House Sitting Lake Windsor

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

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pet parents in Lake Windsor have booked house sitting

Lake Windsor, 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: Tina B.
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Tina B.
Star Sitter
from
$35
per night
4.9 out of 5 stars
• 86 reviews
23 repeat clients
38 years of experience
Windsor, WI, 53598

“We've had Tina and her son Skylar as sitters for many years and they always do such a good job. Our pets love them and they are always sure to give frequent updates.”

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Maximillian O.
Sitter Profile Image: Kendra B.
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Kendra B.
from
$45
per night
5.0 out of 5 stars
• 2 reviews
30 years of experience
Glendale, Madison, WI, 53716

“Kendra was fantastic! She is a great communicator with lots of updates and pictures. ♥️ She walked the dogs often and knew how to handle our dog that barks at others on a leash! Thank you for taking great care of the crew!”

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Heidi R.
Sitter Profile Image: Emma R.
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Emma R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
10 years of experience
Sun Prairie, WI, 53590

“Emma was extremely helpful and took great care of the house and our kitten. The pictures she sent were greatly appreciated. We felt very comfortable with our home in her care.”

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Gretchen M.
Sitter Profile Image: Brandi V.
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Brandi V.
from
$50
per night
8 years of experience
Windsor, WI, 53598

About: I’ve been dog sitting for a couple years now. I’ve had experience from little to big dogs. From a basenji, labrador, german shepherd, great pyrenees mix, a yorkie, and a few other breeds! Friends rely on me to exercise, feed, and give attention to their fur baby. 😊 I have plenty of time on the weekends! I’m currently available at any time Friday-Sunday to take care of your sweet pets! Can start at any point of the day or night! I take care of pets as if they were my own! 🥰 I care about their safety, what they eat, who comes around them, how much outside time they get. I promise to take care of them and give them all the attention. I want to be able to give them some love and snuggles while watching some tv. I make sure to stick to their food schedule and like to let them out every 2-4 hours. Daily exercise is important to me, I like to go on walks and can always use a walking buddy! 🐶

Sitter Profile Image: Emilee K.
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Emilee K.
from
$50
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
11 years of experience
Sun Prairie, WI, 53590

“Emilee was AMAZING while we were gone for the week! We have three rescue pups all with various needs and anxieties and Emilee could not have been more patient, kind, or accommodating for the three of them. She kept us regularly updated and even offered some guidance/ideas from her years of professional work with dogs. We hope she's available next time we're headed out of town - we can't imagine leaving them with anyone else!”

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Andrew S.
Sitter Profile Image: Allix C.
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Allix C.
from
$35
per night
5 years of experience
DeForest, WI, 53532

About: I have a 1.5 year old golden retriever that I have single-handedly raised. I grew up with family dogs, cats, and farm animals. I have a Bachelors of Science degree in Animal Science. I interact with dairy farmers for my full time career and get to bring my dog along with me! I am a full-time employee that is 50% remote and 50% on farms. I have more flexibility when working remotely to walk, feed, and check on your furry friends. I currently make sure my pup gets at least 2 walks a day. On the weekends, I can cater to whatever schedule you need. I understand inviting a stranger into your home and your dog’s safe space can be overwhelming. I want to mitigate that as much as possible by not being a complete stranger and build trust with you as the owner and with your pups. I will try my hardest to make sure your dog feels safe, cared for, and protected while under my care.

Sitter Profile Image: Samantha M.
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Samantha M.
Star Sitter
from
$62
per night
5.0 out of 5 stars
• 20 reviews
6 repeat clients
10 years of experience
Madison, WI, 53704

“I couldn’t be more grateful to Sam! Our pup can be so picky - but he settled in with her quickly and she got him to eat! Not an easy task. I loved the photos and updates-helped me feel so much better while being away. She also had great communication prior and during. Highly recommend Sam!”

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Debra B.
Sitter Profile Image: Lynne O.
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Lynne O.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 18 reviews
3 repeat clients
30 years of experience
Fitchburg, WI, 53711

“Lynne did a great job taking care of Jett for the day. He was happy and wild as usual when I got home. She was friendly and very attentive. I will use her again!”

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Amber R.
Sitter Profile Image: Tatyana K.
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Tatyana K.
Star Sitter
from
$55
per night
4.9 out of 5 stars
• 82 reviews
27 repeat clients
4 years of experience
Fitchburg, WI, 53713

“Absolutely wonderful experience! Our pups were happy and calm when we returned home from a long afternoon/evening away. Tatyana definitely understands how to handle large, rambunctious (and love and adorable) dogs. She sent me pics throughout the evening as well, which was so lovely to receive.”

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Tamara M.
Sitter Profile Image: Sam B.
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Sam B.
from
$30
per night
19 years of experience
Capitol, Madison, WI, 53703

About: I’ve been caring for animals since I was old enough to know what a pet was, whether it’s my own, a neighbor’s, or a friend/family member’s. I love animals, and am considering going into vet work! I have experience with both puppies/kittens and seniors as well :). I can walk, feed, give meds, and do anything you need! I’m a full-time student during the week, but I will always have time to drop-in, or stay overnight. I’m very flexible with my scheduling, so I will happily do whatever you and your pet need! While I can’t offer boarding at my home because I have four roommates, I will care for pets in every way possible no matter what! I know some nice parks for walks, and I’m also happy to chill if they’re a homebody! Again, entirely up to you and your pets needs :)

Sitter Profile Image: Ingrid L.
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Ingrid L.
from
$55
per night
5.0 out of 5 stars
• 8 reviews
3 repeat clients
10 years of experience
Marquette, Madison, WI, 53704

“Ingrid is the best! We'd trust her with our pup anytime.”

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Amara R.
Sitter Profile Image: Emily B.
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Emily B.
from
$75
per night
5.0 out of 5 stars
• 57 reviews
14 repeat clients
10 years of experience
Madison, WI, 53718

“Emily was excellent. She took great care of our senior boxer. She took him on walks, made sure he was let out and gave him extra loving care.”

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Kate F.
Sitter Profile Image: christopher W.
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christopher W.
from
$120
per night
5.0 out of 5 stars
• 10 reviews
45 years of experience
Madison, WI, 53705

About: I’ve taken care of animals since I was five years old. I’ve walked dogs since I was a child. I have had birds, gerbils, lizards, fish, cats, and dogs. My last animal companion was a rescued special needs Jindo dog from LA. I truly love all animals. I prefer to focus one on one interactions with animals to ensure the best possible care and connection. I work for myself so my schedule is relatively flexible. I am available anytime with enough headway. Have car and can travel to clients. I can spend as much or as little time as your animal companions require. I currently have no pets or housemates and a fenced in backyard for dogs. My house is safe and secure and situated in a quiet neighborhood. All furniture is pet friendly and accessible. Plenty of windows for cats to look out from.

Sitter Profile Image: Lenys H.
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Lenys H.
from
$75
per night
4.9 out of 5 stars
• 32 reviews
12 repeat clients
12 years of experience
Mayfair Park, Madison, WI, 53714

“Lenys did a fantastic job watching my dog Miles. She was very attentive to him, and she provided transparent communication as well as pictures throughout the week. I would highly recommend her.”

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Benjamin J.
Sitter Profile Image: Thais M.
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Thais M.
from
$30
per night
5.0 out of 5 stars
• 1 review
5 years of experience
Capitol, Madison, WI, 53703

“Thais was wonderful! It was a 13 day stay as we were out of the country. She kept us informed and sent pictures of our pets which helped me know they were being taken care of - highly recommend!”

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Tamie G.
Sitter Profile Image: Ansheera H.
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Ansheera H.
from
$55
per night
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
Rolling Meadows, Madison, WI, 53714

About: I’ve shared my life with animals for over a decade, and my heart truly belongs to dogs and cats. As a homeowner and a "dad" to three pets of my own, I understand that your animals aren't just pets—they’re family. Why Choose Me? -I’ve been with my own buddies for 10 years, navigating everything from post-op surgery care and complex medication schedules to senior "attitudes" and puppy smiles. -I am a hybrid worker with a flexible schedule and my own transportation, making it easy for me to drop in for walks or midday snuggles. - I treat every home with the same care I give my own. You can expect a clean space and frequent, proactive communication so you never have to wonder how things are going. -Whether your pet has a specific routine or a quirky habit, I follow instructions to the letter to ensure their comfort remains consistent. I know the peace of mind that comes with knowing your fur babies are happy, safe, and loved while you’re away. I’m here to provide that same comfort for you. Work mostly from home with one day in the office. Very flexible on needs and schedule! Up early and go to bed late, which makes my schedule open to accommodate the needs of our little fur friends. I respect your space, privacy, and needs to ensure your home is just the way you left it when you return. In my home, we keep a clean ship, organized, and make sure all fir buddies are rewarded with treats when good behaviors are exhibited. With instruction, can be mindful of any special needs for our fur friends. Their health and comfort matters too!

Sitter Profile Image: Caroline S.
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Caroline S.
from
$34
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
15 years of experience
Tenney-Lapham, Madison, WI, 53703

About: I’ve taken care of dogs since I was in middle school, often dog sitting for neighbors and friends! I grew up with dogs and now have a sweet 2 year old terrier of my own I'm currently working full time so I am looking for more weekend and holiday gigs! This being said I work downtown and usually get off right at 5, so can do evening walks. I have a friendly 20 lbs terrier of my own who loves to play play play! Your pup will certainly not be bored if staying at my home.

Sitter Profile Image: Paige J.
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Paige J.
from
$65
per night
5.0 out of 5 stars
• 11 reviews
1 repeat client
3 years of experience
Madison, WI, 53718

“Paige was incredible. She offered to come by to meet my dog and get a lay of the land prior to my booking and sent me lovely pics and updates all weekend. Highly recommend her!”

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Angela T.
Sitter Profile Image: Lauren C.
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Lauren C.
from
$50
per night
20 years of experience
Emerson East, Madison, WI, 53704

About: I grew up with 3 cats and a golden retriever, and I've been caring for neighbors' and friends' cats for years — playtime, cuddles, and lots of patience for shy kitties. I volunteer at Shelter from the Storm, where I foster and care for cats in need. Whether your cat is super playful, a total lap cat, or a bit shy, I'll make sure they feel safe, loved, and right at home with me. I also love dogs and have 20 years of pet care experience. I host dogs over 1 year old, one pet at a time, so your dog gets all my attention. I work full-time but have good flexibility in the mornings, evenings, and weekends. This means I can easily do drop-in visits, walks, and overnight boarding on weekends. I’m usually available early mornings before work and evenings after work to care for your pets! I have a big yard where pets can safely play and explore. Your pet will get constant supervision, lots of playtime, and a calm, loving home environment. I can crate your dog if needed and will always follow your specific instructions.

Sitter Profile Image: Sarah W.
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Sarah W.
from
$45
per night
5.0 out of 5 stars
• 12 reviews
1 repeat client
12 years of experience
Madison, WI, 53713

“Sarah was so great with Hamm and made sure he received all the attention he needed! It was our first time leaving for the weekend since we got Hamm, and it was a comfort knowing Hamm was well taken care of while we were gone. She made sure to send all the cute pics of Hamm and was great to communicate with. Will definitely be booking with her again!!”

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Catherine & Zach S.
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The median cost per night for house sitting in Lake Windsor is $50

Pet parents share their Rover experiences - Lake Windsor

1 / 1
5.0 out of 5 stars

Thank you for taking care of Nova and Angel! Tina did wonderful job! I am definitely going to rebook her in future if she is available :)

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Alka C.
House Sitting
5.0 out of 5 stars

Lensy did a great job pet sitting at our house for three nights. She sent a lot of pictures that showed that Reggie was having a good time. We came home to a happy cat and our house was just as we had left it. We greatly appreciated her services!

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Kathleen K.
House Sitting
5.0 out of 5 stars

This was our first time using Rover, and Emilee made the entire experience so easy and reassuring. She was incredibly responsive, patiently answered all of our questions, and even proactively reached out with questions of her own to make sure she understood Harper’s routine and needs. Communication throughout Harper’s overnight stay was top-notch, and we felt very comfortable knowing she was in good hands. We had a great first experience and would absolutely recommend Emilee and use her again!

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Carolyn L.
House Sitting
5.0 out of 5 stars

Rebecca did a great job caring for our pets in our home! We received lots of photos and updates. She cleaned up a couple of pet messes too!

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Kate H.
House Sitting
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  • 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

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  • Reservation protection

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

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

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for house sitting - Lake Windsor

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Sitters in Lake Windsor average 4
repeat house sitting clients

FAQs for House Sitting - Lake Windsor

Frequently asked questions about Rover

The average cost of House Sitting in Lake Windsor is $39 per night as of November 2026. Most bookings cost between $39 and $39 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 796 sitters on Rover offering House Sitting across Lake Windsor. 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 Lake Windsor 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 Lake Windsor 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 Lake Windsor 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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

  • 92% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 95% 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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