House Sitting in Wyndemere, Madison, WI

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Andrew L.
1.
COVID SAFE 24/7 online Vet accessGreenbush, Madison, WI, 53715
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

“Uncle” Drew loved our girl while we were away. She went on walks, car rides, puppy play dates, cuddled on couches and got treats. Drew sent us pictures every d… (more)

from
$80
per night
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Camille M.
Outgoing, student, dog loverMiddleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

Camille did an amazing job watching our older dog who is finicky and very particular about food, walks, and sleep while we were gone overnight for a few days. S… (more)

from
$35
per night
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Ruthanne F.
I pawsitively love dogs and cats!Old Middleton Greenway, Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Ruthanne was great! She stayed at our house for a over a week, all three of our dogs enjoyed her! We have a senior dog with medications/allergies and other care… (more)

from
$45
per night
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Cheyenne K.
Expert and Loving Animal CaretakerBurr Oaks, Madison, WI, 53713
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Cheyenne is THE BEST! We have had her do drop ins for us before that went great and recently had her stay with our 2 fur babies for 3 nights and she was amazin… (more)

from
$80
per night
Kate K.
5.
Cared for as if you were homeMiddleton, WI, 53562
House Sitting, Drop-In Visits

This was our first time having Kate - she did a great job with our dog who is quite shy with new people! She got her to take her meds and made sure she was fed … (more)

from
$45
per night
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6.
Energetic lover 🥰 of Fur-babies!Middleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

Donna was great with the pups and we would definitely pick her again to watch them. She came to meet them a few days before and stayed at the house overnight. W… (more)

from
$45
per night
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7.
Home is where the bark isFitchburg, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Robert was very friendly and easygoing. My puppy absolutely loved him, they were inseparable at the end of the day. I will definitely be reaching out to Robert … (more)

from
$28
per night
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8.
New grad animal-loverVilas, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Kelsey was great with our puppy Riley!!. It was our first time leaving him with someone he didn’t know and he was very comfortable with her. We will definitel… (more)

from
$50
per night
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9.
Your dog's new bestie!Madison, WI, 53717
House Sitting, Drop-In Visits, Dog Walking

Sara was fantastic with our last minute request. We felt not only comfortable, but that the dogs would be having a fun time with Sara there! Great pictures an… (more)

from
$50
per night
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10.
Animal loverRegent, Madison, WI, 53726
House Sitting, Drop-In Visits, Dog Walking

Cybill has been amazing with my puppy Oakley! She sent updates and photos every day and is very responsible, flexible and reliable individual. You can really te… (more)

from
$45
per night
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11.
Trained 12+ dogs. Enjoy walksWesthaven Trails, Madison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking

Lucas came around often to hang out and exercise my girls. He was sending me updates and pictures all along so I knew how they were doing. My GSD puppy is a ha… (more)

from
$35
per night
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12.
The Best Care For Your Companion!Meadowood, Madison, WI, 53711
House Sitting, Drop-In Visits, Dog Walking

Carissa did a fantastic job again!! We had to leave our boy alone this time as his sister was feeling very sick and stayed with the vet. Carissa made sure Att… (more)

from
$50
per night
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13.
Incoming college freshman dog loverHigh Point Estates, Madison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Bella did a great job house sitting my dog! She kept him safe and happy the whole week were out of town. Thanks Bella! (more)

from
$45
per night
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14.
Fun, energetic dog sitter & boarderMadison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Emily took excellent care of our two dogs while we were away and we are looking forward to having her and her sweet dog Belle come house sit for us again! (more)

from
$35
per night
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15.
Daily visits to the dog park!Marbella, Madison wi, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Clara loves dogs and has been around them her entire life! She is a responsible pet owner herself to an adorable German Shepard. She enjoys walking, playing a… (more)

from
$75
per night
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16.
Liz 
Verified Enhanced Background Check
Current UW Veterinarian StudentMiddleton, WI, 53562
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Liz did a wonderful job taking care of my cats! She was an excellent communicator while I was gone, sending texts and photos daily. She handled the meds and sub… (more)

from
$50
per night
17.
Love walks and love dogs!Spring Harbor, Madison, WI, 53705
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I appreciate that Lauren was very attentive asked questions and texted me pictures I came home to find the dogs calm and tired so they obviously had a good walk… (more)

from
$50
per night
18.
Fun sitter with small service dogMiddleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

We're very happy with the job Kally did for us. She took great care of our dog, our cat, and our home. Will definitely call her next time! (more)

from
$25
per night
19.
Easygoing pet lover in grad schoolMadison, WI, 53711
House Sitting, Drop-In Visits

Once again we came home to healthy, happy kitties! We are so grateful for Bree’s care and understanding, since two of them have some special needs! (more)

from
$70
per night
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20.
Experienced petsitterMadison, WI, 53719
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Amanda was the manager of the daycare I take my Ziggy to, she is amazing. Always so friendly and greeted Ziggy like he was the only dog she had seen all day. Z… (more)

from
$60
per night

Pet parents in Wyndemere, Madison, WI love dog sitters on Rover.com. 423 owners have reviewed sitters in Madison, giving them an average rating of 4.9/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Wyndemere house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Wyndemere, Madison, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Wyndemere house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Wyndemere, Madison donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Madison.

We're proud to support over 200 organizations across the nation, including: