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

Tara was fabulous - Hutch was very spoiled with multiple daily walks and I got lots of pictures and updates. He barely acted like we’d been gone!

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Lisa W.
Sitter Profile Image: Kendra M.
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Kendra M.
from
$45
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: Meagan W.
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Meagan W.
from
$40
per night
5.0 out of 5 stars
20 reviews
6 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: 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

Murphy Loved Vonnie! And she sent pictures. She's amazing! I will definitely be reaching out to her again. Best Sitter Ever. Totally made me feel comfortable leaving my best buddy with her. She is AWESOME!

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Patrick P.
Sitter Profile Image: Katelyn W.
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Katelyn W.
Star Sitter
from
$60
per night
4.8 out of 5 stars
34 reviews
16 repeat clients
8 years of experience
Oconomowoc, WI, 53066

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

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James F.
Sitter Profile Image: Faith B.
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Faith B.
from
$35
per night
4.9 out of 5 stars
10 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: Catilyn Z.
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Catilyn Z.
Star Sitter
from
$75
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
8 years of experience
Waukesha, WI, 53186

Catilyn was amazing! She watched our dog Roxy for a long weekend and took amazing care of her! She sent regular updates and pictures, made sure Roxy was let out often, and spent a lot of time with her. We would love to have Catilyn stay with Roxy again in the future!

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Emma L.
Sitter Profile Image: Allison S.
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Allison S.
Star Sitter
from
$88
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: Tami G.
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Tami G.
Star Sitter
from
$55
per night
5.0 out of 5 stars
78 reviews
15 repeat clients
4 years of experience
Mukwonago, WI, 53149

Tami did a great job taking care of my dog and cats. She sent lots of pictures and responded quickly when I needed to schedule a sitter on short notice.

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Terri D.
Sitter Profile Image: Stephanie S.
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Stephanie S.
from
$50
per night
4.9 out of 5 stars
64 reviews
25 repeat clients
28 years of experience
Mukwonago, WI, 53149

Had a great house sitting visit with Stephanie yet again and plan to utilize her services in the end of June as well. She and Jimmy had a great week while I was out of town. She sent pictures and kept me updated on how things were going. She didn’t just just sit with Jimmy, she actively played with him. I could tell in the pictures Jimmy was having a great time! Also - during my week away, Jimmy found new born bunnies in my fenced in back yard (that’s a first for me) and Stephanie went above and beyond with not only noticing that and updating me, but also making sure Jimmy let them have their space. Highly recommend, Stephanie!

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Jenna Z.
Sitter Profile Image: Marinda M.
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Marinda M.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
6 years of experience
Waukesha, WI, 53188

The dogs loved her! She made them feel comfortable enough to wrestle and continue their normal day to day activities. Will definitely be using in the future.

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Paige B.
Sitter Profile Image: Allie G.
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Allie G.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Waukesha, WI, 53188

The best experience ever. My precious pup just instantly loved her. She played with him and loved on him. She was prompt and just a very kind person. She even brought him special treats! I will use her again!

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Carolyn H.
Sitter Profile Image: Taylor S.
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Taylor S.
from
$50
per night
5.0 out of 5 stars
10 reviews
4 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: Amber K.
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Amber K.
Star Sitter
from
$40
per night
4.8 out of 5 stars
12 reviews
6 repeat clients
10 years of experience
Waukesha, WI, 53186

Amber is amazing, she came over and our dogs took to her immediately. Our oldest puppy can be a little challenging due to her being skittish, but Amber’s personality and energy helped ease her nervousness. Very reliable, and was able to help us out on short notice. I HIGHLY recommend!

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Shenlee S.
Sitter Profile Image: Cooper B.
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Cooper B.
from
$70
per night
5.0 out of 5 stars
7 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: Emma B.
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Emma B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
24 reviews
7 repeat clients
20 years of experience
Cedarburg, WI, 53012

Emma is amazing! I loved that she wanted to meet me and Lacey before she accepted a job. It was important to her that we were all on the same page. I was able to talk about Laceys needs and routine in person, which really made me feel at ease. When the weekend came for her to stay at our house I was completely comfortable leaving Lacey in her care. She gave me updates and pictures which was great. Thank you Emma!!!!

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Paula R.
Sitter Profile Image: Aimee R.
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Aimee R.
from
$35
per night
5.0 out of 5 stars
8 reviews
1 repeat client
20 years of experience
Waukesha, WI, 53186

Aimee was great. She made sure the pups were loved the entire time and these two bulldogs want to be with people. Aimee kept the pups happy the entire time. Aimee communicated great and was very responsive if I checked in on things myself. I definitely recommend Aimee...as long as it isn't during a time where I would love her to stay with my pups, lol.

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Doug H.
Sitter Profile Image: Brandi W.
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Brandi W.
from
$35
per night
5.0 out of 5 stars
21 reviews
6 repeat clients
8 years of experience
Mukwonago, WI, 53149

Brandi is outstanding, I highly recommend! She is always sweet and kind to both our adorable furry family members. Our two dogs are medium sized and one is extremely shy. Brandi is patient and always wins them both over with her special touch and love. Did I also mention how reliable she is? I am always grateful knowing she is at home with our dogs while traveling.

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Shenlee S.
Sitter Profile Image: Bella B.
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Bella B.
from
$63
per night
5.0 out of 5 stars
35 reviews
18 repeat clients
15 years of experience
Watertown, WI, 53094

It was so nice to have Bella cat/house sit for us on our recent trip. So comforting to know our cats had a person to spend time with in the evenings and give them lots of attention. She also left our place super clean! Would definitely ask back. Thanks Bella!

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Kelly S.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$85
per night
5.0 out of 5 stars
54 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

Ramsey did an excellent job taking care of my two labs. I enjoyed regular pictures and updates on what they were doing. They were obviously loved; and very happy campers upon my return from a short trip. I felt confident in having Ramsey stay in my home, and really glad the dogs could keep their regular routine.

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

Pet parents share their Rover experiences - Chenequa

1 / 1
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 September 2026, there are 1,210 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.

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

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

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

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

Yes, you can find sitters who have experience with handling special pet needs in 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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