don’t have any other pets, so your dog will get my full attention and care without distractions. When I’m in your home, I’m always respectful of your space and routines, making sure your dog stays comfortable in their familiar surroundings. I follow all care instructions closely and provide regular updates so you know exactly how your pup is doing. I believe trust is built through consistency, communication, and genuine care and that’s what I bring to every visit. Whether it’s daily walks, overnight stays, or just keeping your pup company, I’m committed to making sure your dog feels safe, loved, and right at home.

Sitter Profile Image: Pam W.
Verified Enhanced Background Check
Pam W.
from
$75
per night
5.0 out of 5 stars
30 reviews
8 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Once again, Pam is the best sitter we could ask for. She is so kind, patient, and understanding of our shy rescue, providing him with love and care while respecting his boundaries. She is wonderfully communicative and we were able to enjoy our trip fully knowing our pup was in good hands.

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Emily G.
Sitter Profile Image: Alicia D.
Verified Enhanced Background Check
Alicia D.
Star Sitter
from
$70
per night
5.0 out of 5 stars
95 reviews
24 repeat clients
7 years of experience
Lodi, WI, 53555

Alicia stayed with our dog Hazel for a long weekend and we will definitely book her again! Hazel sometimes struggles to warm up to new people but she loved Alicia immediately during our meet & greet. Alicia asked lots of good questions to make sure she was prepared to care for Hazel, and she sent us photos every day.

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Elise & Kyle
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Over 78
pet parents in Windsor have booked house sitting

Windsor pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Tiana did a great job taking care of our dog! She was friendly, reliable, responsive to our additional requests, and even sent photos so we could feel connected while we were away. I would definitely hire her again.

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Nicole H.
House Sitting
5.0 out of 5 stars

Rebecca did an incredible job taking care of our two elderly pups, one of which was going through a rough time medically, and required bathroom breaks during the night. Without her care, compassion, and attentiveness, I don’t know what we’d do! She is truly a godsend!

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Sara E.
House Sitting
5.0 out of 5 stars

Tina always does a great job with our dogs. She sends us updates every day which is nice to see. We would recommend her to anyone!

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Lindsey B.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Windsor is $50

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Windsor average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windsor on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Windsor house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 766 house sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 89% of Windsor house sitters respond in under an hour.

House sitters in Windsor have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windsor.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windsor house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.