House Sitting in Woodland

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

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Top rated Woodland 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: Meghan A.
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Meghan A.
from
$60
per night
5.0 out of 5 stars
31 reviews
9 repeat clients
20 years of experience
Rubicon, WI, 53078

As first time Rover users, Meghan completely put our worries at ease and took the best care of our fur babies during the weekend of our wedding. I loved getting my picture updates of the pups knowing they were in the comforts of their familiar surroundings being cared for by somebody that knew what they were doing instead of being in a high stress environment. The dogs loved her too! We will 100% be using Meghan again in the future when we go on our honeymoon.

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Amanda B.
Sitter Profile Image: Lyla H.
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Lyla H.
from
$50
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Iron Ridge, WI, 53035

About: My family has had a dog since I was younger and I currently have a mini goldendoodle. I understand how keeping dogs happy and cared for is vital to ‘owners.’ I have a very flexible and open schedule! I like to take my own dog for longer walks to get energy out and relax our minds together. I love playing with them so they’re not just sitting around unhappy. It’s important to me to make sure all of their needs are met as I believe this affects longevity and overall well-being.

Sitter Profile Image: Courtney Z.
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Courtney Z.
from
$50
per night
4.9 out of 5 stars
8 reviews
1 repeat client
8 years of experience
Hartford, WI, 53027

Courtney was very sweet and responded quickly to messages. There was a misunderstanding with her work schedule that she would not be in the home for 11 hours. I assumed she would come at lunch to let them out. Never assume - had to call neighbor to let dogs out 2 days as I did not want my dogs left that long without a potty break. Otherwise, all was good.

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Cindy L.
Sitter Profile Image: Kristin C.
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Kristin C.
from
$50
per night
5.0 out of 5 stars
37 reviews
10 repeat clients
10 years of experience
Watertown, WI, 53094

Thank you so much for taking care of our puppies! We loved the pictures :-) they seemed very happy when we got home! Please come watch them again!

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Lizzy T.
Sitter Profile Image: Haydn H.
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Haydn H.
from
$60
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
8 years of experience
Ixonia, WI, 53036

Haydn did a great job with my pup. She spent a ton of time with her playing and taking her on walks. I got updates and pictures throughout the time period. The house was in great shape when I got home and and very clean. I would definately recomment Haydn and use her again!

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Angela N.
Sitter Profile Image: Katy Z.
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Katy Z.
from
$50
per night
1 repeat client
20 years of experience
Neosho, WI, 53059

About: I have one or two dogs since I was a little girl. I currently have 2 rescues who I love very much! I have helped watch neighbors dog a few times, and now Would like to make some money doing what I love. Dogs are absolutely man’s best friend. I could never live without a dog in my life. I currently work full time, I work until 4 M-F. I am available on the weekends to do drop in care, dog walking or overnights I would care for dogs in your home, and make sure their every need is taken care. I will treat them like my own. I am willing to walk, bath, snuggle ,and give them my full attention

Sitter Profile Image: Ella S.
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Ella S.
from
$40
per night
6 years of experience
West Bend, WI, 53090

About: I've taken care of animals my entire life. I've always had dogs, cats, reptiles, small animals, you name it! I have been picking up gigs dog/cat sitting since I was 12. My family, friends, and neighbors have had my help and continue to use me as their first option when help is needed! I'd love to get to know your furry friend :) I currently work part-time from 5pm-10pm Monday thru Friday for the summer, so I am available to spend the morning and midday's playing, feeding, walking, and watching your pet! I have 2 dogs (large and small) and 4 cats of my own. With this, I won't offer in home care due to the stress this can cause your pet. However, I am comfortable with leashing, caging, giving meds, scooping liter pans, and all other responsibilities that come with pet care!

Sitter Profile Image: Victoria K.
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Victoria K.
from
$25
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Oconomowoc, WI, 53066

Victoria did a great job taking care of our dogs. Was also very good at sending photos and communicating. Would definitely recommend!

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Analisia W.
Sitter Profile Image: Rebekah B.
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Rebekah B.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
4 years of experience
Watertown, WI, 53098

Rebekah stayed with our 4 dogs and 1 cat this past weekend and honestly everything went perfect! Our dogs and cat were very well taken care of and our house looked as though she never stayed. She was very prompt with updates throughout the weekend and gave our fur babies so much love! We will be using her again in the future and would highly recommend!!

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Julie G.
Sitter Profile Image: Lindsey L.
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Lindsey L.
from
$85
per night
5.0 out of 5 stars
1 review
1 repeat client
18 years of experience
Watertown, WI, 53094

About: I have been a CVT for 18 years, actively working at an emergency/specialty clinic. I can care for all ages and sizes of dogs and cats. I have a part time job that is flexible, my main focus is pet care and services. I am available most days and hours. I am pet sitting or caring for pets on a daily basis. I will utilize your house to care for your pets so they are more comfortable and less stressed. I will follow your daily routines to keep them feeling secure.

Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$60
per night
5.0 out of 5 stars
25 reviews
10 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Katelyn watched my English Bulldog and Chocolate Lab while I was on vacation for several days. She took great care of my fur babies. She fed them, walked them, let them out several times, and gave them loves and pets. She sent good notes and several pictures and videos throughout the stay.

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Danielle R.
Sitter Profile Image: Michael R.
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Michael R.
from
$28
per night
5.0 out of 5 stars
2 reviews
1 repeat client
30 years of experience
Menomonee Falls, WI, 53051

Michael had been wonderful and he has helped us out with our two dogs several times. He communicates well and my dogs have been so happy having him stay with them while we are gone. Would recommend him to take care of your pets.

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Janine P.
Sitter Profile Image: Cindy S.
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Cindy S.
from
$55
per night
5.0 out of 5 stars
50 reviews
14 repeat clients
45 years of experience
Oconomowoc, WI, 53066

Cindy was great! Great communications and took excellent care and attention to my dog while I was away. Valentine got daily walks and play time; the pictures sent to me was very reassuring.

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Merry C.
Sitter Profile Image: Trinity P.
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Trinity P.
from
$27
per night
8 years of experience
Burnett, WI, 53922

About: Hi ! As I am home for summer , I would love to be able to watch any animals , any size is okay ! I have grown up with large dogs most of my life but I am okay with any size and age. I am a college student athlete at Winona State University going into my Junior year next semester! I am also a nanny in the summers so I am very flexible when it comes to times or days ! I am also a nanny in the summer which means I have can have very flexible hours ! I am also very active, walks, runs etc. I have a fenced in yard and a pool ! But also I have a dog and my mom has a dog they are both loving and will keep your animal company!

Sitter Profile Image: Amy H.
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Amy H.
from
$70
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
40 years of experience
Hubertus, WI, 53095

Gave updates and gave Libby her meds as scheduled :)

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Tracy C.
Sitter Profile Image: Elizabeth C.
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Elizabeth C.
from
$40
per night
40 years of experience
Oconomowoc, WI, 53066

About: I have cared for animals my entire life and truly believe they are part of the family. Over the years, I’ve had hands-on experience with many different types of pets, including cats, dogs, birds, horses, chickens, rabbits, guinea pigs, amphibians, and more. Animals are my passion, and caring for them genuinely brings me joy. Whether it’s providing companionship, playtime, feeding, or making sure they feel safe and comfortable while you’re away, I treat every animal with the same love and attention I would give my own pets. You can feel confident knowing your pet will be cared for by someone who is experienced, attentive, and truly loves animals. Pet care fits very naturally into my daily routine, and I prioritize making sure animals receive attentive and reliable care. I am currently available during the day, which allows me to be flexible and attentive to your pet’s needs. On weekdays, I do drop off and pick up my two children from school (ages 8 and 10), but outside of those short times my schedule is very open. This allows me to provide consistent care, visits, playtime, feeding, and companionship for your pets. Because I structure my day around the animals I’m caring for, you can feel confident that your pet will receive dependable attention and thoughtful care while you’re away. I prioritize safety, comfort, and trust when caring for pets, whether they are in my home or their own familiar environment. My home sits on nearly one acre with an unfenced yard, which allows for plenty of outdoor play and exercise. Dogs can enjoy time outside on leash, and off-leash play can be discussed depending on the dog’s training and owner preferences. Inside my home, my own pets have separate spaces, which allows visiting animals to be safely and comfortably separated if needed. This helps ensure a calm and secure environment for everyone. I am also happy to care for pets in their own homes. I am very respectful of clients’ homes and always follow instructions carefully to maintain your pet’s normal routine. Whether in my home or yours, I provide attentive care including feeding, playtime, companionship, exercise, and administering medications if needed. My goal is always to make pets feel safe, comfortable, and well cared for while you are away.

Sitter Profile Image: Bella B.
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Bella B.
from
$63
per night
5.0 out of 5 stars
34 reviews
14 repeat clients
15 years of experience
Watertown, WI, 53094

It was so nice to have Bella cat/house sit for us on our recent trip. So comforting to know our cats had a person to spend time with in the evenings and give them lots of attention. She also left our place super clean! Would definitely ask back. Thanks Bella!

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Kelly S.
Sitter Profile Image: Anna H.
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Anna H.
from
$85
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
12 years of experience
Hartford, WI, 53027

We enjoyed Anna sitting for cats and house again. Her obvious love of animals, diligent caretaking, attention to detail, and solid communication put our minds at ease while traveling. Looking forward to her next stay!

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Trish W.
Sitter Profile Image: Hannah S.
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Hannah S.
from
$55
per night
5.0 out of 5 stars
44 reviews
16 repeat clients
20 years of experience
Hartford, WI, 53027

Hannah took excellent care of our dog. She came over multiple times each day for walks, feedings and play time. I loved the daily updates and pictures

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Colleen J.
Sitter Profile Image: Rowan B.
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Rowan B.
from
$40
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Waukesha, WI, 53188

Our Chunks loved hanging out with Rowan! He got lots of excersize, love, and play time and is now sleeping peacefully because he had so much fun! Definitely will be using her again!

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Naomi N.
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The median cost per night for house sitting in Woodland is $50

Why Choose Rover?

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  • 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 Woodland average 3
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 Woodland 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 Woodland 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 223 house sitters in Woodland. 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, 85% of Woodland house sitters respond in under an hour.

House sitters in Woodland have an average of 18 years of experience. House sitters with repeat customers have an average of 3 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 Woodland.

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. Woodland 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.