House Sitting In Westchester Gardens

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

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Top rated Westchester Gardens 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: Robert L.
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Robert L.
Star Sitter
from
$44
per night
5.0 out of 5 stars
262 reviews
50 repeat clients
40 years of experience
Capitol, Madison, WI, 53703

Robert housesat with our 2 dogs and was fantastic with the pups and as a houseguest. He worked so well with our pups and their personalities. Robert's communication is very helpful and reassuring. I was "at peace" during our entire trip away because he sent regular updates and stayed in touch during our travel days. Robert is very professional, communicative, and so good with animals. You can tell he really does this for the joy he gets taking care of your pets. You will not be sorry if you book Robert!

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Kathryn (Kate) H.
Sitter Profile Image: Samantha M.
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Samantha M.
from
$45
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Madison, WI, 53704

Samantha is a very good worker. She is very responsable and she is always on time. She took care of Rokko very well and Rokko was very happy since the first moment. We appreciated her work very much.

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Sonia M.
Sitter Profile Image: Amanda S.
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Amanda S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
27 reviews
14 repeat clients
12 years of experience
Madison, WI, 53713

Good communication and appropriate check ins. Handled being accidentally locked out very well when the battery to my keypad lock died. Would book again.

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Amanda M.
Sitter Profile Image: Elizabeth K.
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Elizabeth K.
Star Sitter
from
$40
per night
5.0 out of 5 stars
33 reviews
8 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

Elizabeth was wonderful with Ollie! He took to her right away. She sent lots of pics which I appreciated! She also took great care of my home. Would highly recommend!!

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

Cassandra was great! So nice to have someone stay with Leo while we were gone. Way less stressful for him and us. Thanks Cassie, we’ll be rebooking for our next trip!

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Matthew B.
Sitter Profile Image: Kirsten R.
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Kirsten R.
from
$50
per night
4.9 out of 5 stars
23 reviews
5 repeat clients
6 years of experience
Madison, WI, 53718

This was my first time leaving my dog and cat and Kirsten did an amazing job! She sent tons of pictures and updates while I was gone. She left my house spotless and got the mail while I was gone. I highly recommend Kirsten to watch your fur babies! I’ll definitely ask her to watch mine again in the future!

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Lindsey M.
Sitter Profile Image: Isabel S.
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Isabel S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
21 reviews
7 repeat clients
15 years of experience
Midvale Heights Community, Madison, WI, 53711

Isabel is definitely a 5-star sitter. Sent pictures daily of our dog, followed all directions left for her. She went above and beyond caring for our dog who needed daily medication. Great communication. Sadie was somewhat shy at first but it didn’t take long to warm up to Isabel. Definitely recommend and will rebook her as needed.

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Linda H.
Sitter Profile Image: Sylvia L.
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Sylvia L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
8 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: Autumn J.
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Autumn J.
from
$65
per night
5.0 out of 5 stars
9 reviews
1 repeat client
4 years of experience
Madison, WI, 53704

Autumn took great care of my dogs. She was prompt, communicative and tidy. The dogs were relaxed and happy when I got home.

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Heidi S.
Sitter Profile Image: Leah B.
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Leah B.
from
$55
per night
4.7 out of 5 stars
87 reviews
33 repeat clients
6 years of experience
Monona, WI, 53716

Leah you were amazing. Thank you for your flexibility and quick responses. I felt so comfortable leaving my giant boys with you. I can tell they felt very comfortable. We really appreciate you!

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Allison S.
Sitter Profile Image: Sara N.
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Sara N.
from
$75
per night
5.0 out of 5 stars
12 reviews
8 repeat clients
11 years of experience
Madison, WI, 53704

Sara watched our house and animals for a week and we could not have been happier. They did a great job and were very communicative, even coming back to check on the dogs when our flight was delayed. I would absolutely have them back any time!

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Kristen R.
Sitter Profile Image: Travis M.
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Travis M.
from
$70
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
15 years of experience
MONONA, WI, 53713

Travis did a great job, the house is clean, Pearse is happy and well taken care of. We so appreciate how Travis thinks ahead and goes way above and beyond!

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Mary V.
Sitter Profile Image: Jesse T.
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Jesse T.
Star Sitter
from
$28
per night
5.0 out of 5 stars
11 reviews
6 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: Isaac T.
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Isaac T.
Star Sitter
from
$35
per night
4.9 out of 5 stars
15 reviews
6 repeat clients
5 years of experience
Cottage Grove, WI, 53527

Isaac was very good with our critters, including our 20 year old cat. The dogs seemed to have a great time too. He was considerate with the house, cleaning up after himself and brought in a package that was delivered early without me needing to ask. We would rebook with Isaac.

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Michelle M.
Sitter Profile Image: Karina M.
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Karina M.
from
$32
per night
5.0 out of 5 stars
24 reviews
6 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

We were very pleased with Karina house sitting for us! She asks about specific commands, dietary needs, and preferences of our dog, which was incredibly sweet and thoughtful. She also provides detailed updates and appears to really adore and read pup personalities well. We would highly recommend Karina and will definitely reach out to her again!

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Na L.
Sitter Profile Image: Kristina G.
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Kristina G.
from
$30
per night
5 years of experience
Marquette, Madison, WI, 53704

About: I have lived with large dogs my entire life and own 2 cats of my own, one of which I take for walks outside on a leash every day. I am responsible, communicative, and compassionate. Pet happiness is very important to me! I am currently unemployed so my time is very flexible, both during the week and weekends. I am usually unavailable Friday afternoons but that can be flexible as well I love caring for animals in the way that clearly makes them feel safe and happy whether it is the smallest, weirdest, or most random things. I am happy to tailor the experience to each individual pet and their owner, and take safety and communication very seriously as that is what I would want for my cats

Sitter Profile Image: Tina B.
Verified Background Check
Tina B.
Star Sitter
from
$35
per night
4.9 out of 5 stars
75 reviews
22 repeat clients
38 years of experience
Waunakee, WI, 53597

We had Tina meet our dogs to make sure she would want to do it. We have a needy Bulldog and a protective Mix. By the time Tina left our house, the dogs were great with her. She sent pictures and updates on the dogs daily and everything they were bothering her with, they bother our family with when were home. So we knew the dogs were comfortable. We will definitely seek out Tina in the future.

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Tanya O.
Sitter Profile Image: Jessa E.
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Jessa E.
from
$40
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
3 years of experience
Madison, WI, 53714

12 out of 10. Jessa truly saved me with a last minute request after I had a few rover sitters canceled on me. She came and met my dogs and also was gracious enough to keep an eye on my garden. I will absolutely be using her in the future.

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

Emma was communicative, kind, and took great care of our dogs while we were away!

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Valerie W.
Sitter Profile Image: Maria & Bryan P.
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Maria & Bryan P.
from
$35
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
30 years of experience
Waunakee, WI, 53597

About: We have been loving and caring for dogs for a long time. Big and small dogs; young and old. Our son and 7 year old dog are welcoming I am currently working from home and Bryan works part time. Our son is home schooled at this time, therefore, we have time and energy to help other dogs and other families We have a large yard in a quiet neighborhood; part of our yard is fenced and other part is open for additional exercise. We also walk our dog daily.

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Westchester Gardens pet parents share their Rover experiences

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5.0 out of 5 stars

Adeline watched our dog Ruby during an overnight visit in our house. She went above and beyond in communication by sending text and picture updates and we felt confident Ruby was very safe in her hands. We will definitely book Adeline again!

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Kayla A.
House Sitting
5.0 out of 5 stars

We couldn’t have asked for a better pet sitter! Kirsten watched our cat for 11 days, providing both drop-in visits and overnight care, and went truly above and beyond. She spent lots of time with him, played with him often, and kept us updated with frequent messages, pictures, and videos — which gave us so much peace of mind while we were away. Our cat looked completely comfortable and happy in her care, which says a lot! She was always quick to respond and so easy to communicate with. We would absolutely recommend her to anyone looking for a reliable and attentive pet sitter.

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Bliss G.
House Sitting
5.0 out of 5 stars

Katie was wonderful! She kept me updated and all of my pets were well taken care of. I appreciated it so much especially since it was a last minute booking. I will definitely be booking Katie again.

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April W.
House Sitting
5.0 out of 5 stars

This was our first time having a dog sitter stay with our 2 dogs, one of which is highly anxious. Needless to say we were also feeling nervous about it, but Sylvia was a gem. Before our trip she was willing to come by several times to let our dogs familiarize themselves with her so by the time it came to our trip, the dogs felt like they were just seeing a friend, not a stranger. Sylvia sent daily updates/photos. It was such a relief to know our dogs were being well taken care of which also allowed us to relax and enjoy our trip.

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Whitney E.
House Sitting
5.0 out of 5 stars

Oliver did an excellent job taking care of our dog! Great communication while we were away and sent lots of cute pictures.

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Keelin M.
House Sitting
5.0 out of 5 stars

Cassandra was very communicative and helpful while we were gone and our dog had health issues. We would book with her again!

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Olivia M.
House Sitting
5.0 out of 5 stars

Joshua did such a great job caring for our home and animals while we were away on a long trip. We loved all the pictures and felt so reassured knowing he was there to take care of things!

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Emily H.
House Sitting
5.0 out of 5 stars

Scott really helped us out with a week of drop-in visits for our two dogs, one of which is rather unpleasant with strangers. He also agreed to oversee our coop of chickens which was very helpful. Scott was accomodating and generally a good communicator, and the pups seemed to like him. I think he did a fine job. We would definitely work with Scott again.

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Jessy P.
House Sitting
5.0 out of 5 stars

Elizabeth was stellar from start to finish--we booked her last minute and she was responsive, punctual, generous with her time, and very sweet with our dog. We received regular updates and check-ins, and Lizzie rolled with the situations like a pro. She even checked on M in the evenings, after the afternoon walk. It was honestly such a relief to know our dog was with someone who could pivot with the situation--including giving meds, taking M to daycare, and being patient during the first visit when M barked and growled. M is a livestock guardian dog, and Lizzie successfully worked with our sweet girl’s personality. Reccommend!

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Anna S.
House Sitting
5.0 out of 5 stars

I couldn’t have asked for a better dog watcher! Jess was extremely responsive and communicative from the start, which gave me so much peace of mind while I was away. When I came home, not only were my dogs happy and well cared for, but my house was also clean and tidy—such a thoughtful touch. What really stood out was how much effort she put into getting to know my dogs. It was clear she genuinely cared about their personalities, routines, and comfort. She truly went above and beyond in every way. I would absolutely trust her again and highly recommend her to anyone looking for reliable, attentive pet care.

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Shana W.
House Sitting
5.0 out of 5 stars

This is the second time Nia and Lauren have stayed with Fred. We again feel great about how they treat our doggie and our home. Highly recommend.

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Mary R.
House Sitting
5.0 out of 5 stars

I appreciated that Lora was communicative. Best sign of a good sitter ㅡmy kitties were happy when I returned.

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Michelle R.
House Sitting
5.0 out of 5 stars

Alicia is such a special person. She loves our little complicated Chihuahuas and they love her!! So grateful!!! 💙💗

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Cara M.
House Sitting
5.0 out of 5 stars

Edwin was a great dog sitter for Cosmo. He communicated with us very promptly and often. He sent pictures a few times a day and Cosmo always looked happy and content. Edwin left our house clean and in order. We would happily have him to take care of Cosmo again!

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Jeannette L.
House Sitting
5.0 out of 5 stars

Megan is always reliable and communicative and most importantly keeps our dogs safe and happy :) appreciate you!!!

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Meghan F.
House Sitting
5.0 out of 5 stars

Phenomenal to our fur babies. Very responsive and helpful at short notice. Will definitely use again!

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Rob H.
House Sitting
5.0 out of 5 stars

Raven was wonderful. We appreciated all the pictures and communication that helped us to know that Hunter was in good hands. Hunter made friends with her right away. We felt confident that Hunter and our home were being well taken care of.

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Gary B.
House Sitting
5.0 out of 5 stars

Mallory did a great job, she texted me almost everyday with updates, she kept the house clean and tidy and most of all gave our fur babies lots of love.

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Julie G.
House Sitting
5.0 out of 5 stars

Samantha did a great job. My dogs seemed happy when I got home. I definitely would love for her to babysit for us again!

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Julie M.
House Sitting
5.0 out of 5 stars

Natalie took great care of my senior lab Walter over the holiday. We really appreciate the updates, communication, and her availability on short notice. Thanks again Natalie!

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John D.
House Sitting
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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!

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.

House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Westchester Gardens 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.

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

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Westchester Gardens.

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. Westchester Gardens 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.