House Sitting Lake Windsor

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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
• 84 reviews
23 repeat clients
38 years of experience
Windsor, WI, 53598

“We have used Tina multiple times when we travel. She does a great job with taking care of our dog and our house and we are confident he is well cared for when we are gone.”

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Michele L.
Sitter Profile Image: Tiana B.
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Tiana B.
from
$50
per night
5.0 out of 5 stars
• 32 reviews
13 repeat clients
5 years of experience
DeForest, WI, 53532

“Tiana was amazing with our dog and the house was well cared for while gone for an extended period of time. She provided regular updates with pictures that were much appreciated when we started to miss our baby girl.”

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Sylvia L.
Sitter Profile Image: Holly & Ana Maria P.
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Holly & Ana Maria P.
from
$32
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
12 years of experience
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53704

“I would definitely recommend Holly and Ana Maria’s services! They took great care of my two anxious pups. I felt very at ease and knew my dogs were in good hands. I got lots of pictures of the pups having so much fun!”

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Avi I.
Sitter Profile Image: Camille M.
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Camille M.
from
$55
per night
4.9 out of 5 stars
• 55 reviews
25 repeat clients
15 years of experience
Tenney-Lapham, Madison, WI, 53713

“We absolutely love Camille! She handles our elderly dog, Leo, so well. She is an excellent communicator and we can tell that she really loves our dog.”

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

“Tatyana did a great job with our three dogs who range in size from a 90 lb German shepherd down to a 25 lb mutt. She sent pictures and videos, and with it being the first time she watched our dogs, it made me feel 100x more comfortable. We also had one dog who needed to take medication that she ensured was administered.”

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Paige S.
Sitter Profile Image: Samantha R.
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Samantha R.
Star Sitter
from
$65
per night
4.9 out of 5 stars
• 139 reviews
48 repeat clients
18 years of experience
Reston Heights, Madison, WI, 53718

“Samantha was very communicative and attentive to my pets’ needs. I returned from vacation to happy dogs and a clean home. I would definitely work with Samantha again!”

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Kelly C.
Sitter Profile Image: Louisa S.
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Louisa S.
from
$70
per night
5.0 out of 5 stars
• 9 reviews
3 repeat clients
15 years of experience
Heistand, Madison, WI, 53714

“Louisa was excellent! She was so thorough in our meet and greet making sure she was aware of any and all needs Ollie might have. Ollie loved her right away which made me feel very comfortable. Louisa was great at communicating and sent pictures during the sit which I appreciated. Highly recommend her and will certainly have her care for Ollie in the future!”

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Angi K.
Sitter Profile Image: Stacy S.
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Stacy S.
from
$75
per night
5.0 out of 5 stars
• 17 reviews
6 repeat clients
45 years of experience
Madison, WI, 53704

About: I have lifelong experience with a multitude of animals. From dogs, cats and ferrets to rodents, fish and reptiles. I am a lover of all animals. I have a soft spot in my heart for bully breeds. I have experience with seniors, as well. I have a relatively flexible schedule. I have availability early morning thru evenings, weekdays and weekends. I have my own business, so I can set my own hours. I am available to take care of your pets in your home. I am willing to take care of any and all pets, not just cats and dogs. I can also water your plants, if needed. I will administer medications, walk, pet, bathe, play with, enrich, etc. all of your pets!

Sitter Profile Image: Brienna T.
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Brienna T.
from
$55
per night
4.8 out of 5 stars
• 5 reviews
10 years of experience
Madison, WI, 53704

About: Hi! I’m a reliable, caring dog lover who treats every pup like my own. Whether it’s walks, playtime, or cuddle time, I’ll make sure your dog feels safe, happy, and loved while you’re away. I’ll follow your pet’s routine and keep you updated so you can have peace of mind! I'm a part-time student who takes morning classes Monday-Thursday. I am typically at home the majority of the day, but if I am ever away I will return home for about an hour to take any guests out during lunch (12-1PM). Weekends, I am mostly free. Drop-off/pick-up can be anytime! My schedule is pretty flexible during weekends so if you need a specific time, I can make it work. I'm very accommodating. Just let me know in advance when you are thinking about booking and I can check my schedule for that day. If you have a busy schedule, I can also pick-up and drop-off for free! Let me know what your fur-baby's routine is like (sleep, eat, play schedule). I hope to make your fur-baby comfortable while you are away. For DROP-INS: I have experience with drop-ins for dogs, cats, and fish! If you would like me to do a short walk during the 30 minute drop-in for your pup, let me know! I typically like to refresh their water, give a treat (if you allow it), and make sure they go potty! For cats, I will make sure their water & food is replenished and will clear out litter boxes! I will also water your plants, bring in your mail/newspapers (if requested). Thanks for considering me! Let’s set up a Meet & Greet! **Holiday Rates will also be applied for Easter, Mother’s Day, and Father’s Day weeks/weekends** I’m currently working part time with plenty of time for fuzzy friends! I haven’t found my perfect pet just yet, so I have lots of love to give! I have loads of experience training young and old pups, no matter the service your looking for I would love to incorporate good habits for your pet!

Sitter Profile Image: Jen C.
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Jen C.
from
$55
per night
5.0 out of 5 stars
• 17 reviews
5 repeat clients
10 years of experience
Eastmorland, Madison, WI, 53714

“I can’t say enough good things about Jen! She is so incredibly communicative, conscientious, and kind in all our interactions. She treated our dog Melvin with so much care and gave a lovely report at the end of each day to let us know how things went (including adorable photos). Jen also went above and beyond to clean up our place before she left. She’s fantastic!”

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April S.
Sitter Profile Image: Karina M.
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Karina M.
from
$45
per night
5.0 out of 5 stars
• 26 reviews
6 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

“Karina always shows such care for my pets. My dog and cat both have health issues that require multiple medicines and supplements. She always follows their routine closely, asks questions to make sure she’s providing good care, takes my dog on daily walks, and sends daily pictures. I also come home to a clean house. I will not hesitate to request pet/house sitting from Karina again and I highly recommend her!”

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Hailey L.
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: Ansheera H.
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Ansheera H.
from
$55
per night
5.0 out of 5 stars
• 1 review
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: Jamie Z.
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Jamie Z.
from
$55
per night
5.0 out of 5 stars
• 5 reviews
2 repeat clients
2 years of experience
Waunakee, WI, 53597

About: I’ve grown up with dogs my entire life and currently have three dogs of my own, all with very different personalities and needs. I’ve put a lot of time into training and creating a successful multidog household, which has given me experience with everything from basic obedience and leash manners to reactivity, resource guarding and special-needs dogs. I’m comfortable following established routines, using the training methods and equipment your dog is accustomed to, and adjusting my approach based on each individual dog. I understand that not every dog is a social butterfly, and I’m happy to give dogs the space, patience and structure they need to feel comfortable. Most importantly, I know how nerve-wracking it can be to trust someone else with your dog. I’ll care for yours with the same attention and respect I expect for my own. As a registered nurse, I’m dependable, detail-oriented and comfortable following specific care and medication instructions. I am not only certified in human CPR but also Red Cross Dog/Cat/Pet CPR and first aide certified. I’m also used to communicating clearly, so you can expect plenty of updates while your dog is in my care I’m an RN with a rotating schedule, which gives me several days off during the week and plenty of flexibility to care for your pets. On my days off, I’m available for walks, drop-in visits, playtime and plenty of attention! I am home most of the time and my husband works from home so someone will usually be here. With the occasional instances of going out a few hours at a time. We do keep our dogs crated while we are gone and have cameras on the kennel/dog room to keep an eye on them. I know every dog has their own routine, personality and comfort level. I’m happy to follow your established routine and any specific instructions for feeding, walks, medications, crates or training. I have experience with multidog households, reactive dogs and special-needs dogs, so I’m comfortable adjusting my approach to what makes your dog feel safest and most comfortable. I’ll also keep you updated with photos and messages so you can feel confident your pet is well cared for while you’re away

Sitter Profile Image: Talia W.
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Talia W.
from
$28
per night
4.9 out of 5 stars
• 10 reviews
3 repeat clients
11 years of experience
McFarland, WI, 53558

“Very communicative and well organized. Our dogs loved her. Talia is trustworthy and left our house nicely when we got home. We will be booking again!”

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Rj R.
Sitter Profile Image: Maricel E.
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Maricel E.
from
$55
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
10 years of experience
Heistand, Madison, WI, 53714

“Maricel was great with Oreo and kept me uptodate with walks and activities. She took great care of Oreo and he was a happy dog when I got home!!!”

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John T.
Sitter Profile Image: Kylie E.
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Kylie E.
from
$65
per night
5.0 out of 5 stars
• 12 reviews
6 repeat clients
20 years of experience
Stoughton, WI, 53589

“Kylie was great with Deuce! She sent several pics while I was away, which was great. She even stayed later, after I had delayed service at dinner. Great service.”

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Alicia C.
Sitter Profile Image: Halle C.
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Halle C.
from
$30
per night
15 years of experience
Madison, WI, 53704

About: Hi, I am Halle! I grew up with many dogs, including a Pug, Pomeranian, Wheaton Terrier, Golden Doodles, a Poodle, and Boston Terriers. I worked at a dog groomers and have experience pet sitting other breeds, including Labs, Alaskan Klee Kai, Great Pyrenees, Border Collies, and other mixed breeds. Because of this background, I am very comfortable with high energy puppies, large breeds, and senior dogs that need a slower pace on walks. If you choose to board your dog at my apartment, my routines include 30 minute walks, play time in a fenced in dog park (which is apart of my complex), feeding, and baths as needed. I am comfortable giving them medication as long as there are instructions (for example, oral medicine with instructions provided by a veterinarian). I highly prefer that your dog is potty trained and does not bark loudly, as I will not be at my apartment the entire time to watch them. Safety is my number one priority for myself, the dogs, and their caregivers, so proper communication will be required for Rover services. I’m currently available for walks in the morning and afternoons. If you board your dog at my apartment, I will take them on 3-4 walks per day. I am flexible right now and my schedule can change depending on the services you request. Walks- I can come to your house/apartment to take your dog on a walk. Client’s home pet sitting service- same applies^- I can come to your house/apartment to care for your pet’s needs. Boarding in my home- I request that your pet be dropped off at my apartment with food and food/water bowls, toys, leashes, and their crates if they need them. I maintain a clean, safe apartment and do not have my own pets. My apartment complex has a large fenced in dog park. I will regularly take your dog to this park for play time during their boarding. *Safety- there is no smoking or other dangerous activities in my home. Communication is my priority to ensure that your pet remains safe and healthy. I will provide periodic updates to confirm that they have been fed, walked, played with, etc during your service.

Sitter Profile Image: Eric &  Rachel D.
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Eric & Rachel D.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 36 reviews
9 repeat clients
12 years of experience
Capitol, Madison, WI, 53703

“Eric and Rachel were absolutely amazing with our pups! In fact, we already rebooked them before this first booking was even done because we were so happy with how they were treating our pups and their great communication. We have older dogs and our oldest is 14 with some health issues. We haven’t used a pet sitter since our dogs were much younger. So we were very nervous going into this, but Eric and Rachel took amazing care of our dogs, we’re patient loving with them, and always sent us updates and pictures. They also took great care of our home while they were staying there. They and their dog Lilo all have experience with rescue dogs, and you can see that and how they were able to adapt to the quirks and needs of our older dogs. Would recommend without hesitation!”

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Spencer I.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$75
per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Madison, WI, 53704

“Great communicator and our girls love her. Thank you!”

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Karen M.
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Pet parents share their Rover experiences - Lake Windsor

1 / 1
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

Tina took great care of Cleo while we were away for an extended weekend. She sent lots of pictures and made sure Cleo felt comfortable during a storm that passed through. She also left the house near and tidy.

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Jayme B.
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?

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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

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FAQs for House Sitting - Lake Windsor

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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 , 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 .

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 .

sitters on Rover set their own , 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 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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