House Sitting Woodland

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Sitter Profile Image: Courtney Z.
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Courtney Z.
from
$50
per night
4.9 out of 5 stars
10 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: Meghan A.
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Meghan A.
from
$60
per night
5.0 out of 5 stars
32 reviews
9 repeat clients
20 years of experience
Rubicon, WI, 53078

Meghan was wonderful! She put up with our naughty little dog and two pups. She kept us up to date and was very informative. We will be using her again! Wonderful.

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Michele V.
Sitter Profile Image: Kendra M.
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Kendra M.
from
$42
per night
5.0 out of 5 stars
6 reviews
3 years of experience
ixonia, WI, 53036

Kendra was amazing with my dog Winter! She was a great house guest and cleaned up after herself and beyond. I got several pictures of Winter and prompt replies when I would check in. I will definitely use her every time I need someone to come stay.

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Stephanie J.
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 was amazing with our boys! I am so thankful for the great care she gave them while we were away, and will definitely book again the next time we need a dog/house sitter!

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Ashley H.
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

Outstanding communication and treated the dogs like if they were her own. The house was clean and orderly we would definitely love to have her back again.

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Brenda S.
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 Is the ideal cat sitter. I wanted to not have to worry about Baby Bear having a clean litter box and eating his wet and dry food. Cindy was there for him and he’s happy! That’s what a great pet sitter does.

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Larry B.
Sitter Profile Image: Josilyn M.
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Josilyn M.
from
$27
per night
5 years of experience
Beaver Dam, WI, 53916

About: Give your dog a fun 30-minute walk around town or on a local trail. I welcome multiple dogs, and every walk provides exercise, exploration, and mental enrichment. ( and some yummy treats ) My 30-minute pet check-ins provide potty breaks, meals, walks, and quality playtime, ensuring your furry friends stay comfortable and loved while you're away. Pictures are included with each walk/visit! I have worked in a dog daycare/boarding facility for the past 3 years with dogs of all sizes and breeds. I have over 5 years of experience with dogs of my own. I spend lots of time taking them on walks and hikes. I have experience to care for your senior pups and administering medication, as well. My favorite thing to is walk dogs and I can work with your pup on leash manners. I am also open to working with aggressive and/or reactive dogs. Can't wait to meet some new furry friends! I work a full time job about 30 hours a week. I am looking to walk/sit your pets in the evenings and some weekday/weekend availability depending on my hours. I am also open to holiday care. I won't be offering care in my home, but I will carefully follow all of the care instructions for your pups and cats and be sure to send you updates on the visits/walks.

Sitter Profile Image: Emma R.
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Emma R.
from
$45
per night
5.0 out of 5 stars
5 reviews
10 years of experience
Pewaukee, WI, 53072

About: I've lived with animals my entire life. Growing up, we had five dogs, four cats, bunnies and guinea pigs, snakes and lizards, fish, and chickens. Currently, while living at home in the summers, we have snakes, lizards, spiders, a cat, and three dogs, one of which is mine. My dog Winston is a service dog in training that my mom and I are owner-training. While I'm in no way a professional trainer, I can help with teaching or maintaining the basics with any dog. I'm currently home for the summer from school and waiting on an application for a part-time job. I am free most of the day right now, as I haven't started working yet. So, I can come over and take care of any pet's needs most any time. I can take care of your animals' needs any time, whether it's taking them on a walk, letting them outside, feeding, cleaning up, or playing with them. My dogs at home are crate trained, so if your dog also stays in a crate at certain points of the day or night, I can easily crate them.

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: Katelyn W.
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Katelyn W.
from
$60
per night
5.0 out of 5 stars
28 reviews
12 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Have used Kate multiple times to stay with our pets and our house. She does a great job and is super respectful of the space. Will continue to use her in the future.

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James F.
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: 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: Victoria K.
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Victoria K.
from
$25
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Oconomowoc, WI, 53066

Victoria took great care of our pups! She sent lots of pictures and kept us updated.

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Katelyn W.
Sitter Profile Image: Bella H.
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Bella H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
19 reviews
6 repeat clients
13 years of experience
Menomonee Falls, WI, 53051

Bella did an amazing job pet and house sitting for us while we took a short getaway for three nights. She was communicative throughout - which eased our minds as we had recently adopted one pup and this was our first time away. Our dogs - and cat! - were obviously well cared for upon our return, and Bella left the house in perfect order. Would easily recommend anyone to book her, and we hope she'll come back when we take our next adventure!

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

Bella was a great communicator, did a wonderful job watching our two dogs. She left the house in perfect condition after house sitting for 4 nights. She even did the laundry and cleaned up when one of our dogs had an accident on the couch. She was wonderful!

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Jared B.
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: Olivia C.
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Olivia C.
from
$25
per night
10 years of experience
Oconomowoc, WI, 53066

About: I have raised and cared for many animals throughout my lifetime ranging from dogs, cats, kittens, cows, raccoons, guinea pigs, bunnies, and fish! There is no animal too big, small, or sassy for me! I love them all! I have experience with bottle fed, new born animals, pets with different feeding patterns in the same house, delivering medicine to pets (including via syringe), outdoor supervision, and caring for temperamental animals. My own dogs are a pitbull and Doberman respectively, so I know firsthand that a breed or size does not define an animal! I am here to provide exceptional care to your fur babies regardless of shape, size, age, or attitude! I work various part-time jobs around the Mount Horeb/Middleton area, but would almost always be available for morning, afternoon, and evening care! If planned a few days in advance, I can accommodate most needs! I believe in following instructions carefully, especially when it comes to animals. While I strive to create a relationship with the animals I care for, my main priority is to listen to the advice and instructions of the pet parents to ensure I am prepared and aware of their pet’s unique characteristics and needs. Nobody knows an animal like their owner, and I am dedicated to doing as told when it comes to animals—especially considering the trust the owners have in me!

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: Jessica R.
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Jessica R.
from
$40
per night
4.8 out of 5 stars
14 reviews
4 repeat clients
20 years of experience
Hartford, WI, 53027

About: I am an animal lover and will take great care of your pet. I have experience owning dogs and currently own a 5 year old Doberman Pinscher named Moon. I am extremely active and love to take dogs on walks, to the park to play and outside to get fresh air. Having experience volunteering at the humane society, I am aware of different pet personalities and cautious of their well-being and comfort. I will honor the owner's rules and routines in order to make the experience positive for all parties involved. I live in an area great for walking dogs and running them with toys. If the pet needs extra attention or additional exercise, I will be able to accommodate with my flexible work schedule. Thanks!

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

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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Woodland average 3
repeat house sitting clients

FAQs for House Sitting - Woodland

Frequently asked questions about Rover

As of June 2026, there are 447 sitters on Rover offering House Sitting across Woodland. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Woodland walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Woodland maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Woodland choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Woodland. On Rover:

  • 100% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 100% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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