House Sitting Drywood

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

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Over 9
pet parents in Drywood have booked house sitting

Drywood, Find top rated house sitting

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: Carissa N.
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Carissa N.
Star Sitter
from
$28
per night
5.0 out of 5 stars
233 reviews
81 repeat clients
18 years of experience
Cadott, WI, 54727

Carissa did a great job of taking care of my 2 dogs and cat while we were on vacation. I didn’t worry about them at all, which never happens when I am away. Thanks

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Jan M.
Sitter Profile Image: Jill J.
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Jill J.
from
$60
per night
5.0 out of 5 stars
1 review
45 years of experience
Cornell, WI, 54732

About: My goal is to create a stress-free experience for both pets and their owners by offering dependable, compassionate care. I have experience providing reliable and attentive dog sitting services for a variety of breeds. I am comfortable with feeding schedules, administering basic medications, daily walks, playtime, and maintaining consistent routines to help dogs feel safe and comfortable while their owners are away. Rest easy that your furbaby will be loved on and cared for as if he/she were my own. I currently work full time and am gone 8-9 hours a day Monday through Friday but weekends are for relaxing. If weekday care is needed I am available and can arrange for a mid-day potty break. But the weekends are all about your pet. Walks, parks, car rides (for those who love them), catch, fetch and snuggles. I do not have a fenced yard so require adequate leash/collar for walks and potty breaks. My neighborhood is very friendly and safe and I live one mile from a State Park for more open space if your pet is good off leash. There are no children in my home. It is one level with a basement that can be closed off. I do not mind pups in my bed or on my furniture- as long as they are pest free and clean.

Sitter Profile Image: Kaitlynn S.
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Kaitlynn S.
from
$80
per night
5.0 out of 5 stars
3 reviews
1 repeat client
14 years of experience
Boyd, WI, 54726

About: I have been relied on to care for friends, family, and neighbors pets since I was old enough to take responsibility. When I was 14, my helping of peoples pets started when I watched a family friends dog for 4 years during week days and occasional weekends. I worked at a doggie day care facility for 4 months at the end of 2021, doing all duties that go into caring for our furry friends. I went to college to get a degree as a Veterinary Technician for a year and a half. During the time of schooling I worked in a vet clinic and took on the job role as a kennel technician, helping out with anything and everything I could get my hands on. I dropped school because of personal and external obstacles but would love to go back in the future to finish. I only aim to please and never disappoint! Please choose me to be your pets new best friend! I'm currently working full time in Gilman WI, Mon-Thurs 630AM-4PM, Fri 630AM-1030AM. I am mostly available during weekends. The earlier you book with me, the better. I like to plan ahead. I try to be flexible and fit in your pet sitting needs! When caring for pets in a clients home, I am sure to make sure that I am careful when first meeting animals as I know it could be dangerous because of their protectiveness. I make sure to look over instructions twice, and double check that all to-dos are completed before leaving the clients home. I make sure to potty before I leave each time to avoid messes and make sure that they get exercise/attention during my time with them, as I know they feel down without someone home with them.

Sitter Profile Image: Allison P.
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Allison P.
from
$75
per night
5.0 out of 5 stars
6 reviews
5 years of experience
Chippewa Falls, WI, 54729

Very friendly and super responsive. Sends an update at with pictures at the end of the day about how well the dogs did. Let me know right away if ran into any issues or questions. I would definitely rebook with her again! 😊

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Ryan E.
Sitter Profile Image: Destiny R.
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Destiny R.
from
$30
per night
5.0 out of 5 stars
20 reviews
4 repeat clients
25 years of experience
Chippewa Falls, WI, 54729

Our experience with Destiny as a sitter at our home was fantastic. She sent lots of photo updates. All the animals, including our shy cat, seemed to love her company! Her communication is excellent and she made sure to check in prior to the stay to make sure we were on the same page for arrival as well as the day/time she left. She cleaned up the house before she left which was not expected at all but very much appreciated. We look forward to having her come back and stay with our fur babies again.

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Katie S.
Sitter Profile Image: Taryn M.
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Taryn M.
from
$35
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
9 years of experience
Eau Claire, WI, 54703

About: Hello, my name is Taryn. I’ve had plenty of experience taking care of dogs as I have had dogs my whole life. Since middle school, I have been pet-sitting for friends, family, and neighbors. Not only have I had pet sitting experience with dogs, I have taken care of other animals as well. Those animals range from cats, bunnies, fish, and even chickens ! I will be able to provide you and your pets with the services you need! I just graduated from UW-Stout and am currently living in Eau Claire. I work at my main job on weekdays (in Menomonie). My hours vary, but they are usually only 7 hour shifts or less. I am available all day on Saturdays and Sundays unless I already have another gig booked. I am able to provide your pet with whatever service they need, ranging from making sure they have enough food and water to taking them on walks and providing them with entertainment! I am available for dog walking and drop-ins before 5pm on Mondays, Wednesday, Friday, and Saturday, and after 5pm Tuesdays and Thursdays. As for house-sitting, I am available most days as long as your pet is okay with being alone for a few hours! I attend in-person classes Tuesdays and Thursdays, but would have an hour or two to come back to the house to check in! I currently do not offer doggy day care in my own home, but I will be able to keep your dogs company at their respective homes. I can walk them, feed them, play with them, keep them company, and more!

Sitter Profile Image: Hadyn H.
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Hadyn H.
from
$100
per night
5.0 out of 5 stars
20 reviews
2 repeat clients
14 years of experience
Chippewa Falls, WI, 54729

About: I have extensive experience and genuine passion for animals. Over the years, I have fostered multiple dogs, dealing with a wide variety of behaviors, breeds, and ages. This hands-on experience has equipped me with the skills to handle any situation and understand the unique needs of each dog. Additionally, I have been dog sitting for family friends and am now excited to expand my services to help others. My love for animals drives me to provide a safe and enjoyable space for your pets, ensuring they have fun and feel secure while you are away. I always love to update owners with pictures of how their furry friends are doing! I seamlessly fit pet care into my weekly routine thanks to my remote work flexibility. This setup allows me to tend to animals whenever needed, ensuring they receive the attention and care they deserve throughout the day. I can easily take pets outside for fresh air and exercise, contributing to their well-being and happiness. Moreover, my schedule has no limitations on the days of the week that I am available, allowing me to offer consistent and reliable care whenever you need it. The environment where I care for pets is ideal for their safety and happiness. I live in the country on a quiet dead-end street with very little traffic, providing a peaceful and secure setting for your furry friends. My active lifestyle means I love to exercise, and I would be thrilled to bring your pet along for walks or runs if they enjoy that. Our home features a big yard perfect for playing and exploring, ensuring your pet has plenty of space to roam. I am dedicated to creating a safe and nurturing environment where animals can thrive while their loved ones are away.

Sitter Profile Image: Celeste G.
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Celeste G.
from
$75
per night
4.9 out of 5 stars
12 reviews
2 repeat clients
1 year of experience
Eau Claire, WI, 54701

Celeste was the greatest! I felt at ease leaving my dogs with her. She was loving and caring and they both loved her! I would recommend her to anyone that has cherished pets.🥰

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Geri F.
Sitter Profile Image: Michelle K.
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Michelle K.
Star Sitter
from
$50
per night
5.0 out of 5 stars
3 reviews
3 repeat clients
50 years of experience
Eau Claire, WI, 54701

About: Hi there! My name is Michelle and Ive been a pet owner since I was a child. My family always had dogs, cats, pocket pets, and the occasional tarantula. Im the niece of a large animal veterinarian whose clinic I volunteered at after school and summers. Currently my husband and I are owned by a Labrador Retriever and an English Setter. We are active with a national English Setter rescue, which is where our beautiful boy came from, and run volunteer transports of dogs on their way to foster or forever homes. *** Due to personal reasons, for House Sitting bookings I sleep at my own home. I will arrange my arrival and departure times at your home, to whatever your preferences are. I usually arrive around 6am and leave between 9 and 10pm, but thats variable based on your pet's routine.*** Im semi-retired! My routine is whatever it needs to be from day to day. Im a firm believer in being flexible to meet the situation's needs. Each pet is different. Some are couch potatoes, some want to hike the Alps, but all need mental stimulation and tons of hugs. Playtime, walks, treats and any other interactions you, as the expert on your pet, request of me, are part of the services I offer.

Sitter Profile Image: Aaralyn A.
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Aaralyn A.
Star Sitter
from
$75
per night
5.0 out of 5 stars
26 reviews
13 repeat clients
9 years of experience
Eau Claire, WI, 54703

Aaralyn helped me out on super short notice and did a great job with my Luna!

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William K.
Sitter Profile Image: Mariah S.
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Mariah S.
from
$30
per night
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Lake Hallie, WI, 54729

Took great care of our doggo!

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Hanna O.
Sitter Profile Image: Alison L.
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Alison L.
from
$27
per night
5.0 out of 5 stars
8 reviews
1 repeat client
25 years of experience
Chippewa Falls, WI, 54729

About: I’ve taken care of dogs since childhood. I personally have had large dogs and small dogs so I have experience with all sizes. I very much enjoy walking dogs, so if this is something you need, I offer this service as well. I currently work as a full time teacher. I’m available 6-7:00 to check in your dogs, feed and water and then at 4 pm til 9 in the evenings. Depending on how far you are from my job I can possibly pop in during the day to check in your dog. Your pet is welcome in my home and will be part of my animal family, they are welcome on the couch and they’ll have lots of place to run on my 17 acres place. As long as your dog is house trained they will have the main level to hang out with my dogs while I’m at work. The weekends I’ll around all day and if I’m out and about and the weather is not hot they can come in my car for rides.

Sitter Profile Image: Katlin K.
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Katlin K.
from
$40
per night
4 years of experience
Bloomer, WI, 54724

About: I've had many dogs of my own so I'm quite personal & I'm always excited to make new animal friends. Having many animals of my own I think sets me aside from others, I love to play and run around with dogs. I also can and will care for other pets or animals if it is necessary, which I also think sets me apart. I'm an athlete too so long walks & everything are not a problem, I enjoy walking and nature so going on walks would be wonderful. I like animal of all sizes. Also by having pets of my own, I understand a lot about dogs and how to care for multiple. I can do more than just play & walk them, I can bathe them & brush & most other hygiene needs.

Sitter Profile Image: Jason K.
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Jason K.
from
$100
per night
10 years of experience
Chippewa Falls, WI, 54729

About: - Current Kennel Assistant (dogs and cats) in spare time - Dog Walking - Boarding - Playing - Ten plus years of experience - Walking area - Supplies available - Near vet - Close to Eau Claire My schedule is very flexible, so I can work as needed to help fit your schedule and the needs of your animals. Please let me know how I can help! Dependent on the service, I will make sure your animal is safe, fed, and having fun. Please ask any questions related to my current services

Sitter Profile Image: Nikki H.
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Nikki H.
from
$20
per night
16 years of experience
Eau Claire, WI, 54701

About: I’ve been taking care of pets since I was about 8 years old with my own labs! This extended into caring for family, family friends and eventually neighbors and the occasional stranger’s dogs as I got older. Care has included walking, feeding, administering oral medication, bathing, and plenty of play and cuddle time. I’ve even worked in a doggy daycare previously! I’m comfortable around dogs of all sizes, ages, and breeds. I am a current Master’s student commuting to UW-Stout Tuesdays-Thursdays, and work part time at a childcare facility on Mondays and Fridays. I would be available for a variety of afternoon or evening walks, potty breaks, or mealtimes! I would also be available on weekends for more in-depth care, stays and adventures. I live in an apartment that allows dogs, and am close to a variety of outdoor walking trails. Play time and cuddles are a free for all, but I tend to have specific areas for eating and sleeping for my dog. I am however comfortable with dogs on furniture, crating, or anything in between!

Sitter Profile Image: Olivia S.
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Olivia S.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
9 years of experience
Eleva, WI, 54738

Olivia did a great job watching our 2 pups and provided updates and pictures each day.

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Robert W.
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The median cost per night for house sitting in Drywood is $40

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Meet local sitters who will treat your pets like family

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Sitters in Drywood average 4
repeat house sitting clients

FAQs for House Sitting - Drywood

Frequently asked questions about Rover

The average cost for House Sitting in Drywood on Rover is $31.08 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 119 sitters on Rover offering House Sitting across Drywood. 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 Drywood 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 Drywood 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 Drywood 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.

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