House Sitting in Woodland Hills, Madison, WI

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Top rated Woodland Hills house sitters

1 / 1
Sitter Profile Image: Julie A.
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Julie A.
from
$45
per night
5 out of 5.0 stars
12 reviews
1 repeat client
16 years of experience
Verona, WI, 53593

Julie took excellent care of our dogs and our home while we were gone for 5 days. She was very loving, caring and attentive to our dogs. She was excellent with communication and sending photos. She walked the dogs, gave them lots of love and attention and went above and beyond even supplying some more broth for our dog when the supply ran out! I highly recommend Julie!

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Jane W.
Sitter Profile Image: Katie T.
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Katie T.
Star Sitter
from
$55
per night
5 out of 4.9 stars
20 reviews
2 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Katie was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

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Susana S.
Sitter Profile Image: Kaitlyn B.
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Kaitlyn B.
Star Sitter
from
$40
per night
5 out of 5.0 stars
14 reviews
4 repeat clients
20 years of experience
Madison, WI, 53719

Kaitlyn was patient with my anxious dog and gave him the time and space he needed to warm up to her. It put me at ease knowing he and my two cats were in good hands while I was out of town. She also left my house spotless! Highly recommend.

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Sarah S.
Sitter Profile Image: Terry K.
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Terry K.
from
$60
per night
5 out of 5.0 stars
31 reviews
10 repeat clients
30 years of experience
Middleton, WI, 53562

Terry was amazing with my pup! She was timely, easy to communicate with and follow my instructions. She went above and beyond taking care of him which made me worry about him less while I was gone. Will definitely be booking her again!

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Carolyn H.
Sitter Profile Image: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5 out of 5.0 stars
59 reviews
19 repeat clients
3 years of experience
Midvale Heights Community, Madison, WI, 53711

Louisa always leaves my home as neat and clean as she found it, and takes good care of my cat, who is pretty demanding of attention. She does a great job of communicating and gives just the right amount of updates and pictures. This is the second time I have used Louisa for cat-sitting and I would definitely use her again!

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Judy B.
Sitter Profile Image: Lydia S.
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Lydia S.
from
$52
per night
5 out of 5.0 stars
115 reviews
36 repeat clients
10 years of experience
Middleton, WI, 53562

Lydia really stepped in when I needed her. She was not only flexible when I had a sitter that didn’t work out last minute, but she was very quick and clear with communication. She sent lots of pictures and my dog was very happy with her.

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Taylor J.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$75
per night
5 out of 5.0 stars
48 reviews
18 repeat clients
10 years of experience
Madison, WI, 53719

Great experience with Ann watching our dogs and house for two nights. Very responsible, shared updates with photos, would hire again without hesitation.

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Benjamin L.
Sitter Profile Image: Erika K.
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Erika K.
from
$45
per night
5 out of 5.0 stars
8 reviews
12 years of experience
Middleton, WI, 53562

Erika was great! Curly, my dog, was well taken care of and so was my apartment! She did a great job following all my care instructions for my senior dog and she did a great job keeping everything very tidy. I would certainly recommend her to others and will use her again!

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Micha M.
Sitter Profile Image: Sidney R.
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Sidney R.
Star Sitter
from
$50
per night
5 out of 5.0 stars
49 reviews
15 repeat clients
20 years of experience
Middleton, WI, 53562

She did a wonderful job. Sent daily updates and respected the house. Even delt with my nosy neighbor. Will be using her for future dog sitting!

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Jessica S.
Sitter Profile Image: Alexandria P.
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Alexandria P.
Star Sitter
from
$39
per night
5 out of 5.0 stars
17 reviews
5 repeat clients
11 years of experience
Regent, Madison, WI, 53726

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.

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Jenifer S.
Sitter Profile Image: Corey N.
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Corey N.
from
$50
per night
5 out of 5.0 stars
8 reviews
2 repeat clients
20 years of experience
Madison, WI, 53705

Corey was amazing! Communication was on point from the very beginning of the booking process and only got better from there. It was very clear - even from the initial meet and greet with our pets - that Corey is a huge animal lover. Both our pup and our cat seemed to have a great weekend. And we got lots of updates (photo and otherwise). I’ve been trying to get my husband to let me find someone we are comfortable having keep our furry kiddos from getting lonely when we’re gone - and Corey exceeded all of our expectations with flying colors. We will definitely be counting on Corey again! Thank you!!

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Morgan Chelsea D.
Sitter Profile Image: Annie J.
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Annie J.
Star Sitter
from
$55
per night
5 out of 5.0 stars
48 reviews
17 repeat clients
6 years of experience
Midvale Heights Community, Madison, WI, 53711

Annie took great care of our dog and guinea pig! She gave me frequent updates and was very attentive to our anxious dog’s needs. Thank you!!!

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Genevieve H.
Sitter Profile Image: Sarah T.
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Sarah T.
from
$45
per night
5 out of 5.0 stars
7 reviews
5 repeat clients
2 years of experience
Madison, WI, 53719

We had a last minute need and Sarah came through for us. She even adjusted her own schedule to make it work! Would definitely have her come again!

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Kim K.
Sitter Profile Image: Hannah I.
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Hannah I.
Star Sitter
from
$50
per night
5 out of 5.0 stars
96 reviews
31 repeat clients
5 years of experience
Madison, WI, 53719

Hannah was great and we are so glad she was available to take care of our brood while we were gone. She took our dog on many walks and provided lots of updates to us. Our dog had some medical stuff come up between when she’d first met him/agreed to sit and when we left and she was super flexible in coming over to learn how to care for him and in being able and willing to administer medication to him while we were gone. It definitely put our minds at ease to know how things were going. Great communication, super friendly. Will definitely rebook with Hannah when we’re headed out of town again!

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Jen C.
Sitter Profile Image: Robert N.
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Robert N.
Star Sitter
from
$58
per night
5 out of 5.0 stars
111 reviews
35 repeat clients
20 years of experience
Orchard Ridge Community, Madison, WI, 53711

Robert did a great job watching Sadie while we were out of the country for a week. He sent updates every day along with pictures. She looked so happy on her walks and when he was just hanging out with her. I recommend Robert!

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Bethany P.
Sitter Profile Image: McKenna B.
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McKenna B.
from
$35
per night
20 years of experience
Madison, WI, 53711

About: I grew up on a farm here in Dane County and have experience looking after many species: large animal, small animal, fish, reptiles, birds, and of course cats and dogs! I have officially been petsitting since 2018 but have watched the pets of friends and family much longer than that. I received my degree in Animal and Veterinary Biosciences from UW Madison in 2023 with an emphasis in nutrition, and I worked at a pet food store for 6 years previous to that, so I am happy to accommodate any special feeding requests. I own two large protection breed dogs myself, but have also owned and petsat small breed dogs, so I have no size or breed exception. I am happy to work with reactive dogs as long as you help me to have a thorough understanding of what scares/upsets them. Please reach out to me if you have any questions! I am happy to do overnights, stay long term, or do just quick drop ins. I currently am working 8:30-5 M-F so I am typically unavailable during those hours. I am happy to do overnights, long term stays, drop in visits, or walks I make sure to go over all of the owners requests and requirements and to follow all rules. I am clean and tidy and will leave your house as I found it.

Sitter Profile Image: Grace H.
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Grace H.
from
$45
per night
5 out of 5.0 stars
23 reviews
4 repeat clients
6 years of experience
Madison, WI, 53711

Grace is an awesome dog sitter! She is very communicative, respectful, and most importantly, loves dogs. She stayed at our house to watch our dog, Scout, and I came home to a very happy dog even though he usually has separation anxiety. Couldn't recommend Grace enough!

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Sarah L.
Sitter Profile Image: Corinne B.
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Corinne B.
from
$60
per night
5 out of 5.0 stars
18 reviews
6 repeat clients
25 years of experience
Madison, WI, 53719

Corinne is amazing!! She watched over our two "boys" (greyhounds) and took such thoughtful care of them! We got lots of pictures and updates while we were away and the peace of mind that offers to know that your loved ones are cared for while you are away is truly priceless! Not to mention that she is very respectful of our home and had everything cleaned and tidied as if we were never gone! Gosh, thanks so much!!!

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Elliot S.
Sitter Profile Image: James S.
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James S.
from
$40
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
30 years of experience
Middleton, WI, 53562

Thanks James for taking excellent care of Maserati! He was happy and healthy for our visit even thought he had some complicated health issues with his old age. James took care of our house and dog amazingly! Thank you!

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Meghann K.
Sitter Profile Image: Anna H.
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Anna H.
from
$65
per night
5 out of 5.0 stars
27 reviews
7 repeat clients
7 years of experience
Middleton, WI, 53562

Anna is a fantastic dog sitter who goes above and beyond for her clients. Before having Anna sit for us for the first time, she made the effort to come by and visit our pup. This was so important for there reasons: 1. Gave our pup the opportunity to become friends with Anna; 2. Allowed our dog to feel comfortable in her home with this new friend; and 3. Gave us the opportunity to show Anna where the important things for our dog are in the house. Anna is prompt and communicative. She gave us photo and text updates throughout her visit. She is clearly a kind and respectful person and dogs seem to love her immediately. I will most definitely reach out to Anna again for any dog sitting/house sitting occasions.

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Lesli M.
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Sitter Profile Image: Julie A.
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Sitter Profile Image: Julie A.
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1. Julie A.

Mature, skilled and flexible
Verona, WI, 53593
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
12 reviews
1 repeat client
Profile image

Julie took excellent care of our dogs and our home while we were gone for 5 days. She was very loving, caring and attentive to our dogs. She was excellent with communication and sending photos. She walked the dogs, gave them lots of love and attention and went above and beyond even supplying some more broth for our dog when the supply ran out! I highly recommend Julie!

Availability updated 3 days ago
Sitter Profile Image: Katie T.
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Sitter Profile Image: Katie T.
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2. Katie T.

Star Sitter
ACTIVE, FLEXABLE, DOG LOVER
Marquette, Madison, WI, 53703
6.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 4.9 stars
20 reviews
2 repeat clients
Profile image

Katie was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

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

Star Sitter
Your Go-To Sitter
Madison, WI, 53719
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
14 reviews
4 repeat clients
Profile image

Kaitlyn was patient with my anxious dog and gave him the time and space he needed to warm up to her. It put me at ease knowing he and my two cats were in good hands while I was out of town. She also left my house spotless! Highly recommend.

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

Rover 101
Grandma love is on the way !!
Middleton, WI, 53562
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
31 reviews
10 repeat clients
Profile image

Terry was amazing with my pup! She was timely, easy to communicate with and follow my instructions. She went above and beyond taking care of him which made me worry about him less while I was gone. Will definitely be booking her again!

Availability updated 2 days ago
Sitter Profile Image: Louisa M.
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Sitter Profile Image: Louisa M.
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5. Louisa M.

Star Sitter
Your pet’s new friend! 🐶🐱🐰🐔🐠
Midvale Heights Community, Madison, WI, 53711
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
59 reviews
19 repeat clients
Profile image

Louisa always leaves my home as neat and clean as she found it, and takes good care of my cat, who is pretty demanding of attention. She does a great job of communicating and gives just the right amount of updates and pictures. This is the second time I have used Louisa for cat-sitting and I would definitely use her again!

Availability updated 6 days ago
Sitter Profile Image: Lydia S.
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Sitter Profile Image: Lydia S.
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6. Lydia S.

Here to help with your schedule
Middleton, WI, 53562
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$52
per night
5 out of 5.0 stars
115 reviews
36 repeat clients
Profile image

Lydia really stepped in when I needed her. She was not only flexible when I had a sitter that didn’t work out last minute, but she was very quick and clear with communication. She sent lots of pictures and my dog was very happy with her.

Availability updated 19 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Ann A.
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Sitter Profile Image: Ann A.
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7. Ann A.

Star Sitter
Attentive and reliable pet sitter
Madison, WI, 53719
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
48 reviews
18 repeat clients
Profile image

Great experience with Ann watching our dogs and house for two nights. Very responsible, shared updates with photos, would hire again without hesitation.

Availability updated today
Sitter Profile Image: Erika K.
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Sitter Profile Image: Erika K.
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8. Erika K.

Loving care for your furry family
Middleton, WI, 53562
1.6 mi. away
House Sitting
from
$45
per night
5 out of 5.0 stars
8 reviews
Profile image

Erika was great! Curly, my dog, was well taken care of and so was my apartment! She did a great job following all my care instructions for my senior dog and she did a great job keeping everything very tidy. I would certainly recommend her to others and will use her again!

Availability updated 2 days ago
Sitter Profile Image: Sidney R.
Verified Enhanced Background Check
Sitter Profile Image: Sidney R.
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9. Sidney R.

Star Sitter
They call me “The Pal Gal”!
Middleton, WI, 53562
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
49 reviews
15 repeat clients
Profile image

She did a wonderful job. Sent daily updates and respected the house. Even delt with my nosy neighbor. Will be using her for future dog sitting!

Availability updated 5 days ago
Sitter Profile Image: Alexandria P.
Verified Enhanced Background Check
Sitter Profile Image: Alexandria P.
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10. Alexandria P.

Star Sitter
G.O.A.T. pet-sitter!
Regent, Madison, WI, 53726
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$39
per night
5 out of 5.0 stars
17 reviews
5 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 6 days ago
Sitter Profile Image: Corey N.
Verified Enhanced Background Check
Sitter Profile Image: Corey N.
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11. Corey N.

Compassionate Care for All!
Madison, WI, 53705
1.8 mi. away
House Sitting, Drop-In Visits
from
$50
per night
5 out of 5.0 stars
8 reviews
2 repeat clients
Profile image

Corey was amazing! Communication was on point from the very beginning of the booking process and only got better from there. It was very clear - even from the initial meet and greet with our pets - that Corey is a huge animal lover. Both our pup and our cat seemed to have a great weekend. And we got lots of updates (photo and otherwise). I’ve been trying to get my husband to let me find someone we are comfortable having keep our furry kiddos from getting lonely when we’re gone - and Corey exceeded all of our expectations with flying colors. We will definitely be counting on Corey again! Thank you!!

Availability updated yesterday
Sitter Profile Image: Annie J.
Verified Enhanced Background Check
Sitter Profile Image: Annie J.
Verified Enhanced Background Check

12. Annie J.

Rover 101
Star Sitter
Active & communicative pet lover!
Midvale Heights Community, Madison, WI, 53711
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
48 reviews
17 repeat clients
Profile image

Annie took great care of our dog and guinea pig! She gave me frequent updates and was very attentive to our anxious dog’s needs. Thank you!!!

Availability updated yesterday
Sitter Profile Image: Sarah T.
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Sitter Profile Image: Sarah T.
Verified Enhanced Background Check

13. Sarah T.

Trustworthy, available pet lover!
Madison, WI, 53719
1.7 mi. away
House Sitting, Drop-In Visits
from
$45
per night
5 out of 5.0 stars
7 reviews
5 repeat clients
Profile image

We had a last minute need and Sarah came through for us. She even adjusted her own schedule to make it work! Would definitely have her come again!

Availability updated over 1 year ago
Sitter Profile Image: Hannah I.
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Sitter Profile Image: Hannah I.
Verified Background Check

14. Hannah I.

Rover 101
Star Sitter
Dogs love to run and play with me!
Madison, WI, 53719
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
96 reviews
31 repeat clients
Profile image

Hannah was great and we are so glad she was available to take care of our brood while we were gone. She took our dog on many walks and provided lots of updates to us. Our dog had some medical stuff come up between when she’d first met him/agreed to sit and when we left and she was super flexible in coming over to learn how to care for him and in being able and willing to administer medication to him while we were gone. It definitely put our minds at ease to know how things were going. Great communication, super friendly. Will definitely rebook with Hannah when we’re headed out of town again!

Availability updated 12 days ago
Sitter Profile Image: Robert N.
Verified Enhanced Background Check
Sitter Profile Image: Robert N.
Verified Enhanced Background Check

15. Robert N.

Star Sitter
I'll do the walking!
Orchard Ridge Community, Madison, WI, 53711
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$58
per night
5 out of 5.0 stars
111 reviews
35 repeat clients
Profile image

Robert did a great job watching Sadie while we were out of the country for a week. He sent updates every day along with pictures. She looked so happy on her walks and when he was just hanging out with her. I recommend Robert!

Availability updated 10 days ago
Sitter Profile Image: McKenna B.
Verified Enhanced Background Check
Sitter Profile Image: McKenna B.
Verified Enhanced Background Check

16. McKenna B.

Reliable, Responsible, and Fun!
Madison, WI, 53711
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
3 reviews

Having previously worked with McKenna is have seen both her interactions with dogs in a pet store environment as well as with my own dog. She has a outgoing demeanor that helps nervous dogs like mine grow comfortable in her presence.

Availability updated 2 days ago
Sitter Profile Image: Grace H.
Verified Enhanced Background Check
Sitter Profile Image: Grace H.
Verified Enhanced Background Check

17. Grace H.

Dogs are a girl’s best friend!
Madison, WI, 53711
3.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
23 reviews
4 repeat clients
Profile image

Grace is an awesome dog sitter! She is very communicative, respectful, and most importantly, loves dogs. She stayed at our house to watch our dog, Scout, and I came home to a very happy dog even though he usually has separation anxiety. Couldn't recommend Grace enough!

Availability updated today
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check

18. Corinne B.

Animal Lover
Madison, WI, 53719
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
18 reviews
6 repeat clients
Profile image

Corinne is amazing!! She watched over our two "boys" (greyhounds) and took such thoughtful care of them! We got lots of pictures and updates while we were away and the peace of mind that offers to know that your loved ones are cared for while you are away is truly priceless! Not to mention that she is very respectful of our home and had everything cleaned and tidied as if we were never gone! Gosh, thanks so much!!!

Availability updated 2 days ago
Sitter Profile Image: James S.
Verified Background Check
Sitter Profile Image: James S.
Verified Background Check

19. James S.

Dependable, Experienced and Loving!
Middleton, WI, 53562
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

Thanks James for taking excellent care of Maserati! He was happy and healthy for our visit even thought he had some complicated health issues with his old age. James took care of our house and dog amazingly! Thank you!

Availability updated 66 days ago
Sitter Profile Image: Anna H.
Verified Enhanced Background Check
Sitter Profile Image: Anna H.
Verified Enhanced Background Check

20. Anna H.

The best care for your best friend!
Middleton, WI, 53562
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
27 reviews
7 repeat clients
Profile image

Anna is a fantastic dog sitter who goes above and beyond for her clients. Before having Anna sit for us for the first time, she made the effort to come by and visit our pup. This was so important for there reasons: 1. Gave our pup the opportunity to become friends with Anna; 2. Allowed our dog to feel comfortable in her home with this new friend; and 3. Gave us the opportunity to show Anna where the important things for our dog are in the house. Anna is prompt and communicative. She gave us photo and text updates throughout her visit. She is clearly a kind and respectful person and dogs seem to love her immediately. I will most definitely reach out to Anna again for any dog sitting/house sitting occasions.

Availability updated today

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