House Sitting Oakbridge

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

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Over 21
pet parents in Oakbridge have booked house sitting

Oakbridge, 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.

1 / 1
Sitter Profile Image: Tucker S.
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Tucker S.
Star Sitter
from
$48
per night
4.8 out of 5 stars
• 17 reviews
4 repeat clients
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

“Tucker was amazing — he took great care of my fur baby and provided pics regularly AND he was gracious and unflappable in the face of some unforeseen challenges. Flexible, great communicator, and left the house cleaner than he found it. Great with following directions and proactively taking care of all the things — he even noticed the light on the automatic feeder and refilled it before I even messaged him about the notification I’d received. Perhaps best of all, he saw AJ for the loving, playful kitty that he is—so I knew AJ was feeling comfortable and that he was in good, kind hands. Would definitely recommend to others and would be glad to have his help again!”

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Sarah G.
Sitter Profile Image: Anna H.
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Anna H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 37 reviews
10 repeat clients
7 years of experience
Middleton, WI, 53562

“Smooth meet-up & sitting experience, and great level of communication! She was reliable and trustworthy in taking care of our pups and the house. Would definitely work with you again and looking forward to it!”

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Hanna E.
Sitter Profile Image: Megan B.
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Megan B.
from
$65
per night
5.0 out of 5 stars
• 12 reviews
8 years of experience
Madison, WI, 53719

“Megan took excellent care of my pups while I was away. One of my dogs became ill right before I left. She kept me updated on his condition and her concerns, as well as handling my sassy girl! I will definitely use her services again! My pups loved her.”

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Leah H.
Sitter Profile Image: Lisa T.
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Lisa T.
Star Sitter
from
$102
per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
2 years of experience
Madison, WI, 53719

“Lisa did a terrific job with our fur babies! She was very careful and caring with them, kept us posted with the right amount of details, and kept the home really clean. Would definitely have her sit for us again!”

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James W.
Sitter Profile Image: Alyssa J.
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Alyssa J.
from
$28
per night
15 years of experience
Madison, WI, 53719

About: Growing up, my house has always had at least three dogs (both big and small), and I could never imagine my life without pets. I currently live with a dog (pitty mix) and a cat (a cuddly gray tuxedo)! I adopted my dog about a year ago through a rescue, so I’ve also had some very recent training refreshers! I have taken animal husbandry - including first-aid on dogs and cats - courses throughout school, including learning how to care for exotic critters! I have cared for my dogs from the puppy stage to the senior stage, so I am familiar with what each life stage brings. Although I have more experience with dogs, I still love cats and spending time with them just as much. I have lived with my current cat for 3 years, and she has taught me many things about cat behavior and companionship! I have an understanding and love for every animal, and I can’t wait to meet yours! I work full-time (with the flexibility to step away for a quick drop-in) from 6am to 2-3pm Monday thru Thursday, and Friday 6am-11am. I am free anytime after work, and my weekends are typically open! I will treat each client’s home and belongings with the upmost respect and care. Cleanliness is very important to me, so you can expect to return to a clean and tidy living space. I will ensure that your pet will remain in a safe and healthy home while you are away. Leaving a pet with someone else can be scary, so I want to make the experience for the owner and the pet as peaceful and pleasant as possible.

Sitter Profile Image: Lynne O.
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Lynne O.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 16 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: Michelle S.
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Michelle S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 139 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

“Michelle did a great job watching my golden doodle! She made sure to ask lots of questions about his feeding and walking schedule and sent me daily pictures and updates during her stay. I would absolutely ask her to watch Vash again!”

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Kastyn M.
Sitter Profile Image: christopher W.
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christopher W.
from
$60
per night
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 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 pet requires. 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: Austin M.
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Austin M.
Star Sitter
from
$65
per night
4.6 out of 5 stars
• 13 reviews
2 repeat clients
29 years of experience
Park Ridge, Madison, WI, 53719

About: Caring for dogs isn't just something I do. It's something I'm genuinely passionate about. I have experience caring for dogs of all ages, personalities, and energy levels, from young puppies learning routines to senior dogs who need a little extra patience and attention. I understand that every dog is different, and I take the time to get to know each pet's unique needs. I'm comfortable with feeding schedules, administering oral medications, crate training, basic puppy training, leash walking, playtime, and providing plenty of love and attention. I'm also attentive to changes in behavior or health and believe it's important to catch anything unusual early and communicate it with owners right away. I know how stressful it can be to leave your pet with someone else, so I make it my priority to provide a safe, clean, and calm environment where they feel comfortable. Whether your dog loves long walks, playing fetch, or simply relaxing with company, I'll make sure they receive the care and attention they deserve. Communication is very important to me. I'll provide regular updates, photos, and messages so you can enjoy your time away knowing your pet is in good hands. My goal is to care for every pet as if they were my own and give owners complete peace of mind. Pet care is already a major part of my daily routine. My day is structured around caring for dogs, so adding walks, drop-in visits, daycare, or boarding fits naturally into my schedule. Because I'm already following consistent routines for feeding, exercise, potty breaks, playtime, and cleaning, I'm able to provide dependable, attentive care throughout the day. I have a flexible schedule that allows me to give pets the time and attention they deserve rather than leaving them alone for long periods. Whether your pet needs a consistent routine, extra exercise, medication, or simply companionship, I'm committed to making sure they feel safe, comfortable, and well cared for while you're away. Safety and comfort are my top priorities when caring for pets, whether in my home or a client’s home. I make sure every pet is in a clean, secure, and calm environment where they can feel relaxed and stress-free. I follow each pet’s routine closely, including feeding schedules, potty breaks, exercise, and any special instructions provided by the owner. I pay close attention to behavior and overall well-being so I can quickly notice if something seems off and communicate right away. In my care, pets are never left unattended for long periods. I supervise interactions, provide structured playtime, and ensure a safe environment at all times—especially when introducing pets to new surroundings or other animals. I also respect the client’s home fully when providing in-home care, keeping everything clean, secure, and exactly as I found it. I understand how important trust is when someone allows you to care for their pet or enter their home, and I take that responsibility seriously. My goal is to make sure pets feel safe, loved, and comfortable, while giving owners complete peace of mind through clear communication and reliable care.

Sitter Profile Image: Teagan R.
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Teagan R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 100 reviews
31 repeat clients
12 years of experience
Westmorland, Madison, WI, 53711

“Have had Teagan stay with our two pups a few times and we always come home to happy pups and a spotless house. Great communication and lots of pictures.”

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Hanna E.
Sitter Profile Image: Meta M.
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Meta M.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 54 reviews
11 repeat clients
25 years of experience
Verona, WI, 53593

“Meta did a fantastic job dog sitting our large dog for over a week while we were away. She handled all of our dog’s medication, feeding, and walking, and took her into daycare on the days where she needed a little more exercise. She shared daily updates, was super responsive, and when we needed to make a last-minute change during our trip, she was supportive, and did what she could to make things as easy as possible when we returned. She took excellent care of our dog and our house and we’d love to work with her in the future!”

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Michael A.
Sitter Profile Image: Ruby K.
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Ruby K.
from
$64
per night
5.0 out of 5 stars
• 30 reviews
7 repeat clients
7 years of experience
Madison, WI, 53704

“Ruby did a great job taking care of our two labrador puppies (9 weeks and 9 months old). The pups seemed very happy and content when we came home.”

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Ben D.
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

“Tatyana is great with our dog. She was very understanding to a last minute change. Communication is great! Sent pictures and updates after her visits. Highly recommend.”

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Rhonda S.
Sitter Profile Image: Lauren R.
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Lauren R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 19 reviews
7 repeat clients
16 years of experience
Verona, WI, 53593

“Lauren was great! I felt very comfortable leaving our kitty in her care and she got the attention and meds she needed while we were away. We'd love to have Lauren back!”

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Lauren M.
Sitter Profile Image: Jessica B.
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Jessica B.
from
$35
per night
5.0 out of 5 stars
• 17 reviews
1 repeat client
10 years of experience
Madison, WI, 53719

“Jessica was very communicative. She sent updates twice daily with photos. Jessica took great care of Olive & our home. We’d be happy to book her again!”

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Amber F.
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: Camille M.
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Camille M.
from
$55
per night
4.9 out of 5 stars
• 56 reviews
25 repeat clients
15 years of experience
Tenney-Lapham, Madison, WI, 53713

“Camille did a wonderful job caring for our very active puppy! Took her for multiple walks even in the terrible WI spring weather! She also did well giving her medicine for some tummy troubles. Our home was left very clean too. Will not hesitate to have her again!”

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Janell D.
Sitter Profile Image: Taylor E.
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Taylor E.
from
$70
per night
5.0 out of 5 stars
• 25 reviews
7 repeat clients
7 years of experience
Madison, WI, 53705

“Taylor was a great sitter for our two dogs. She was respectful and responsive and willing to video chat with me before she came to watch them. We would definitely book her again!”

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Miranda H.
Sitter Profile Image: Ashley H.
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Ashley H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 23 reviews
4 repeat clients
7 years of experience
Madison, WI, 53716

“Ashley was wonderful - came all the way to us for a meet and greet and gave good vibes right away. Before our event, she came on time and provided updates and we felt very reassured. Our pup also loved her right away. Would recommend!”

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Rachel M.
Sitter Profile Image: Chelsea G.
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Chelsea G.
from
$45
per night
5.0 out of 5 stars
• 9 reviews
3 repeat clients
23 years of experience
Middleton, WI, 53562

“Chelsea was great! She sent daily updates with pictures, and the dogs seemed to love her!”

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Ryan P.
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The median cost per night for house sitting in Oakbridge is $50

Pet parents share their Rover experiences - Oakbridge

1 / 1
5.0 out of 5 stars

We've been having Annalesse watch our 15 yr old beagle for the last two major trips we've taken, and we've never been more at ease. It's been a journey to find a reliable, caring, and clean, communicative sitter and she's been an absolute blessing to work with. The house is always spotless and doesn't even look like anything has been touched when we return. We get updates and pictures without having to ask and she willingly cleans up any mess our pup makes which unfortunately happens more often with her old age. On our last trip we weren't returning until late and we were so impressed that made efforts to adjust her schedule just so that our girl wouldn't have to be alone longer than she needed to be. Consider yourself lucky if you have Annalesse watching your furry loved ones❤️

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Kelly R.
House Sitting
5.0 out of 5 stars

Other than just being a wonderful person, Stephany took incredible care of my pup and home. She was super responsive, always sent me pictures, and my house was in better condition than how I left it. So thankful to have found her!

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Janette B.
House Sitting
5.0 out of 5 stars

Quinn is great. Our girl Freddie has the best time and we are so thankful she gets to stay comfy in her own home with Quinn taking care of her!

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Sydney L.
House Sitting
5.0 out of 5 stars

Ann was very responsive and sent us many updates. She followed our cats complex feeding regimen perfectly while we were away. Highly recommend!

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Caitlin R.
House Sitting
5.0 out of 5 stars

Zach took excellent care of Tofu, was very responsive, and sent helpful updates (with great pictures and videos). Highly recommend!!

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Junko T.
House Sitting
5.0 out of 5 stars

Elizabeth was wonderful!! Shared a lot of pictures and made us feel very comfortable leaving out pups with her. Will absolutely be using her again. Highly recommended!!

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Adam D.
House Sitting
5.0 out of 5 stars

Mandi was great with our dog. She was punctual and friendly. Our pup loved her (loves everyone though haha). She kept us updated throughout the evening while we were gone with pictures and messages. She comforted our pup when people were letting off fireworks unexpectedly. Would hire again!

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Matthew K.
House Sitting
5.0 out of 5 stars

She was amazing with our dogs! Such a delight to find her and hope she will consider working with us again in the future!

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Kristin M.
House Sitting
5.0 out of 5 stars

Grace did a great job with the dogs! She sent periodic pictures and let me know of any issues. The dogs seemed really happy when we got home!

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Lisa N.
House Sitting
5.0 out of 5 stars

Briana did a great job staying with our dog and taking care of him. Home was tidy when we arrived home. She gave us updates and pictures as well.

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Teresa F.
House Sitting
5.0 out of 5 stars

Jesse sat for our 2 kitties for 3 weeks! She was absolutely fabulous! Regular check-ins, going the extra mile in every way to make the cats happy and making us feel comforted that she was taking tender loving care of them. She sent pics frequently and was conscientious about their meds and habits. Don’t hesitate to Grab Jesse she is a gem!!!

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Terri & Jeffrey H.
House Sitting
5.0 out of 5 stars

Jenna was an amazing sitter for Muller! He was a happy guy who got to play a ton of fetch. We received lots of updates and picture. We will definitely use Jenna again!

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Laurel S.
House Sitting
5.0 out of 5 stars

Jennifer was a fantastic sitter for our older dog! Communication was great, she updated us with lots of pictures, and she left the house perfectly clean. We hope we can have her stay with our dog in the future!

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Celia B.
House Sitting
5.0 out of 5 stars

Poorna did an incredible job overnight sitting for our two dogs, Chopper and Ophelia, while we were away on vacation. She provided lots of updates and many great pics of them while we were away unprompted, and was an amazing guest in our house as well. We would recommend her to anyone and will be booking with her in the future.

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Jace M.
House Sitting
5.0 out of 5 stars

We felt very comfortable leaving our 2 puppies in the care of Mara and Dirk. They communicated with us daily and handled them like pros. Would highly recommend - they quickly created a bond with our pups and were very caring and responsible.

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Broni W.
House Sitting
5.0 out of 5 stars

Austin took great care of our bulldog, Uecker and provided us updates throughout about how he was doing!

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Allison B.
House Sitting
5.0 out of 5 stars

Amy took great care of my new puppy, and her passion for fur babies really shone through. She was communicative, attentive, and shared some fun photos with me while I was away. I would definitely use her again!

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Janice B.
House Sitting
5.0 out of 5 stars

Maddy was great. We have a Yellow Lab and an English Mastiff and Maddy did great with them! We will definitely have her back next time we are out of town!

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Mindy W.
House Sitting
5.0 out of 5 stars

Melvin stepped in on very short notice and took great care of my two big dogs. He stayed at the house and left it in great shape when he left. The dogs liked him and were in great shape when I got home. Thanks to Mel for saving the weekend for us.

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ann s.
House Sitting
5.0 out of 5 stars

Justine took good care of our two dogs and home while we were away for two weeks, including an unexpected necessary visit to the vet for one of our dogs. Highly recommend.

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Lauren L.
House Sitting
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