House Sitting in Oakwood Village, Madison, WI

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Ann V.
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Sitter Profile Image: Ann V.
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1. Ann V.

Animal Lover and Law Student
Madison, WI, 53711
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
39 reviews
8 repeat clients
Profile image

Ann was amazing. Detailed updates every day, kept my house SO clean, excellent communicator, and my elderly cat with several medication needs was so well taken care of. Would rebook again and again!

Availability updated yesterday
Sitter Profile Image: Louisa M.
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Sitter Profile Image: Louisa M.
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2. Louisa M.

Your pet’s new friend! 🐶🐱🐰🐔🐠
Madison, WI, 53711
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
41 reviews
14 repeat clients
Profile image

Louisa and Sammy were absolutely wonderful with my puppy and cat. I received frequent updates and photos. Louisa was especially attendant to my puppy who wasn’t feeling well. I would recommend them to anyone looking for pet care and I will be thinking of Louisa first when I next need them to be cared for.

Availability updated 23 days ago
Sitter Profile Image: Aurora R.
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Sitter Profile Image: Aurora R.
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3. Aurora R.

Your Dog's Best Friend
Madison, WI, 53705
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
14 reviews
2 repeat clients
Profile image

Aurora continues to be an incredible sitter. Our dog Ollie is always calm and well taken care of whenever we return home. We are given updates regularly, I can't recommend Aurora enough!

Availability updated yesterday
Sitter Profile Image: Robert N.
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Sitter Profile Image: Robert N.
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4. Robert N.

I'll do the walking!
Orchard Ridge Community, Madison, WI, 53711
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
5.0 out of 5 stars
53 reviews
17 repeat clients
Profile image

He and one of my girls hit it off! Good communication throughout the stay. He took great care of my girls including administering meds and wrapping a foot too!

Availability updated yesterday
Sitter Profile Image: kylie l.
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Sitter Profile Image: kylie l.
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5. kylie l.

can’t wait to meet your dogs!
Madison, WI, 53719
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
Profile image

Kylie was quick to respond to our texts and sent us the most adorable pics of our pup so we could see how happy he was. We will definitely be hiring her again.

Availability updated 2 days ago
Sitter Profile Image: Alexandria P.
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Sitter Profile Image: Alexandria P.
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6. Alexandria P.

G.O.A.T. pet-sitter!
Regent, Madison, WI, 53726
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
15 reviews
3 repeat clients
Profile image

I am incredibly grateful to Alexandria for watching my dog, Topi. She is not only kind and pleasant, but she genuinely cares for Topi’s well-being. Alexandria went above and beyond to ensure Topi was happy and comfortable. Her attentive and loving nature truly sets her apart. I highly recommend her to anyone in need of a trustworthy and compassionate pet sitter.

Availability updated yesterday
Sitter Profile Image: Travis M.
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Sitter Profile Image: Travis M.
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7. Travis M.

Reliable, caring dog-lover
MONONA, WI, 53713
7.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
Profile image

Travis did a great job with our two dogs and cat! He was very attentive and caring to our animals, which we greatly appreciated. He sent us pictures and kept in touch with us daily too, which we asked for and loved. He was also very responsible at our home and left it in the same condition in which he found it. Highly recommend and will hire him again.

Availability updated 4 days ago
Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
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8. Sarah W.

Pet lover with vet assistant exp.
Madison, WI, 53704
7.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$42
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
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She was so great at sending photos and updates without even asking. You can tell she tries to get to know the dog and really care for them. Highly recommend!

Availability updated yesterday
Sitter Profile Image: Anna H.
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Sitter Profile Image: Anna H.
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9. Anna H.

The best care for your best friend!
Middleton, WI, 53562
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$58
per night
5.0 out of 5 stars
24 reviews
7 repeat clients
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Anna did an excellent job with our dogs. Just the right amount of communication for our tastes. We will definitely ask her to sit for us again!

Availability updated today
Sitter Profile Image: Ann A.
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Sitter Profile Image: Ann A.
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10. Ann A.

Attentive and reliable pet sitter
Madison, WI, 53719
3.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$56
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
Profile image

Ann was very friendly and good with our pets. She sent lots of updates with pictures.

Availability updated yesterday
Sitter Profile Image: Kaitlyn B.
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Sitter Profile Image: Kaitlyn B.
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11. Kaitlyn B.

Your Go-To Sitter
Madison, WI, 53719
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5.0 out of 5 stars
3 reviews
1 repeat client
Profile image

Kaitlyn was an absolute sweetheart and such a great communicator! Prior to our first booking, she asked thoughtful questions about what she could do to prepare and be well-informed, which I appreciated. She sent me photos and updates while caring for Princeton and also gave me a great recap after I got home. I highly recommend Kaitlyn and will definitely book her again!

Availability updated today
Sitter Profile Image: Ila K.
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Sitter Profile Image: Ila K.
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12. Ila K.

I am passionate about pooches!
Fitchburg, WI, 53713
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$26
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
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Ila was amazing with our boys and our house was in perfect condition when we came home. She went above and beyond and took extra care of our plants and sent so many pictures! Will definitely have her again!

Availability updated today
Sitter Profile Image: Terry K.
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Sitter Profile Image: Terry K.
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13. Terry K.

Grandma love is on the way !!
Middleton, WI, 53562
3.0 mi. away
House Sitting, Drop-In Visits
from
$50
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
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Terry was amazing with my dogs. She sent cute pictures, kept me updated, and took them for a couple walks a day. When I came home, I was surprised that my bed had new sheets on it and she had washed the ones that were on the bed. She also made sure the house was clean. Counters were washed off, dishes were in the dishwasher and more. I would definitely recommend booking with Terry.

Availability updated yesterday
Sitter Profile Image: Robert C.
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Sitter Profile Image: Robert C.
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14. Robert C.

Home is where the bark is
Fitchburg, WI, 53711
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$36
per night
5.0 out of 5 stars
145 reviews
50 repeat clients
Profile image

Robert was fantastic as usual! He stayed at our house and watched our pups for a long weekend, and they are absolutely happy and exhausted. Thank you Robert!

Availability updated today
Sitter Profile Image: Andrew L.
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Sitter Profile Image: Andrew L.
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15. Andrew L.

Rover 101
Looking for a fur baby to love! 💜
Madison, WI, 53715
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$89
per night
5.0 out of 5 stars
134 reviews
51 repeat clients
Profile image

“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 day of special outings, and cuddles. We missed her so much but we knew she was being cared for and loved while we were away. Through text exchange, drew told us things about our girl that only someone who was invested in her would pick up on. We feel so grateful to have found Drew and will definitely ask him to take care of her again!!

Availability updated today
Sitter Profile Image: Rachael T.
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Sitter Profile Image: Rachael T.
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16. Rachael T.

Caring Veterinary Assistant
Madison, WI, 53719
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5.0 out of 5 stars
3 reviews

Rachael has watched our dogs for several years now. She is very professional, responsible and will love your fur baby(ies) as her own. Rachael is very reliable and trustworthy. Anytime we are out of town and Rachael is at our house I know I don't have to worry about anything. She checks in with us to let us know how everything is going. Rachael is the one who you want to use as your dog sitter, giving you peace of mind while you are away.

Availability updated 3 days ago
Sitter Profile Image: Melissa H.
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Sitter Profile Image: Melissa H.
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17. Melissa H.

Your Fur-Baby's Best Auntie!
Allied Community, Fitchburg, WI, 53711
2.9 mi. away
Boarding, House Sitting
from
$60
per night
5.0 out of 5 stars
16 reviews
7 repeat clients
Profile image

She was great with my dog and very communicative. I would sit with her again without hesitation.

Availability updated today
Sitter Profile Image: Shinduri V.
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Sitter Profile Image: Shinduri V.
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18. Shinduri V.

Your pets favorite aunt!
Madison, WI, 53717
2.0 mi. away
Boarding, House Sitting
from
$40
per night
5.0 out of 5 stars
8 reviews
Profile image

Shinduri was just wonderful. She has a pup of her own and clearly loves dogs. She was comfortable with Finn as soon as she met him (and he’s an overenthusiastic jumper). She sent us pictures each day, took him to the dog park and treated him as her own. We’re so grateful and will absolutely be using her in the future!

Availability updated 10 days ago
Sitter Profile Image: Stephany D.
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Sitter Profile Image: Stephany D.
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19. Stephany D.

I'll be your dog's other bestie!
madison, WI, 53705
1.5 mi. away
Boarding, House Sitting, Dog Walking
from
$38
per night
5.0 out of 5 stars
38 reviews
12 repeat clients
Profile image

Stephany was awesome with Gus and Goldie. She communicated often, sent pics and left the house just as she found it. Would definitely use her again.

Availability updated yesterday
Sitter Profile Image: Anna O.
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Sitter Profile Image: Anna O.
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20. Anna O.

Will treat your sweet pet as my own
Madison, WI, 53711
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
Profile image

Anna was very prompt at responding to messages and was great meeting my dogs who can be nervous with strangers. She was able to keep my dogs calm and content while I was away, I’d definitely recommend her!

Availability updated 5 days ago

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