House Sitting Chenequa

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Chenequa, 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: Kendra M.
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Kendra M.
from
$50
per night
5.0 out of 5 stars
• 13 reviews
2 repeat clients
3 years of experience
Oconomowoc, WI, 53066

“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: Tara R.
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Tara R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 85 reviews
20 repeat clients
20 years of experience
Delafield, WI, 53018

“Tara is amazing! Tara stayed with our two puppies for 4 nights at our house. Tara is so kind and a great communicator. We got lots of pictures and updates. The puppies were so happy and well taken care of. Our dogs were for sure disappointed when their time with Tara ended.”

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Olga L.
Sitter Profile Image: Faith B.
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Faith B.
from
$35
per night
4.9 out of 5 stars
• 11 reviews
4 repeat clients
10 years of experience
Hartland, WI, 53029

“Faith was amazing!! She was taking care of my 10 yr dog with special needs and loved her while I was on a week long business trip. She treated her with kindness and love!! Thank you Faith!!! I highly recommend her for any pet sitting needs you have!”

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Peg H.
Sitter Profile Image: vtheine@gmail.com T.
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vtheine@gmail.com T.
from
$42
per night
5.0 out of 5 stars
• 33 reviews
9 repeat clients
50 years of experience
Oconomowoc, WI, 53066

“Vonnie is a blessing to us. Our girl has separation anxiety but she loves Vonnie. It allows us to be able to get away without worrying about Rosy being anxious and miserable”

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Heidi H.
Sitter Profile Image: Meagan W.
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Meagan W.
from
$40
per night
5.0 out of 5 stars
• 23 reviews
7 repeat clients
19 years of experience
Pewaukee, WI, 53072

“Meagan has been with my dog Brody for most of June and July at my house p, very dependable and great with Brody. I highly recommend her for dog and house sitting”

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J C.
Sitter Profile Image: Taylor S.
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Taylor S.
from
$50
per night
5.0 out of 5 stars
• 10 reviews
5 repeat clients
25 years of experience
Delafield, WI, 53018

“My experience in working with Taylor was excellent. Great communicator and most importantly cared for my 10yr lab while out in a work trip. Taylor went above and beyond what was required as she left the house spotless, and washed bedding and bathroom towels before leaving.”

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Todd L.
Sitter Profile Image: Cooper B.
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Cooper B.
from
$70
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Hartland, WI, 53029

“Cooper is a kind, reliable pet sitter. I felt completely comfortable having him spend time with my dogs and stay in my home. I’d definitely work with him again and would encourage you to consider him for your needs as well.”

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Ryan P.
Sitter Profile Image: Alex M.
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Alex M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 49 reviews
16 repeat clients
10 years of experience
Oconomowoc, WI, 53066

“Loved Alex so much! I have an anxious little lady and the minute Alex walked in Soph laid on the floor and wanted tummy rubs. She had a very calming presence which was so comforting knowing she would be in good hands. She was so easy to communicate with and kept us updated while we were gone. Would love to use her again ❤️”

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Maria B.
Sitter Profile Image: Katelyn W.
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Katelyn W.
Star Sitter
from
$75
per night
4.8 out of 5 stars
• 36 reviews
16 repeat clients
8 years of experience
Oconomowoc, WI, 53066

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

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Danielle R.
Sitter Profile Image: Mary D.
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Mary D.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 9 reviews
2 repeat clients
15 years of experience
Delafield, WI, 53018

About: Loving, Reliable Pet Care Right In Your Backyard! Hi - I am a part-time local pet sitter who truly understands that pets are family. I am here to ensure your pets feel safe, comfortable, and cared for while you're away. I offer drop-in visits, dog walks, overnight (at your house) sitting, and can care for dogs, cats, and some birds. My goal is simple: keep your pet's routine as normal and stress-free as possible and to give you peace of mind. When you book with me, you can expect: -Plenty of love and attention (belly rubs included!) -Photo updates -Recap notes on how they did -I can administer oral meds if needed -Clean food and water bowls, tity litter boxes, and refreshed spaces I will always schedule a meet-and-greet first so I can learn about you, your pet's personality and preferences, and complete a profile for my records. I take reliability seriously and treat your home with the same respect I would my own. I look forward to meeting you and your furry (or feathered!) family members! I currently work full-time, and pet care is my part-time passion. My weekday availability (Monday–Friday) is limited to 5:00–6:00 AM and after 5:00 PM. I do have some flexibility depending on your needs and am happy to discuss specific timing upon request. Weekends are generally open unless otherwise marked unavailable on my calendar. Please feel free to reach out to discuss your pet’s needs—I’ll always do my best to accommodate when possible! At this time, I do not have the means to board pets at my house for an extended stay but am looking into it in the future.

Sitter Profile Image: Cindy S.
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Cindy S.
from
$55
per night
5.0 out of 5 stars
• 52 reviews
15 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: Kirstin B.
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Kirstin B.
from
$75
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
20 years of experience
Hartland, WI, 53029

“Kirstin watched our dog on short notice after another sitter had to cancel. She was so great! Our dog was recovering from being sick and Kirstin kept us updated and our dog taken care of. Piper enjoyed herself all weekend and Kirstin took great care of the house as well. We won’t hesitate to have Kirstin sit for us again in the future!”

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Shelby S.
Sitter Profile Image: Jade B.
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Jade B.
from
$60
per night
5.0 out of 5 stars
• 5 reviews
10 years of experience
Oconomowoc, WI, 53066

“Jade did a wonderful job sitting for Angel thru the 6 days when we were gone. I felt Angel was in good hands, she was very caring toward Angel. I could see Angel was very comfortable with Jade from the pictures Jade sent to me when I was traveling. Jade sent me daily pictures of Angel along with videos. That I really appreciated. I would recommend Jade to anyone who is looking for a good dog sitter. Kirsten M.”

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Kirsten M.
Sitter Profile Image: Tami G.
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Tami G.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 84 reviews
18 repeat clients
4 years of experience
Mukwonago, WI, 53149

“Tami was very concerned that my dog Oliver was taken care of well. Tami did a great job communicating with me with any questions and concerns. I would use her again as my dog sitter.”

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Tom R.
Sitter Profile Image: Tia R.
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Tia R.
from
$40
per night
20 years of experience
Delafield, WI, 53018

About: I have had pets my whole life. Currently I have 3 cats, 3 dogs, a hamster, and fish. I have also had bunnies, hermit crabs, and many reptiles. There is not an animal I don't love caring for or being around. I am good with animals of all ages and sizes!! I currently am a homemaker with an open schedule. I am available morning til night and overnights if needed. I have lots of time to spend with your pets! I care for every pet like they’re part of the family. I follow their normal routines for feeding, walks, playtime, medications, and rest, while giving them plenty of love and attention. I keep their environment clean and safe, and I make sure they get the exercise, enrichment, and companionship they need to feel comfortable and happy while you’re away.

Sitter Profile Image: Allison S.
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Allison S.
Star Sitter
from
$110
per night
5.0 out of 5 stars
• 56 reviews
21 repeat clients
3 years of experience
Sussex, WI, 53089

“Allison took wonderful care of our fur babies (and our home). We appreciated the frequent pictures/videos, since we missed our boys something terribly. Our cats are usually scaredy cats, and hide from strangers. Allison bonded with them quickly and they were comfortable with her around. One of our cats require daily medication, and Allison was such a pro, making sure he was well cared for. We truly appreciate her care and support of our family and home. Would highly recommend.”

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Thomas D.
Sitter Profile Image: Joey C.
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Joey C.
from
$65
per night
5.0 out of 5 stars
• 79 reviews
18 repeat clients
40 years of experience
Hartland, WI, 53029

“Joey continues to be the BEST dog sitter for our pups! She loves them and takes amazing care of them with daily updates and pictures. Joey leaves our house clean…probably cleaner than I leave it for her 😁 I recommend her 100%”

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Erin R.
Sitter Profile Image: Sara V.
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Sara V.
from
$45
per night
5.0 out of 5 stars
• 23 reviews
9 repeat clients
17 years of experience
Sussex, WI, 53089

“Sara recently stayed the night with my two dogs. My night away was made more relaxing, knowing that they were in great hands. Sara is conscientious, great with dogs, and a wonderful person.”

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Sue B.
Sitter Profile Image: Kimberly F.
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Kimberly F.
from
$40
per night
4.8 out of 5 stars
• 23 reviews
4 repeat clients
18 years of experience
Waukesha, WI, 53188

“Kimberly was fantastic in every way! She was so caring of Sunny who became quite ill while under her care. She handled everything professionally and compassionately. She went over and above, even accompanying our son to the vet.”

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Janice S.
Sitter Profile Image: Molly M.
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Molly M.
from
$75
per night
5.0 out of 5 stars
• 16 reviews
5 repeat clients
18 years of experience
Oconomowoc, WI, 53066

About: I grew up with dogs and have taken care of friends and families pets my whole adult life. I also have a dog of my own! I’m comfortable with dogs of all sizes and breeds and am reliable and comfortable walking, feeding, and providing all general cares! I work full time, day time hours, but mostly from home. I take care of my own pup during the day, we go on walks during my breaks and lunch. I’m available to walk or watch pets during the day, in the evenings/nights or on weekends! I have a golden retriever at home to keep your pet company ! He loves friends and making new ones! Close by walking paths and fields to walk, as well as a dog park on site if wanted.

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

Pet parents share their Rover experiences - Chenequa

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5.0 out of 5 stars

Taylor was great. She stayed with our cats over the holiday weekend. She was communicative and reliable!

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Jill S.
House Sitting
5.0 out of 5 stars

Taylor is amazing. Took great care of our recovering pooch and of our house. Will absolutely book her again.

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Mike O.
House Sitting
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Book with peace of mind

  • 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.

Meet local sitters who will treat your pets like family

  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
  3. 3. Book & Pay

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

Popular requests for house sitting - Chenequa

Select a filter and find qualifying sitters offering house sitting.

Sitters in Chenequa average 4
repeat house sitting clients

FAQs for House Sitting - Chenequa

Frequently asked questions about Rover

As of October 2026, there are 1,220 sitters on Rover offering House Sitting across Chenequa. 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 Chenequa 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 Chenequa 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.

<b>Tip:</b> 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 Chenequa 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 Chenequa. On Rover:

  • 92% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 98% 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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